Nomenclature of Organic Chemistry -1-

Chap. 1

INTRODUCTION TO THE STUDY

OF ORGANIC CHEMISTRY
CONTENT:
-2- Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We develop conditions of mutual collaboration and

active participation in students, through knowledge of
the oil zones in Bolivia through bibliographic research,
to raise awareness in the preservation and rational
exploitation of energy deposits.

MOLECULES IN 3D
To begin the study of Organic Chemistry, I suggest you visit an interesting page that
shows us molecules of some organic compounds in 3D (three dimensions), easy to
enter. Likewise, you can investigate other simulators, they are programs that have
been built to facilitate and accompany the study of the contents that the books have
and when there are no laboratories.

Educaplus.org is the personal site of Jesús Peñas Cano, professor of Physics and
Chemistry.

Quotes from the author: “The Educaplus.org project has been online since 1998
and its fundamental objective is to share with everyone, but fundamentally with the
Spanish-speaking educational community, the work that I have been doing to
improve my own professional practice as a teacher”

Procedure:

- Go to Google and type educaplus molecules in 3d , then click

- Select the page 3D Molecules, Elements educaplus.org
- In the top right tab select any molecule and observe on the screen, left click on
the window and move the mouse; The molecule will rotate and you will be able to
observe it in three dimensions.
Nomenclature of Organic Chemistry -3-

Historical development.- At the beginning of the - Their reactions are slow and rarely quantitative, the
19th century it was estimated that organic compounds amount of compounds
had the so-called vital force and that they could be acquaintances exceed a million.
synthesized only by living beings , but this concept
disappeared when, in 1828, the German Federico - Inorganic compounds are formed in most
Wohler (1800-1882) prepared a compound Known as elements of the periodic table, the type of bond
ammonium cyanate , when this substance was that predominates in them is ionic.
heated it transformed into white, silky crystals. When
performing some tests, it was found that they were - They are mainly solids, with a melting point greater
urea crystals (a substance obtained when urine than 400 ° C.
evaporates).
- In aqueous or molten solutions they conduct
This was a surprising change since ammonium electric current; They are fireproof,
cyanate is an inorganic compound , while urea is an
organic compound product of the activity of a living - Their reactions are fast, in the crystalline state or in
organism. solution they separate into ions, of which only a
few thousand are known.
Many carbon compounds are an important part of the
matter of which all living beings are made. A carbon The carbon atom.- Carbon only constitutes 0.08% of
compound is DNA, which is a giant molecule that the entire lithosphere, hydrosphere and atmosphere. It
contains genetic information. appears in the Earth's crust in the form of calcium
carbonate (CaCO 3 ) or magnesium (MgCO 3 ) rocks.
The clothes that human beings wear, whether made of
natural substances such as wool or cotton, or In the atmosphere we find it mainly in the form of
synthetic fibers such as nylon or polyester, are made carbon dioxide (CO 2 ) and carbon monoxide (CO).
up of carbon compounds. Many of the materials found
in homes, the gasoline that powers cars, the rubber in Natural state of carbon.- Carbon can be found in
tires, plastics, paints, cosmetics, etc. nature in crystalline and pure form, in this case there
are two allotropic forms, that is, with different
Almost all medications used in the treatment of properties, which are graphite and diamond .
diseases are of organic origin.
a) Graphite : It is the most stable allotropic form of
Any of the professional careers, in almost all biological carbon at ordinary temperature and pressure.
sciences, requires a solid foundation in organic
chemistry, since most biological processes require at - It is soft, black and slippery, with a density of 2.25
least some knowledge of it. g/cc.
- It is a good conductor of heat and electricity, it is
Concept.- A definition for organic chemistry is the used in electrodes, in electrometallurgy.
following: - Mixed with clay, graphite is found in the charcoal of
pencils
It is the science that studies the structure and - It crystallizes in shiny sheets, in a hexagonal
properties of carbon compounds that mainly shape.
constitute living matter, their application in - It is used in the manufacture of pencils, crucibles,
industry and technological development. etc.

Differences between organic and inorganic b) Diamond : Unlike graphite, diamond is one of the
compounds.- Among the most important differences hardest substances known.
are:

- Organic compounds contain carbon which may

be forming covalent bonds with hydrogen; sulfur,
nitrogen, oxygen, phosphorus, halogens and with
some metals forming ionic bonds.

- They are fuels, with exceptions such as CCl 4; They

are gases, liquids or solids with a melting point of
less than 400 ° C.

- They are usually insoluble in water; in solution or

melted form they do not conduct electric current.
-4- Nomenclature of Organic Chemistry

- It is colorless, does not conduct electricity and is b) Coal : It has 70 to 90% carbon and can contain up
denser than graphite, its density is 3.53 g/cc. to 45% volatile materials and is, from an industrial
- It is crystallized carbon and purer than all other point of view, the most interesting carbon. From coal,
carbons. by distillation in the absence of air, fuel gases,
- Crystallizes inthe system cubic , ordinarily ammonia gases, tar and 20% coke are obtained. By
in octahedra. distilling tar, a huge range of products are obtained
- In this structure very links are presented that have applications such as solvents, dyes,
strong withoutthat there is electrons weakly plastics, explosives and medicines.
retained.
- It has a point of fusion higher than c) Brown coal : Generally used as
known of an element is about 3570° C. fuel, contains 70% carbon.

d) Peat : It is the lowest cost coal as fuel. It is widely

DIAMOND used for the manufacture of cardboard. Peat contains
60% carbon.
Covalent carbon
bond atom Artificial state of carbon.- Carbon is found as a

GRAPHIT
E
carbon
atom

Weak bonding
forces

waste from certain industrial processes, for example:

coke , retort coal , vegetable charcoal , animal
charcoal and black smoke .

Covalent Most of them are good fuels, but they also have other
bond specific applications.

a) Coke : Residue from the dry distillation of coal. It is

light porous and gray in color. With great calorific
value, it is used in metallurgy as a fuel and reducer of
oxidized metals.

b) Retort coal : It is the carbon that remains

embedded in the interior walls of the retorts of gas
factories when distilling coal. It is hard and compact. It
has good thermal and electrical conductivity.

c) Charcoal : It is the residue of the dry distillation or

Carbon can also be found in nature in an amorphous pyrolysis of wood. It is very porous and contains a
state in four different minerals: anthracite , coal , great adsorption power (that is, thin layers of
lignite and peat . molecules of different substances can adhere to its
surfaces).
a) Anthracite : It is the richest in carbon 98% and
has 5 to 6% volatile materials, being the one with the
highest heating power.
Nomenclature of Organic Chemistry -5-

d) Animal charcoal : It is obtained from the “s” orbitals “p” orbitals

incomplete combustion of various animal remains, In industry, carbon black is obtained through the
mainly bones and blood. It is a very fine powder with incomplete combustion of natural gas, which contains
great adsorption power. It is used to decolorize dark methane (CH 4 ) according to the equation:
liquids.
CH 4 + O 2 —► 2H2O +C
e) Carbon black : Product of the incomplete Atomic orbitals are the regions around the nucleus
combustion of numerous organic compounds such as where electrons are most likely to be found.
resins, gauze, natural gas, or petroleum derivatives. It
is used for the manufacture of printing inks, carbon There are three forms of hybridization caused by
paper, shoe polishing ointment. Indian ink, etc. the different rearrangements of atomic orbitals: sp 3 ,
sp 2 and sp .
Structure of the carbon atom.- The carbon atom C = 1s 2 2s 2 2p 2
hybridization
presents three types of hybridizations to form a) Sp 3 (C–C single bond) .- One of the
compounds. electrons of the 2s orbital hybridizes with the 3 2p
orbitals to form 4 new hybrid orbitals that are oriented
Basal state and excited state of C.- Its electronic in space forming an angle of 109.5º between them
configuration in its natural state is: (tetrahedral).

It is the combination of:

3
1 s orbital + 3 p orbitals = 4 sp hybrid orbitals

12
6
1s 2s 2 2p
2 2

2s 2 2p 1
2p 2pz
1s
0
x 1
2
and
Electrons of the last energy level (L = 2)
It has been observed that in organic compounds, Hybrid state
Baseline
carbon is tetravalent , that is, it can form 4 bonds.
state → ↑
I3 □ ↑3 □ ↑ □ ↑
□
When this atom receives an external influence , one sp sp sp sp 3 3

of the electrons from the 2s orbital is transferred to s2 p x 1 p and 1

the 2p z orbital, and an excited state of the carbon pz
Carbon atom with sp 3 hybridization
atom is obtained due to the proximity of other atoms:

1s 2s 1 2p1 2p 1
2p1
12 y
2
x z
6c

Hybridizations of the carbon atom.- The

hybridization of the carbon atom consists of the
combination or arrangement of the pure atomic The new configuration of the hybridized carbon is
orbitals of the last energy level , to form more represented as:
stable hybrid orbitals.
-6- Nomenclature of Organic Chemistry

Electrons of the last energy level (L = 2)

22C = 152 2 ( sp 3) 2 ( ↑↓] I ↑ □ ↑ni → ↑□↑□↑□i↑□
P ) 2 ( SP 3 ) 2 ( sp
S
3 3
)1 s2 px1py1pz sp 2 sp 2 sp 2 p and
There are 2 unhybridized p orbitals left. The non-
hybridized orbitals remain perpendicular to the line
Each of the sp 3 hybrid orbitals of carbon can bond to formed by the 2 sp orbitals.
4 other atoms, thus explaining the tetravalence of
the carbon atom . 1 s + orbital 1 p orbital = 2 sp orbitals

b) Sp 2 hybridization (C=C double bond) .- One of the

electrons of the 2s orbital hybridizes with the 2 2p
orbitals to form 3 new hybrid orbitals that are oriented S Px
Q§-8Q SP SP
in a plane forming an angle of 120º between them, as
if they were directed towards the vertices of an
equilateral (triangular) triangle. Electrons of the last energy level
1 p orbital remains unhybridized. The unhybridized Baseline state Hybrid state
orbital is perpendicular to the plane of the 3 sp²
orbitals. ↑↓] I ↑ □ ↑II → ↑□↑□I↑1↑]
Carbon atom with sp hybridization
s2 px1py1pz sp sp p and p z
2
1 s orbital + 2 p orbitals = 3 sp orbitals The new configuration of the hybridized carbon is
represented as:
SP 2 SP 2 SP 2
Carbon atom with sp 2 hybridization ( sp ) 1 2p 1
y 2p 1
z

6C = 1s 2 1 ( sp ) 1 2

Molecular orbitals are formed by overlapping

atomic orbitals; these must have similar sizes and
Baseline Hybrid state energies, as well as appropriate spatial structures.
state
a) Sigma (σ ) molecular orbitals.- The atomic
orbitals overlap frontally and a single overlap of the
respective electronic clouds occurs. It has an axis of
symmetry with respect to the line that joins the two
nuclei.
The new configuration of the hybridized carbon is
represented as: A rotation with respect to said axis does not produce
any change.
6C = 1S 2
2 ( sp )
2
1 2

( sp )2
1 2

( S
P 2 J 2
P!

c) Sp hybridization (C≡C double bond) .- One of

the electrons of the 2s orbital hybridizes with 1 2p
orbital to form 2 new hybrid orbitals that are oriented
in a line forming an angle of 180º between them
(Linear).

Types of bonds.- Chemical bonds are also classified

according to the type of orbitals participating in the
bond, and their orientation in:

Sigma bond , (o) and Phi bond , (T)

Nomenclature of Organic Chemistry -7-

b) The double bond (C = C) .- They share two

pairs of electrons, it is formed when carbon atoms
join together with sp 2 hybridization.

(sp 2 = sp 2 ): They constitute a sigma bond and a

phi link .

c) Molecular orbitals d) The triple bond

pi (π) .- The atomic (C = C) .- They share
orbitals overlap three pairs of
laterally and two or electrons, it is formed
more overlaps of the when carbon atoms
respective electronic join together with sp
clouds occur. There is hybridization .
a nodal plane of
symmetry that includes (sp = sp): They
the nuclei. constitute one sigma
bond and two
phi
links .

π bond

A molecular orbital is on the type of

the more stable the hybridization present
greater the degree of in the carbon atoms: a)
overlap between the The single bond (C –
atomic orbitals that C) .- They share a pair
form it. of electrons, it is
formed when carbon
Molecular orbitals ( a ) atoms join together
are more stable than ( with sp 3 hybridization.
n ) because the
(sp 3 – sp 3 ): They
Example: constitute a sigma
bond.
Methane: CH
4

degree of overlap of
the "s" orbitals is
greater than that of the
"p" orbitals.

Bonds between
carbons.- Depending
-8- Nomenclature of Organic Chemistry

π bond elements (C, H, O, N)

through the sharing of
Properties of the electron pairs, forming
carbon atom.- covalent bonds.
Carbon has the
following chemical h
properties: ox
H%CxH
a) Covalence.- The OX
carbon atom h
combines with other Lewis notation
b) Tetravalence.- Carbon
is tetravalent, it forms a total
of four covalent bonds,
complying with the octet
rule.
h

°
Yo
oCo H __ C __ H
either
Yo
h
Lewis notation Methan
e
 Nomenclature of Organic Chemistry -9-

c) Self-saturation.- Carbon joins other carbon Each vertex is a carbon saturated with H
atoms to form carbon chains that can contain more
than 100 carbon atoms.

Yo Yo Yo II
–C –C –C –C –C –
Yo Yo Yo II
saturated chain 3,4-
Unsaturated chain
Representation of 2-
organic molecules.- Various formulas are used to methylpentane
represent the same molecule: dimethyl-2-pentene

a) Global or molecular formula.- Indicates the

total number of atoms that make up the molecule: Organic nomenclature.- There are two ways to
name organic compounds:
C 4 H 10 C3H6O
a) Systematic nomenclature.- The standards
butane acetone currently in force were agreed by the IUPAC
(International Union of Pure and Applied Chemistry)
in 1993.
b) Semi- developed formula.- In it the atoms that
bond to the same carbon atom appear grouped: These recommendations modify the previous ones
from 1979, the proposed changes are related to the
CH 3 – CH 2 – CH 2 – CH 3 CH 2 = CH – CH 2 – CH nomenclature of some compounds and basically
3 consist of placing the numerals that indicate the
position of the double or triple bond or of the
butane 1–butene functional group immediately in front of the ending
e) Topological or bar formula.- They show the of the name.
bond angle between carbon–carbon.
Examples:
c) Developed formula.- Expresses how the atoms CH – CH – CH = CH
that make up the molecule are linked together. Yo

HH
II CH 3
H –C = C –C –C –H
Yo III
h HHH Nomenclature 1979 Nomenclature 1993

1–butene
3-methyl-1-butene 3-methylbut-1-ene
d) Structural or spatial formula.- It uses spatial
molecular models that are used to build the CH 2 = CH–CH = CH 2
molecule, observe its spatial distribution, see the
geometry of the bonds, etc. This formula provides
the most realistic shape of the molecule. Nomenclature 1979 Nomenclature 1993

CH 3 –CH 2 –CH = CH 2

Nomenclature 1979 Nomenclature 1993

1–butene but–1–ene
- 10 - Nomenclature of Organic Chemistry

1,3-butadiene buta–1,3–diene
Systematic name trivial name
b) Trivial nomenclature.- Also called traditional or
common , rooted in conventional chemical
language, although it does not follow the ethene ethylene
predetermined rules. Many of these trivial names are
accepted by IUPAC.

Each discovered compound was usually given a HOOC – COOH

name that generally referred to its origin, such as, for
example, geraniol (present in geraniums), formic
acid (present in ants), lactic acid (present in milk), Systematic name trivial name
etc.

ethanedioic acid oxalic acid

CH2 = CH2

Types of carbon atoms in a chain.- Carbons can

be classified based on how many more carbons it is
attached to. There are four types of carbon atoms:

a) Primary carbon : A carbon is primary if it is

bonded only to one other carbon atom.

SPECIFIC HOLISTIC OBJECTIVE:................2

DIAMOND..............................................4
Hybrid state.............................................5
Carbon atom with sp 3 hybridization.......5
h...................................................................8
ox.................................................................8
H%CxH.......................................................8
OX...............................................................8
h...................................................................8
saturated chain.........................................9
CH 3 –CH 2 –CH = CH 2............................9
Nomenclature 1979 Nomenclature 19939
Nomenclature 1979 Nomenclature 19939
CH 2 = CH–CH = CH 2.............................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name.............10
Systematic name trivial name.............10
Isomers are differentiated by the order in which the atoms are bonded in the molecule. 21

Note : In this text we will mainly follow the

recommendations of 1979, complementing those of
1993, especially in the proposed exercises, it is
recommended to take them into account.
 Nomenclature of Organic Chemistry - 11 -

c) Isomerism of function : Different functional group . 21

Huacaya X1 drilling rig (Chuquisaca). .23
SELF APPRAISAL :.............................25
)..............................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:..............34
Characteristics of alkanes.- They are..35
Example:................................................35
Physical properties and uses of alkanes :35
3)............................................................38
4)............................................................38
5)............................................................47
6)............................................................47
8)............................................................47
2,3,6–trimethylheptane (SI)...................47
10)..........................................................47
11)..........................................................48
Radicals or complex substituents.- They are those substituents formed with primary and secondary
branches . To name them:.....................48
basic alkyl group ..................................48
3. HE name the branch followed secondary 48
Examples:..............................................48
12)..........................................................48
n–nonyl either nonyl............................49
Examples:..............................................49
isobutyl..................................................49
Examples:..............................................49
Examples:..............................................49
Examples:..............................................50
Examples:..............................................50
ter -pentil either....................................50
Incorrect: 3.4, 6,7,8...............................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:................................................51
Solved exercises on branched alkanes.- 51
5)............................................................52
Name:....................................................52
- 12 - Nomenclature of Organic Chemistry

4)............................................................52
2,3,5-trimethyl-4-propylheptane...........52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
1)............................................................54
2)............................................................54
3)............................................................54
4)............................................................54
5)............................................................54
6)............................................................54
8)............................................................60
9)............................................................60
10)..........................................................60
SELF APPRAISAL : ALKANES (II) 72
SPECIFIC HOLISTIC OBJECTIVE:..............84
Physical properties and uses of alkynes :85
In the common system , they are named as derivatives of acetylene . 85
Examples:..............................................85
Examples:..............................................85
Examples:..............................................86
2–pentine...............................................86
1–pentine...............................................86
1,3-butadiyne.........................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:..............................................87
Examples:..............................................87
Solved exercises on branched alkenes.- 87
5)............................................................88
6)............................................................88
PROPOSED EXERCISES....................91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write the
correct name:.........................................91
III. Write the semi-developed and topological formulas of the following alkenines: 91
4)............................................................93
5)............................................................93
6)............................................................93
ill...............................................................93
 Nomenclature of Organic Chemistry - 13 -

7)............................................................93
9)............................................................93
10)..........................................................93
12)..........................................................93
Yo..........................................................94
SELF APPRAISAL :.............................95
SPECIFIC HOLISTIC OBJECTIVE:..............98
POLLUTION DUE TO HYDROCARBONS98
1–cyclopropylbutane.............................99
Examples:..............................................99
Examples:..............................................99
Correct: 1, 1,3......................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I).......105
SELF APPRAISAL :...........................106
CYCLIC HYDROCARBONS (II)......106
5...........................................................106
wJCE...........................................................106
SPECIFIC HOLISTIC OBJECTIVE:............108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:............................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde.....................113
β-ethyl-γ-methyl -valeraldehyde.........113
Examples:............................................113
15)........................................................114
16)........................................................114
Aliphatic Aromatic Mixed................115
Examples:............................................115
Examples:............................................116
4-methyl-3-penten-2-one.....................116
Examples:............................................116
3-oxobutanal........................................116
2-oxobutanedial...................................116
YO. Write the formula of the following compounds: 117
- 14 - Nomenclature of Organic Chemistry

1)..........................................................117
1...........................................................118
6...........................................................118
2...........................................................118
3...........................................................118
4...........................................................118
9...........................................................118
F...........................................................118
10.........................................................118
SELF APPRAISAL :...........................120
3...........................................................120
4...........................................................120
5...........................................................120
6...........................................................120
8...........................................................120
9...........................................................120
10.........................................................120
1...........................................................121
CH— CH— CH— cO— CH— CH,. .121
7...........................................................121
2...........................................................121
3...........................................................121
4...........................................................121
5...........................................................121
8...........................................................121
9...........................................................121
10.........................................................121
CONTENT:....................................................122
SPECIFIC HOLISTIC OBJECTIVE:............123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group....................................124
Aliphatic Aromatics..........................124
CH 3 –CH= CH – COOH.......................125
2-butenoic acid....................................125
3-carboxyhexanedioic acid..................125
3-(1-carboxymethyl)hexaodioic acid. .125
Examples:............................................125
Nomenclature of Organic Chemistry - 15 -

2-methylbutenedioic acid....................126
Examples:............................................126
3-oxopentanoic acid............................126
Examples:............................................127
CH 2 – COOH..........................................137
Some important carboxylic acids.-......138
18)........................................................138
YO. Write the formula of the compounds:139
II. Write the name of the compounds:.139
1)..........................................................139
2)..........................................................139
3)..........................................................139
4)..........................................................139
5)..........................................................139
6)..........................................................139
7)..........................................................139
8)..........................................................139
9)..........................................................139
10)........................................................140
1)..........................................................141
6)..........................................................141
2)..........................................................141
3)..........................................................141
8...........................................................141
4)..........................................................141
5)..........................................................141
9)..........................................................141
10)........................................................141
1)..........................................................142
6)..........................................................142
2)..........................................................142
CH-CH-CH-COOH.............................142
7)..........................................................142
8)..........................................................142
4)..........................................................142
5)..........................................................142
9)..........................................................142
- 16 - Nomenclature of Organic Chemistry

10)........................................................142
SPECIFIC HOLISTIC OBJECTIVE:............144
USES OF ESTERS.....................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds 145
acid halide...........................................145
Ester.....................................................145
Anhydride............................................145
Amide..................................................145
Nitrile..................................................145
acid + alcohol......................................146
ester + water........................................146
The ester functional group is:..............146
R – COO –...........................................146
R – COO – R'......................................146
Salt.......................................................146
ethanoate ion (acetate)........................146
sodium ethanoate (sodium acetate).....146
Names..................................................146
Ester.....................................................146
Examples:............................................147
Examples:............................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate 147
Examples:............................................147
( R – COO)X.......................................148
Solved exercises on esters and salts :. .148
1)..........................................................148
2)..........................................................148
3)..........................................................148
4)..........................................................148
5)..........................................................148
6)..........................................................148
9)..........................................................153
Examples:............................................155
Examples:............................................155
1)..........................................................155
3)..........................................................155
4)..........................................................155
 Nomenclature of Organic Chemistry - 17 -

5)..........................................................155
1) Write the formula of the following compounds: 156
1)..........................................................158
6)..........................................................158
7)..........................................................158
either....................................................158
9)..........................................................158
5)..........................................................158
10)........................................................158
1)..........................................................159
6)..........................................................159
2)..........................................................159
3)..........................................................159
7)..........................................................159
8)..........................................................159
4)..........................................................159
5)..........................................................159
9)..........................................................159
10)........................................................159
SPECIFIC HOLISTIC OBJECTIVE:............162
SODIUM CYANIDE.................................162
Examples:............................................163
Aliphatic nitrile...................................163
Examples:............................................163
Examples:............................................163
Various exercises solved on nitriles.-..164
Examples:............................................164
cyclohexane carbonitrile.....................164
benzene carbonitrile............................164
Examples:............................................164
Examples:............................................164
R – NO 2.............................................166
Solved exercises on nitrocompounds.-166
PROPOSED EXERCISES..................167
1. Write the formulas for:.................167
5...........................................................168
1...........................................................168
- 18 - Nomenclature of Organic Chemistry

6...........................................................168
2...........................................................168
3...........................................................168
7...........................................................168
8...........................................................168
4...........................................................168
9...........................................................168
1...........................................................171
2...........................................................171
7...........................................................171
3...........................................................171
8...........................................................171
4...........................................................171
5...........................................................171
9...........................................................171
10.........................................................171
2...........................................................172
1...........................................................172
6...........................................................172
3...........................................................172
8...........................................................172
4...........................................................172
9...........................................................172
5...........................................................172
10.........................................................172
1...........................................................173
2...........................................................173
3...........................................................173
4...........................................................173
5...........................................................173
8...........................................................173
9...........................................................173
10.........................................................173
WEEBGRAPHY.................................178
b) Secondary carbon : A carbon is secondary if it
The two carbon atoms are primary is bonded to two carbon atoms.

h HH
Yo II
 Nomenclature of Organic Chemistry - 19 -

H –C –C –C –H The central carbon atom is secondary.

Yo II
h HH

Carbon chains.- There are different types of chains: - Heterocyclic: Some carbon atom in the cycle
was replaced by another atom, for example N, S,
a) Open or acyclic : The extreme carbon atoms are O, etc.
not bonded to each other; They do not form rings or
cycles. Could be: - Monocyclic: There is only one cycle.

- Linear: They do not have any type of substitution. - Polycyclic: There are several cycles united
Carbon atoms can be written in a straight line or c) Tertiary carbon : A carbon is tertiary if it is
bent to take up less space. bonded to three carbon atoms.

- Branched: From one of the carbons of the linear h HH

chain comes another or other secondary chains or Yo II
branches. H –C –C –C –H
Yo II
h CH 3 H
b) Closed or cyclic : The last carbon of the chain
joins the first, forming a cycle or ring. There are The central carbon atom is tertiary.
several types:

- Homocyclic: The atoms of the cycle are carbon d) Quaternary carbon : A carbon is quaternary if it
atoms. is bonded to four carbon atoms.

SPECIFIC HOLISTIC OBJECTIVE:.................2

DIAMOND..............................................4
Hybrid state..............................................5
Carbon atom with sp 3 hybridization........5
h...................................................................8
ox.................................................................8
H%CxH........................................................8
OX................................................................8
h...................................................................8
saturated chain..........................................9
CH 3 –CH 2 –CH = CH 2.............................9
Nomenclature 1979 Nomenclature 19939
Nomenclature 1979 Nomenclature 19939
CH 2 = CH–CH = CH 2..............................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name..............10
Systematic name trivial name..............10
Isomers are differentiated by the order in which the atoms are bonded in the molecule. 21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)...23
SELF APPRAISAL :.............................25
- 20 - Nomenclature of Organic Chemistry

)..............................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:...............34
Characteristics of alkanes.- They are. .35
Example:................................................35
Physical properties and uses of alkanes :35
3)............................................................38
4)............................................................38
5)............................................................47
6)............................................................47
8)............................................................47
2,3,6–trimethylheptane (SI)...................47
10)..........................................................47
11)..........................................................48
Radicals or complex substituents.- They are those substituents formed with primary and secondary
branches . To name them:......................48
basic alkyl group ...................................48
3. HE name the branch followed secondary 48
Examples:...............................................48
12)..........................................................48
n–nonyl either nonyl............................49
Examples:...............................................49
isobutyl...................................................49
Examples:...............................................49
Examples:...............................................49
Examples:...............................................50
Examples:...............................................50
ter -pentil either.....................................50
Incorrect: 3.4, 6,7,8................................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:................................................51
Solved exercises on branched alkanes.-.51
5)............................................................52
Name:.....................................................52
4)............................................................52
2,3,5-trimethyl-4-propylheptane............52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
 Nomenclature of Organic Chemistry - 21 -

1)............................................................54
2)............................................................54
3)............................................................54
4)............................................................54
5)............................................................54
6)............................................................54
8)............................................................60
9)............................................................60
10)..........................................................60
SELF APPRAISAL : ALKANES (II).72
SPECIFIC HOLISTIC OBJECTIVE:...............84
Physical properties and uses of alkynes :85
In the common system , they are named as derivatives of acetylene . 85
Examples:...............................................85
Examples:...............................................85
Examples:...............................................86
2–pentine................................................86
1–pentine................................................86
1,3-butadiyne..........................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:...............................................87
Examples:...............................................87
Solved exercises on branched alkenes.-.87
5)............................................................88
6)............................................................88
PROPOSED EXERCISES.....................91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write the
correct name:..........................................91
III. Write the semi-developed and topological formulas of the following alkenines: 91
4)............................................................93
5)............................................................93
6)............................................................93
ill................................................................93
7)............................................................93
9)............................................................93
10)..........................................................93
- 22 - Nomenclature of Organic Chemistry

12)..........................................................93
Yo...........................................................94
SELF APPRAISAL :.............................95
SPECIFIC HOLISTIC OBJECTIVE:...............98
POLLUTION DUE TO HYDROCARBONS98
1–cyclopropylbutane..............................99
Examples:...............................................99
Examples:...............................................99
Correct: 1, 1,3.......................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I)........105
SELF APPRAISAL :...........................106
CYCLIC HYDROCARBONS (II).......106
5............................................................106
wJCE...........................................................106
SPECIFIC HOLISTIC OBJECTIVE:.............108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:.............................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde......................113
β-ethyl-γ-methyl -valeraldehyde..........113
Examples:.............................................113
15)........................................................114
16)........................................................114
Aliphatic Aromatic Mixed.................115
Examples:.............................................115
Examples:.............................................116
4-methyl-3-penten-2-one.....................116
Examples:.............................................116
3-oxobutanal.........................................116
2-oxobutanedial....................................116
YO. Write the formula of the following compounds: 117
1)..........................................................117
1............................................................118
6............................................................118
 Nomenclature of Organic Chemistry - 23 -

2............................................................118
3............................................................118
4............................................................118
9............................................................118
F...........................................................118
10..........................................................118
SELF APPRAISAL :...........................120
3............................................................120
4............................................................120
5............................................................120
6............................................................120
8............................................................120
9............................................................120
10..........................................................120
1............................................................121
CH— CH— CH— cO— CH— CH,...121
7............................................................121
2............................................................121
3............................................................121
4............................................................121
5............................................................121
8............................................................121
9............................................................121
10..........................................................121
CONTENT:.....................................................122
SPECIFIC HOLISTIC OBJECTIVE:.............123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group....................................124
Aliphatic Aromatics..........................124
CH 3 –CH= CH – COOH........................125
2-butenoic acid.....................................125
3-carboxyhexanedioic acid..................125
3-(1-carboxymethyl)hexaodioic acid...125
Examples:.............................................125
2-methylbutenedioic acid.....................126
Examples:.............................................126
3-oxopentanoic acid.............................126
- 24 - Nomenclature of Organic Chemistry

Examples:.............................................127
CH 2 – COOH...........................................137
Some important carboxylic acids.-.......138
18)........................................................138
YO. Write the formula of the compounds:139
II. Write the name of the compounds:..139
1)..........................................................139
2)..........................................................139
3)..........................................................139
4)..........................................................139
5)..........................................................139
6)..........................................................139
7)..........................................................139
8)..........................................................139
9)..........................................................139
10)........................................................140
1)..........................................................141
6)..........................................................141
2)..........................................................141
3)..........................................................141
8............................................................141
4)..........................................................141
5)..........................................................141
9)..........................................................141
10)........................................................141
1)..........................................................142
6)..........................................................142
2)..........................................................142
CH-CH-CH-COOH..............................142
7)..........................................................142
8)..........................................................142
4)..........................................................142
5)..........................................................142
9)..........................................................142
10)........................................................142
SPECIFIC HOLISTIC OBJECTIVE:.............144
USES OF ESTERS......................................144
Nomenclature of Organic Chemistry - 25 -

Characteristics of carboxylic acid derivatives.- Esters They are compounds 145

acid halide............................................145
Ester.....................................................145
Anhydride.............................................145
Amide...................................................145
Nitrile...................................................145
acid + alcohol.......................................146
ester + water.........................................146
The ester functional group is:...............146
R – COO –............................................146
R – COO – R'.......................................146
Salt.......................................................146
ethanoate ion (acetate)........................146
sodium ethanoate (sodium acetate)......146
Names...................................................146
Ester.....................................................146
Examples:.............................................147
Examples:.............................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate 147
Examples:.............................................147
( R – COO)X........................................148
Solved exercises on esters and salts :...148
1)..........................................................148
2)..........................................................148
3)..........................................................148
4)..........................................................148
5)..........................................................148
6)..........................................................148
9)..........................................................153
Examples:.............................................155
Examples:.............................................155
1)..........................................................155
3)..........................................................155
4)..........................................................155
5)..........................................................155
1) Write the formula of the following compounds: 156
1)..........................................................158
- 26 - Nomenclature of Organic Chemistry

6)..........................................................158
7)..........................................................158
either.....................................................158
9)..........................................................158
5)..........................................................158
10)........................................................158
1)..........................................................159
6)..........................................................159
2)..........................................................159
3)..........................................................159
7)..........................................................159
8)..........................................................159
4)..........................................................159
5)..........................................................159
9)..........................................................159
10)........................................................159
SPECIFIC HOLISTIC OBJECTIVE:.............162
SODIUM CYANIDE..................................162
Examples:.............................................163
Aliphatic nitrile....................................163
Examples:.............................................163
Examples:.............................................163
Various exercises solved on nitriles.-. .164
Examples:.............................................164
cyclohexane carbonitrile......................164
benzene carbonitrile.............................164
Examples:.............................................164
Examples:.............................................164
R – NO 2..............................................166
Solved exercises on nitrocompounds.-.166
PROPOSED EXERCISES...................167
1. Write the formulas for:.................167
5............................................................168
1............................................................168
6............................................................168
2............................................................168
3............................................................168
 Nomenclature of Organic Chemistry - 27 -

7............................................................168
8............................................................168
4............................................................168
9............................................................168
1............................................................171
2............................................................171
7............................................................171
3............................................................171
8............................................................171
4............................................................171
5............................................................171
9............................................................171
10..........................................................171
2............................................................172
1............................................................172
6............................................................172
3............................................................172
8............................................................172
4............................................................172
9............................................................172
5............................................................172
10..........................................................172
1............................................................173
2............................................................173
3............................................................173
4............................................................173
5............................................................173
8............................................................173
9............................................................173
10..........................................................173
WEEBGRAPHY..................................178
Isomers.- Two or more different compounds that
have the same molecular formula (global), but
The central carbon atom is quaternary different structure , are called isomers .
Example:
- 28 - Nomenclature of Organic Chemistry

n-Butane and isobutane are isomers, therefore they Classification of organic compounds.- Each type of
are two different compounds. compound has a functional group that characterizes
it.
CH – CH – CH – CH CH – CH – CH
CH
CLASSIFICATION OF ORGANIC COMPOUNDS
butane methylpropane
(n- (isobutane) Functional
butane) Function name Example
group
Alkanes butane
Structural isomerism Cn H2n+2
(Paraffins)
Isomers are differentiated by the order in Alkenes propene
Cn H2n
(Olefins)

HYDROCARBONS
which the atoms are bonded in the molecule.
Alkynes tip
Cn H2n – 2
a) Chain isomerism : Different placement of (Acetylenes)
some atoms in the chain Cyclic cyclopentane
CnH2n
hydrocarbons

CH 3 –CH 2 –CH 2 –CH 3

Aromatic
© benzene
hydrocarbons
CH – CH – CH I CH 3
Halogenated
b) Position isomerism : R–X 1-chloropropane
Different position of derivatives
functional group.

Alcohols R–OH ethanol

CH 3 –CH 2 –CH 2 OH CH 3 – CH OH –
CH 3

c) Isomerism of function : Different functional

group . Phenols phenol
OXYGENATED COMPOUNDS

CH 3 – CH 2 OH CH 3 – O –CH 3
RO-R' methoxyethane
Ethers
Stereoisomerism „0
Rc" PH
Aldehydes propanal
Isomers are differentiated by the three-
dimensional arrangement of atoms in the 0
molecule. II
Ketones RCR propanone
a) Geometric or cis-trans isomerism : Typical of
compounds with double bonds . ,0
CH 3 CH 3 CH h R.C.
\/\/ Carboxylic acids OH propanoic acid
C=C C=C
h h h CH
Esters (and ,0
RCí, methyl acetate
cis–2–butene trans-2-butene salts)
B0-R
b) Optical isomerism : Typical of compounds with RNR" k
NITROGEN COMPOUNDS

asymmetric carbons , that is, with four different Amines ethylamine

substituents.
Ci
1
/$
H-2 or
ft

COOH COOH Amides propanamide

*1

OH ||r C C,,HO
4 PH H/k R-C=N
CH3 CH3 Nitriles propanenitrile

Nitrocompounds R-NO2 nitroethane

Nomenclature of Organic Chemistry - 29 -

Oil, natural source of hydrocarbons. - Oil has been more than 40 chemicals similar to kerogen, which is
known since prehistory. The Bible mentions it as supposed to be the precursor of oil, have been found in
bitumen or asphalt. several meteorites.

Petroleum is a Spanish word that comes from the The latest discoveries by NASA have proven that the
Latin petroleum (petra = stone and oleum = oil ). atmospheres of other planets have a high methane
content, it is not surprising that this theory is gaining
The inhabitants of Mesoamerica knew and used oil. On more followers every day.
some occasions, as waterproofing on their boats.
What is oil ? - It is a viscous liquid whose color varies
How was oil formed ? - There are several theories between yellow and dark brown to black, with green
about the formation of oil. However, the most accepted reflections. It also has a characteristic odor and floats
is the organic theory which assumes that it originated in water.
from the decomposition of the remains of animals and
microscopic algae accumulated at the bottom of It is necessary to deepen knowledge to determine not
lagoons and in the lower course of rivers. only its physical properties, but also the chemical
properties of its components.
This organic matter was gradually covered with
increasingly thicker layers of sediments, sheltered from Petroleum is a mixture of hydrocarbons ,
which, under certain conditions of pressure, compounds that contain mainly carbon and hydrogen in
temperature and time, it was slowly transformed into their molecular structure.
hydrocarbons (compounds formed of carbon and
hydrogen), with small amounts of sulfur. , oxygen, It contains, in a smaller proportion, other elements such
nitrogen, traces of metals such as iron, chromium, as O , S , N and even metals, such as Ni , Fe and V.
nickel and vanadium, the mixture of which constitutes
crude oil . The number of carbon atoms and the way they are
placed within the molecules of different compounds
These conclusions are based on the location of the oil provide oil with different physical and chemical
beds, since they are all located in sedimentary terrain. properties .
Furthermore, the compounds that form the
aforementioned elements are characteristic of living Name Use
No. carbon
organisms.
Natural gas C 1 to C 4 Fuel
There are other scholars who do not accept this theory,
their main argument consists of the inexplicable fact Petroleum ether C 5 to C 7 Solvent
that if it is true that there are more than 30,000 oil fields
in the entire world, until now only 33 of them constitute Gasoline C 5 to C 12
large deposits. Of those 25 are in the Middle East and Car fuel
contain more than 60% of our planet's proven reserves. Kerosene C 12 to C 16 Fuel
One wonders, then, how is it possible that so many
light oil C 15 to C 18 Diesel
animals have died in less than 1% of the Earth's crust,
which is the percentage that corresponds to the Middle
East? Lubricant oil C 16 to C 20 Lubrication

There are other theories that maintain that oil is of Paraffin C 20 to C 30 Candles
inorganic or mineral origin. Russian scientists are the
ones who have been most concerned with testing this Asphalt Greater than C 30 Pavement
hypothesis.
Residue Greater than C 30 Fuel
However, these proposals have not been accepted in
their entirety either.

An interesting version of this topic is the one published

by Thomas Gold in 1986. This European scientist says
that natural gas (methane), which is usually found in
large quantities in oil fields, could have been generated
from meteorites that fell during the formation of the
Earth millions of years ago.

The arguments he presents are based on the fact that

- 30 - Nomenclature of Organic Chemistry

Hydrocarbons composed of one to four carbon atoms it enters the distillation tower vaporized. Here, vapors
are gases, those containing 5 to 20 are liquid, and rise through floors or compartments that prevent the
those containing more than 20 are solid at room passage of liquids from one level to another. As the
temperature. vapors rise through the floors, they cool down. This
cooling causes different fractions to condense on each
The oil is “trapped” by geological formations. It of the floors, each of which has a specific liquefaction
occupies the pores of certain rocks in the deposits and temperature.
is subject to great pressure from the so-called “ natural
gas ”. The first vapors that liquefy are those of heavy diesel,
between 300°C and 370°C; then kerosene, between
When a well is drilled, pressure causes crude oil to flow 260°C and 350°C; then the fuel oil between 170°C and
through the pores and tubing of the well. 290°C; naphtha between 110°C and 195°C and finally,
gasoline and fuel gases between 30°C and 180°C that
leave the cooling tower still in the form of vapor.

This last fraction is sent to another distillation tower

where the gases are separated from the gasoline.

Light hydrocarbons
Gasoline

Gasoline

Kerosene

Gasoil

Lubricants
Huacaya X1 drilling rig (Chuquisaca)
Fuel Oil
atmospheric waste
Vacuum residue
The oil extracted from the subsoil has more value the
greater the amount of light hydrocarbons (between 5
and 12 carbons) it contains, since this is the fraction In this
from which gasoline is obtained. fractionation
tower,
Separation of oil into its fractions.- Crude oil varies distillation is
greatly in its composition; This depends on the type of carried out at
deposit from which it comes, but on average we can atmospheric
consider that it contains between 83 and 86% carbon pressure.
and between 11 and 13% hydrogen. Therefore, only
hydrocarbons
The higher the carbon content in relation to the containing 1 to
hydrogen content, the greater the amount of heavy 20 carbon
products in the crude oil. atoms can be
separated without decomposition.
The composition of crude oil also includes sulfur
derivatives (which smell like rotten eggs), in addition to Of the non-condensable gases, methane is the lightest
carbon and hydrogen. Some crude oils contain hydrocarbon, containing only one carbon atom and four
compounds of up to 30 to 40 carbon atoms. hydrogen atoms. Next is ethane , which is composed
of two carbon atoms and six hydrogen atoms.
How can oil be separated into its different fractions
? - A first distillation is carried out by heating, as the Methane is the main component of natural gas . It is
temperature rises, the compounds with fewer carbon sold as fuel in our country through household gas
atoms in their molecules (which are gaseous) are networks and now in transportation ( NGV ). This fuel
easily released; Afterwards, the liquid compounds are has significant amounts of ethane.
vaporized and also separated, and so on, the different
fractions are obtained. Liquefied petroleum gas ( LPG) is the fuel that is
distributed in cylinders (jerks) and stationary tanks for
In oil refineries, these separations are carried out in homes and buildings. This gas is made up of
cooling or primary distillation towers . To do this, hydrocarbons with 3 and 4 carbon atoms, called
the crude oil is first heated from 370°C to 400°C so that propane and butane .
Nomenclature of Organic Chemistry - 31 -

The next fraction is made up of virgin gasoline , which heptane and isooctane until the one that produces a
is made up of hydrocarbons with 4 to 9 carbon atoms. similar effect is found.
Most of these molecules have a linear structure.
For example, if a certain gasoline has knock
The fraction containing 10 to 14 carbon atoms has characteristics similar to those of a mixture of 90%
boiling temperatures of 260 °C to 350 °C, which isooctane and 10% normal heptane, then it is assigned
correspond to kerosene , from which the fuel for an octane rating of 90.
turbine aircraft, called jet fuel, is extracted.
What is petrochemistry ?- Petrochemistry includes
The last fraction to be distilled from the primary tower is the production of chemical products derived from
gas oil , which has a boiling range of 275°C to 400°C petroleum hydrocarbons and natural gas, with the
and contains 15 to 18 carbon atoms. From here the exception of fuel hydrocarbons, lubricants, waxes and
fuel called diesel is obtained, it is used for vehicles that asphalt.
use diesel engines such as tractors, locomotives,
trucks, trailers and ships. Petrochemicals are not considered to be a particular
type or class of chemicals, as many of them have been
It is clearly seen how almost the entire barrel of oil and continue to be manufactured from other raw
processed in refineries is used to manufacture fuel. materials.

The amount of virgin gasoline obtained depends on the For example, benzene, methanol and acetylene can be
type of crude oil (heavy or light), since in each case the produced from hard coal. Glycerol is obtained from
percentage of this fraction is variable. fats, ethanol from sugar cane fermentation, sulfur from
mineral deposits.
What does octane rating mean in gasoline ? - An
engine is designed so that first the gasified gasoline is However, all of them are also produced from oil and in
admitted to the piston and after being compressed, the large volumes.
spark from the spark plug causes the explosion.
Some chemicals are currently obtained almost entirely
Gasoline that explodes while being compressed is not from petroleum; a typical case is acetone, which was
suitable, that is, it burns prematurely (pre-ignition) as originally produced from the distillation of wood and,
this causes the piston to extend before the crankshaft later, from the fermentation of agricultural products.
has completed its cycle, which is heard as a knocking
noise called “ rattle”. , which destroys the engines. The development of modern chemistry after almost 50
years has shown that petroleum is the ideal raw
The tendency not to produce “rattle” is indicated by the material for the synthesis of most consumer chemicals.
octane rating (or octane rating) of each gasoline. In addition to its great abundance and availability, it is
made up of a great variety of compounds that present
50 years ago, it was discovered that of all the all possible carbonylated structures, which allows the
compounds that make up gasoline, normal heptane (a possibilities of new products to be increased even
hydrocarbon with seven carbon atoms in a linear further.
shape) is the one that causes the worst detonation. For
this reason, it was assigned a value of zero on the
corresponding scale.

The compound that detonated the least was the one

with eight carbon atoms, forming a branched chain
called isooctane . It was given a value of 100, and
thus the octane or octane ratings of gasoline were
born.

Octane Hydrocarbon Engine behavior

0 n-heptane Appalling

100 2,2,4-trimethylpentane Excellent

(isooctane)

How are gasoline octane ratings determined ? -

There are special devices to measure the detonations
they cause. The result is compared with mixtures of
- 32 - Nomenclature of Organic Chemistry

SELF APPRAISAL : ORGANIC CHEMISTRY a) An organic compound that dissolves in

(I water
1. It was the first organic compound prepared in a b) An organic compound that self-dissolves
laboratory. c) There is no such class of substances
d) An organic compound, usually liquid, that
a) Methyl Alcohol b) Methane Gas dissolves many other organic substances
c) Urea d) Benzene
10. Why do carbon compounds usually react so slowly?
2. Which of the following pairs of compounds are
made of pure carbon? a) Due to the strength of the ionic bond that unites
the atoms that form these substances
a) Graphite, basalt b) Diamond, graphite b) Because if the temperature increases they burn
c) Diamond, peat d) Graphite, lignite c) Because they are large molecules, shocks are
less effective
3. What energy is needed and what's it calledhe d) Due to the strength of the covalent bond that
process by which hedioxide carbon the unites the atoms that make up these substances
atmosphere is captured by plants?
11. Do carbon compounds conduct electricity?
a) Luminous, autotrophic
b) Luminous, photocomposition a) No, solids; yes, melted
c) Luminous, photosynthesis b) Both solid and molten
d) Luminous, heterotrophic c) Yes, solids; no, melted
d) Neither solid nor molten
4. Which of the following substances conducts electric
current? 12. It is a characteristic of inorganic compounds.

a) Limestone b) Basalt a) They are very volatile

c) Diamond d) Graphite b) They are not volatile
c) Their reactions require catalysts
5. Knowing that the carbon atom has an atomic d) His reactions are fast
number z = 6, what is its external electronic
configuration? 13. What is a molecular formula of an organic
compound?
a) 2s 2p 4 b) 2 s 2 p 2
c) 3s 2p 4 d) 1s 2p 4 a) Formula used to differentiate one substance
from another
6. How many covalent bonds does the carbon atom b) Formula that shows how exactly the atoms of
form when it joins other elements? the compound molecule are joined together
c) Formula that indicates the atoms that make up
a) Two b) One c) Four d) Three the molecule and the quantity in which they are
d) Formula that shows how the atoms of the
7. What is a carbon-carbon double bond? molecule are joined together, except hydrogen

a) Both carbon atoms share two pairs of electrons 14. Organic compounds dissolve in:
b) Double a single bond
c) Both atoms share six electrons a) Water b) Alcohol
d) Both atoms share a pair of electrons c) Organic solvents d) Acetylene

8. Which of the following properties is characteristic of

organic compounds?

a) Boiling temperatures are relatively high for most

of these substances.
b) They are all soluble in water
c) Great thermal stability
d) Melting temperatures are relatively low

9. What is an organic solvent?

Nomenclature of Organic Chemistry - 33 -

15. Organic compounds decompose at temperatures:

a) High b) Casualties
c) Very high d) Variable

16. It is the hardest substance known and only

covalent bonds occur in it:

a) Soot b)Graphite
c) Diamond d)Mineral carbon

17. It is an artificial charcoal:

a) Coal b)Lignite
c) Peat d)Lampblack

18. How many primary, secondary and tertiary

carbons exist in the following structure:

SPECIFIC HOLISTIC OBJECTIVE:...................2

DIAMOND.................................................4
Hybrid state.................................................5
Carbon atom with sp 3 hybridization..........5
h......................................................................8
ox....................................................................8
H%CxH..........................................................8
OX..................................................................8
h......................................................................8
saturated chain............................................9
CH 3 –CH 2 –CH = CH 2...............................9
Nomenclature 1979 Nomenclature 1993. 9
Nomenclature 1979 Nomenclature 1993. 9
CH 2 = CH–CH = CH 2.................................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name................10
Systematic name trivial name................10
Isomers are differentiated by the order in which the atoms are bonded in the molecule. 21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)......23
SELF APPRAISAL :................................25
).................................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:.................34
Characteristics of alkanes.- They are.....35
- 34 - Nomenclature of Organic Chemistry

Example:...................................................35
Physical properties and uses of alkanes :..35
3)...............................................................38
4)...............................................................38
5)...............................................................47
6)...............................................................47
8)...............................................................47
2,3,6–trimethylheptane (SI)......................47
10).............................................................47
11).............................................................48
Radicals or complex substituents.- They are those substituents formed with primary and secondary
branches . To name them:.........................48
basic alkyl group ......................................48
3. HE name the branch followed secondary 48
Examples:.................................................48
12).............................................................48
n–nonyl either nonyl...............................49
Examples:.................................................49
isobutyl.....................................................49
Examples:.................................................49
Examples:.................................................49
Examples:.................................................50
Examples:.................................................50
ter -pentil either.......................................50
Incorrect: 3.4, 6,7,8...................................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:...................................................51
Solved exercises on branched alkanes.-. . .51
5)...............................................................52
Name:........................................................52
4)...............................................................52
2,3,5-trimethyl-4-propylheptane...............52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
1)...............................................................54
2)...............................................................54
3)...............................................................54
4)...............................................................54
Nomenclature of Organic Chemistry - 35 -

5)...............................................................54
6)...............................................................54
8)...............................................................60
9)...............................................................60
10).............................................................60
SELF APPRAISAL : ALKANES (II)...72
SPECIFIC HOLISTIC OBJECTIVE:.................84
Physical properties and uses of alkynes :. 85
In the common system , they are named as derivatives of acetylene . 85
Examples:.................................................85
Examples:.................................................85
Examples:.................................................86
2–pentine..................................................86
1–pentine..................................................86
1,3-butadiyne............................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:.................................................87
Examples:.................................................87
Solved exercises on branched alkenes.-. . .87
5)...............................................................88
6)...............................................................88
PROPOSED EXERCISES.......................91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write the
correct name:............................................91
III. Write the semi-developed and topological formulas of the following alkenines: 91
4)...............................................................93
5)...............................................................93
6)...............................................................93
ill...................................................................93
7)...............................................................93
9)...............................................................93
10).............................................................93
12).............................................................93
Yo.............................................................94
SELF APPRAISAL :................................95
SPECIFIC HOLISTIC OBJECTIVE:.................98
- 36 - Nomenclature of Organic Chemistry

POLLUTION DUE TO HYDROCARBONS. 98

1–cyclopropylbutane................................99
Examples:.................................................99
Examples:.................................................99
Correct: 1, 1,3.........................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I)..........105
SELF APPRAISAL :..............................106
CYCLIC HYDROCARBONS (II).........106
5..............................................................106
wJCE..............................................................106
SPECIFIC HOLISTIC OBJECTIVE:...............108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:...............................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde........................113
β-ethyl-γ-methyl -valeraldehyde.............113
Examples:...............................................113
15)...........................................................114
16)...........................................................114
Aliphatic Aromatic Mixed...................115
Examples:...............................................115
Examples:...............................................116
4-methyl-3-penten-2-one........................116
Examples:...............................................116
3-oxobutanal...........................................116
2-oxobutanedial......................................116
YO. Write the formula of the following compounds: 117
1).............................................................117
1..............................................................118
6..............................................................118
2..............................................................118
3..............................................................118
4..............................................................118
9..............................................................118
Nomenclature of Organic Chemistry - 37 -

F..............................................................118
10............................................................118
SELF APPRAISAL :..............................120
3..............................................................120
4..............................................................120
5..............................................................120
6..............................................................120
8..............................................................120
9..............................................................120
10............................................................120
1..............................................................121
CH— CH— CH— cO— CH— CH,......121
7..............................................................121
2..............................................................121
3..............................................................121
4..............................................................121
5..............................................................121
8..............................................................121
9..............................................................121
10............................................................121
CONTENT:.......................................................122
SPECIFIC HOLISTIC OBJECTIVE:...............123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group.......................................124
Aliphatic Aromatics.............................124
CH 3 –CH= CH – COOH...........................125
2-butenoic acid.......................................125
3-carboxyhexanedioic acid.....................125
3-(1-carboxymethyl)hexaodioic acid......125
Examples:...............................................125
2-methylbutenedioic acid.......................126
Examples:...............................................126
3-oxopentanoic acid................................126
Examples:...............................................127
CH 2 – COOH..............................................137
Some important carboxylic acids.-.........138
18)...........................................................138
- 38 - Nomenclature of Organic Chemistry

YO. Write the formula of the compounds:139

II. Write the name of the compounds:....139
1).............................................................139
2).............................................................139
3).............................................................139
4).............................................................139
5).............................................................139
6).............................................................139
7).............................................................139
8).............................................................139
9).............................................................139
10)...........................................................140
1).............................................................141
6).............................................................141
2).............................................................141
3).............................................................141
8..............................................................141
4).............................................................141
5).............................................................141
9).............................................................141
10)...........................................................141
1).............................................................142
6).............................................................142
2).............................................................142
CH-CH-CH-COOH................................142
7).............................................................142
8).............................................................142
4).............................................................142
5).............................................................142
9).............................................................142
10)...........................................................142
SPECIFIC HOLISTIC OBJECTIVE:...............144
USES OF ESTERS........................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds 145
acid halide...............................................145
Ester........................................................145
Anhydride...............................................145
Nomenclature of Organic Chemistry - 39 -

Amide.....................................................145
Nitrile......................................................145
acid + alcohol..........................................146
ester + water............................................146
The ester functional group is:.................146
R – COO –..............................................146
R – COO – R'..........................................146
Salt..........................................................146
ethanoate ion (acetate)...........................146
sodium ethanoate (sodium acetate).........146
Names.....................................................146
Ester........................................................146
Examples:...............................................147
Examples:...............................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate147
Examples:...............................................147
( R – COO)X...........................................148
Solved exercises on esters and salts :.....148
1).............................................................148
2).............................................................148
3).............................................................148
4).............................................................148
5).............................................................148
6).............................................................148
9).............................................................153
Examples:...............................................155
Examples:...............................................155
1).............................................................155
3).............................................................155
4).............................................................155
5).............................................................155
1) Write the formula of the following compounds: 156
1).............................................................158
6).............................................................158
7).............................................................158
either.......................................................158
9).............................................................158
- 40 - Nomenclature of Organic Chemistry

5).............................................................158
10)...........................................................158
1).............................................................159
6).............................................................159
2).............................................................159
3).............................................................159
7).............................................................159
8).............................................................159
4).............................................................159
5).............................................................159
9).............................................................159
10)...........................................................159
SPECIFIC HOLISTIC OBJECTIVE:...............162
SODIUM CYANIDE.....................................162
Examples:...............................................163
Aliphatic nitrile.......................................163
Examples:...............................................163
Examples:...............................................163
Various exercises solved on nitriles.-.....164
Examples:...............................................164
cyclohexane carbonitrile.........................164
benzene carbonitrile................................164
Examples:...............................................164
Examples:...............................................164
R – NO 2.................................................166
Solved exercises on nitrocompounds.-...166
PROPOSED EXERCISES.....................167
1. Write the formulas for:....................167
5..............................................................168
1..............................................................168
6..............................................................168
2..............................................................168
3..............................................................168
7..............................................................168
8..............................................................168
4..............................................................168
9..............................................................168
Nomenclature of Organic Chemistry - 41 -

1..............................................................171
2..............................................................171
7..............................................................171
3..............................................................171
8..............................................................171
4..............................................................171
5..............................................................171
9..............................................................171
10............................................................171
2..............................................................172
1..............................................................172
6..............................................................172
3..............................................................172
8..............................................................172
4..............................................................172
9..............................................................172
5..............................................................172
10............................................................172
1..............................................................173
2..............................................................173
3..............................................................173
4..............................................................173
5..............................................................173
8..............................................................173
9..............................................................173
10............................................................173
WEEBGRAPHY....................................178
d) Fats and oils

a) 6;1;0 b) 5;2;2 c) 6;1,2 d) 2; 2; 2 21. The sp 2 type hybrid orbitals are oriented:

19. The two allotropic forms of carbon are: a) Towards the lower vertices of a hexahedron
b) Towards the vertices of a regular tetrahedron
a) Diamond and amorphous carbon c) Towards the vertices of an equilateral triangle
b) Graphite and amorphous carbon d) Towards the ends of a straight line forming 180º
c) Brown coal and peat
d) Diamond and graphite 22. Choose a pair of isomers

20. Organic chemistry studies:

a) Gases from oil

b) carbon compounds
c) Oil and its derivatives
- 42 - Nomenclature of Organic Chemistry

CH 3 - CO - CH 3
CH 3 - CH 2 - CH 3
CH - CH - CH = CH 2
CH 3 - CH 2 - CHO

SELF APPRAISAL : ORGANIC CHEMISTRY (II)

1. What is the area of knowledge that organic

chemistry covers?

a) The structure ofAny material

b) The minerals andtheirApplications
c) The compoundsof thecarbon
d) The compoundsof thesilicon

2. Which of the following properties characterizes

organic compounds?

a) High melting points

b) High solubility in water
c) They present ionic bond
d) They have a covalent bond

3. How is hybridization explained?

a) As a mixture of atoms
b) As a mixture of pure orbitals
c) As a mixture of p orbitals
d) As a mixture of molecular orbitals

4. Type of hybridization of carbon orbitals that

presents a single bond:

a) sp b) sp 2 c) sp 3 d) spd

5. Type of hybridization of carbon orbitals that

presents a double bond:

a) sp b) sp 2 c) sp 3 d) spd

6. Type of hybridization of carbon orbitals that

presents a triple bond:

CH 3 - CH 2 - CH OH
a) CH - CH 2 - COOH ;
CH 3 - CH = CH 2 ;
b) CH - CO - CH
3 3
c)
d)
Nomenclature of Organic Chemistry - 43 -

10. Which of the following combinations forms a skeleton exhibit?

sigma ( a ) bond between carbon atoms?
a) Chain isomerism
a) Two p orbitals b) Two sp 3 orbitals b) Functional isomerism
c) Three s orbitals d) Three p orbitals c) Position isomerism
d) geometric isomerism
11. When two pure p atomic orbitals overlap each
other, they form: 20. The Cis-trans geometric isomerism can be
presented in the hydrocarbons of cluster
a) A sigma ( a ) bond called:
b) A phi link (7)
c) Two sigma ( a ) bonds a) Alkanes b)Alkenes
d) Two sigma (T) bonds c) Saturated d) Aliphatic

12. The triple bond between carbon atoms is formed 21. What is the name of the formula that indicates only
by: the total number of atoms of each element that
participates in the compound?
a) Two sigma ( a ) and one phi (7) bonds
b) Three sigma ( a ) bonds a) Developed b) Synthetic
c) Two phi (7) and one sigma ( a ) bonds c) Semi-developed d) Condensed
d) Three phi links (7)
22. What type of formula is the following:
13. When there are four single bonds around a carbon
atom, it presents a hybridization: CH 3 – CH 2 – CH 2 – CH 2 – CH 3 ?

a) sp b) sp 2 c) sp 3 d) sp 4 a) Developed b) Synthetic
c) Semi-developed d) Condensed
14. The geometric structure of carbon atoms in
saturated hydrocarbons is: 23. For propane we have the following formula:

a) Square b) Flat HHH

c) Tetrahedral d) Linear | | |
H–C–C–C–H
15. The geometric distribution of the carbon orbitals, | | |
which have a double bond in a compound, is: HHH

a) Square b) Plane trigonal What type of formula does it correspond to?

c) Tetrahedral d) Linear
a) sp b) sp 2 c) sp 3 d) spd
16. What are saturated hydrocarbons known?
7. The orbitals sp 3 present a angle
a) Alkanes b) Alkenes approximated by each
c) Alkynes d) Aromatics other:

17. A hydrocarbon can be considered unsaturated a) 95° b) 109° c) 120° d) 180°

when it has: 8. The orbitals 2
sp present a angle
approximated by each
a) Simple links only other:
b) Linear chain only
c) Double links in the chain a) 95° b) 109° c) 120° d) 180°
d) Equal number of C and H atoms 9. The orbitals sp present a angle
approximated by each
18. What are compounds that have the same other:
molecular formula but have different properties
called? a) 95° b) 109° c) 120° d) 180°

a) Halogens b) Isomers a) Developed b) Synthetic

c) Olefins d) Isobars c) Semi-developed d) Condensed
19. What type of isomerism do atoms that differ in the
position of the functional group along the carbon
- 44 - Nomenclature of Organic Chemistry

24. What is the name of the atom or group of atoms

that is the reactive part of an organic molecule and
that they teach the majority of the
physical and chemical properties?

a) Functional group b) Reactive Group

c) Specific group d) Chemical group

25. What do all members of a class of compounds

have in common?

a) The same functional group

b) the same link
c) The number of carbons
d) The same type of hybridization
Nomenclature of Organic Chemistry - 45 -

Chap. 2

SATURATED HYDROCARBONS

ALKANES
- 46 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We value the influence of hydrocarbons on the economic

development of our country, through the study of the
properties and applications of alkanes, representing
compounds through formulas and naming them according
to systematic and trivial nomenclatures to apply in solving
problems in the process of comprehensive training of the
student.

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Gas and Oil Engineering is an engineering specialty that, based on the application of physical,
mathematical, chemical, mechanical, geological and economic concepts, is aimed at the
drilling of wells and the development of oil and gas fields; to its economic production; to the
separation and treatment of crude oil and natural gas; to the transportation of oil and natural gas
and finally to the conservation of hydrocarbons as non-renewable resources.

The Gas and Oil Engineer has his field of action in the different stages of the oil and natural gas
industry.

In our country they can develop their profession in the operating oil companies, national or foreign,
in the different specialized service companies that intervene in the industry, in the companies that
market petroleum derivatives such as fuels, lubricants, petrochemical products and in the
companies that provide equipment, advice and/or services and auditing companies.

The stages in which the Gas and Oil Engineer intervene are:

Exploration, Drilling, Production, Planning, Transportation, Storage, Marketing and

Negotiations of Petroleum Contracts and Audits and Refining Processes.

Study Gas and Oil Engineering at our San Francisco Xavier University to be a great
professional at the service of your country.
Nomenclature of Organic Chemistry - 47 -

Introduction.- Hydrocarbons are binary compounds

19 nonadec 20 eicos
whose molecules contain only carbon and hydrogen.
Characteristics of alkanes.- They are
Their importance is due to the fact that they are
Saturated chain hydrocarbons are so called because
currently the main source of carbon chains for the
they have only single bonds between carbon and
industry, they are the essential components of oil, coal
carbon.
and natural gas.

They are less dense than water and are also not
miscible with it. In the presence of oxygen they burn,
releasing a large amount of heat.

They are divided into two large groups:

• Acyclic, open-chain hydrocarbons , also called

aliphatic.

• Cyclic, closed-chain hydrocarbons , also called

alicyclics.

They are known as paraffins due to their low chemical

- Saturated ‘ Alkanes reactivity (from the Latin parum and affinis , little
HI ACYCLIC
reactivity ) .
d either
-
R ALIPHATIC - Not saturated Alkenes Alkanes comply with
EI • Alkynes the general formula:
cTH
TO ( Cycloalkanes
R CYCLIC - Alicyclics Cycloalkenes
b either Cycloalkynes C n H 2n+2
O CLOSED <
R - Aromatics Example: CH 3 – CH 2 – CH 2 –
EI either CH 3
Ye Benzene Butane ( C4H10 ) :
\

Classification of hydrocarbons Its structure presents carbon chains with sp 3

hybridization, the bonds are of the sigma ( a ) type
PREFIXES FOR IUPAC NOMENCLATURE between carbons and hydrogens.
C No. Prefix C No. Prefix
1 met 2 et

3 prop 4 but

5 pent 6 hex

7 hep 8 oct

9 no N 10 dec The simplest alkane is methane (CH 4 ), popularly

known as natural gas , since it is found in swampy
11 undec 12 dodec areas.

13 tridec 14 tetradec
Physical properties and uses of alkanes :
15 pentadec 16 hexadec
• The physical state of the first 4 alkanes: methane,
17 heptadec 18 octadec ethane, propane and butane is gaseous. From
pentane to hexadecane (16 carbon atoms) they are
- 48 - Nomenclature of Organic Chemistry
liquid and from heptadecane (17 carbon atoms) Examples:
they are solid. NAME SEMI-DEVELOPED TOPOLOGICAL
FORMULA FORMULA
• The melting point, boiling point and density increase
as the number of carbon atoms increases. CH 4
Methane
• They are insoluble in water.
CH 3 –CH 3
Ethane
• They can be used as solvents for less polar
substances such as fats, oils and waxes. CH 3 –CH 2 –CH 3
Propane
• Domestic gas for domestic use is methane. CH 3 –CH 2 –CH 2 –
Butane CH 3
• Bottled gas for domestic use is a mixture of alkanes,
CH 3 –(CH 2 ) 3 –CH 3
mainly propane. Pentane
• The gas in lighters is butane.
Hexane
CH 3 –(CH 2 ) 4 –CH 3 MUU

• Liquid hydrocarbons are used as fuels in the internal CH 3 –(CH 2 ) 5 –CH 3

K
combustion engines of automobiles, airplanes, etc. Heptane

• Gasoline is a mixture of octane to decane and the Octane

CH 3 –(CH 2 ) 6 –CH 3
paraffin from a candle, it is essentially triacontane
CH 3 –(CH 2 ) 7 –CH 3
Nonano
• The main use of alkanes is as fuels due to the large
amount of heat that is released in this reaction. CH 3 –(CH 2 ) 8 –CH 3
Example: Dean
CH 3 –(CH 2 ) 9 –CH 3
CH 4 + Or 2 ^ CO 2 + H 2 O + HEAT Undecan

• Methane is a fairly accessible hydrocarbon, which is

Linear or alkyl radicals.- Also called substituents,
increasingly used as a chemical raw material. The
reactions of its combustion and decomposition find they are alkane molecules that have lost a hydrogen
application in the production of carbon black atom due to a breakage of the covalent bond.
intended to obtain of the ink of
printing and rubber articles from rubber. Methane General Formula: –C n H 2n+1
too is a fountain
major of hydrogen production in the They are named by replacing the ending ano with il or
industry for the synthesis of ammonia and a series ilo .
of organic compounds.
Example:
• Its halogenation reaction allows obtaining –CH 3 –CH 2 – CH 3
halogenated derivatives of methane; which find
practical application as solvents, such as methyl– or methyl– ethyl– or ethyl–
dichloromethane and carbon tetrachloride. In
general, halogenated organic compounds are
toxic and many of them have been used in –CH 2 – CH 2 – CH 3 CH 3 – CH 2 – CH 2 – CH 2
agriculture as pesticides and insecticides, but their –
use has been restricted due to their high danger.
propyl– or propyl butyl– or butyl–
Nomenclature of alkanes.- To name alkanes there
are two systems, applying the rules of the IUPAC
(Systematic nomenclature) and the common or trivial
system.
Systematic nomenclature.- According to IUPAC
rules, the first four alkanes receive trivial names,
preserved by tradition: methane , ethane , propane ,
and butane . From the fifth onwards, the root of the
Greek number that indicates the number of carbon
atoms followed by the ending ano is used as a prefix.
Nomenclature of Organic Chemistry - 49 -

the one with the greatest number of substituents is

CH 3 – (CH 2 ) 3 – CH 2 – CH 3 – (CH 2 ) 4 – CH 2 – chosen.

Examples:
pentyl– or pentyl– hexyl– or hexyl–

The yl ending is preferred when considering the

isolated radical; The il ending is used when the radical
is attached to a carbon chain.

Branched alkanes.- In branched alkanes the following

components can be distinguished:
4. If the locator number is the same, the alphabetical
a) The main chain: It is the longest chain of carbons. order of the radicals is taken into account for the
numbering.
b) Primary branching: Short chain that arises from
the main chain (radicals or substituents that arise Example:
from the main chain)

c) Secondary branch: Shorter chain that arises from

a primary branch

3-ethyl-7-methylnonane
CH 3 –CH 2 –CH 2 –CH 2 –CH –CH 2 –CH 2 –CH 2 –CH 3
Yo
CH 2 5. Simple radicals are named in alphabetical order
Yo > Branching
‘2 0
8 E it 6 (the order of numbering is not taken into account),
EE secondary
("EM CH – CH 3 indicating their position.
or
Yo
6. The numbers indicating the position of the radicals
CH 3
are separated by commas and the numbers of the
radical names are separated by hyphens.

Nomenclature of branched alkanes.- The IUPAC

recommends taking into account the 1979 and 1993
standards.

1. The longest chain of carbons (main chain) is

chosen.

2. Number the main chain from the end closest to the

substituent (radical); in such a way that the lowest
numbers are assigned to the substituents (radicals).

Example
: First point of difference: 2

3. Correct: 2,3,4,5

Incorrect: 4,5,6,7

When there are two chains of

equal length that can be
selected as the main chain,
- 50 - Nomenclature of Organic Chemistry

3)
CH3-CH-CH2-CH2-CH3
CH-CH

3-methylhexane

4)
SPECIFIC HOLISTIC OBJECTIVE:............................2
DIAMOND.........................................................4
Hybrid state.........................................................5
7. When there are two or more identical substituents
on the main chain, multiplicative prefixes (di, tri, tetra, Carbon atom with sp 3 hybridization...................5
penta, etc.) are inserted before the name of the h..............................................................................8
substituent to indicate the number of those
substituents. Hyphens should not be used. ox............................................................................8
H%CxH...................................................................8
OX...........................................................................8
h..............................................................................8
saturated chain.....................................................9
CH 3 –CH 2 –CH = CH 2........................................9
Nomenclature 1979 Nomenclature 1993..........9
Nomenclature 1979 Nomenclature 1993..........9
CH 2 = CH–CH = CH 2.........................................10
Nomenclature 1979 Nomenclature 1993........10
Systematic name trivial name.........................10
Systematic name trivial name.........................10
Isomers are differentiated by the order in which
the atoms are bonded in the molecule...............21
c) Isomerism of function : Different functional
group ................................................................21
Huacaya X1 drilling rig (Chuquisaca)..............23
SELF APPRAISAL :........................................25
).........................................................................25
SELF APPRAISAL : ORGANIC
CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:..........................34
Characteristics of alkanes.- They are.............35
Example:...........................................................35
Physical properties and uses of alkanes :..........35
3).......................................................................38
4).......................................................................38
Nomenclature of Organic Chemistry - 51 -

5).......................................................................47
6).......................................................................47
8).......................................................................47
2,3,6–trimethylheptane (SI)..............................47
10).....................................................................47
11).....................................................................48
Radicals or complex substituents.- They are
those substituents formed with primary and
secondary branches . To name them:................48
basic alkyl group ..............................................48
3. HE name the branch followed secondary. .48
Examples:..........................................................48
12).....................................................................48
n–nonyl either nonyl.......................................49
Examples:..........................................................49
isobutyl..............................................................49
Examples:..........................................................49
Examples:..........................................................49
Examples:..........................................................50
Examples:..........................................................50
ter -pentil either................................................50
Incorrect: 3.4, 6,7,8...........................................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane
...........................................................................51
Example:...........................................................51
Solved exercises on branched alkanes.-............51
5).......................................................................52
Name:................................................................52
4).......................................................................52
2,3,5-trimethyl-4-propylheptane.......................52
YO. Write the semi-developed and topological
formulas of the following alkanes:....................54
1).......................................................................54
2).......................................................................54
3).......................................................................54
4).......................................................................54
5).......................................................................54
6).......................................................................54
- 52 - Nomenclature of Organic Chemistry

8).......................................................................60
9).......................................................................60
10).....................................................................60
SELF APPRAISAL : ALKANES (II)............72
SPECIFIC HOLISTIC OBJECTIVE:..........................84
Physical properties and uses of alkynes :..........85
In the common system , they are named as
derivatives of acetylene ....................................85
Examples:..........................................................85
Examples:..........................................................85
Examples:..........................................................86
2–pentine...........................................................86
1–pentine...........................................................86
1,3-butadiyne.....................................................86
Acetylenic radicals or substituents.- They are
incomplete molecules of an alkyne:..................87
Examples:..........................................................87
Examples:..........................................................87
Solved exercises on branched alkenes.-............87
5).......................................................................88
6).......................................................................88
PROPOSED EXERCISES................................91
YO. Write the semi-developed and topological
formulas of the following alkynes:...................91
II. There are errors in the following names of
alkynes, identify them, correct them and write
the correct name:...............................................91
III. Write the semi-developed and topological
formulas of the following alkenines:................91
4).......................................................................93
5).......................................................................93
6).......................................................................93
ill...........................................................................93
7).......................................................................93
9).......................................................................93
10).....................................................................93
12).....................................................................93
Yo......................................................................94
Nomenclature of Organic Chemistry - 53 -

SELF APPRAISAL :........................................95

SPECIFIC HOLISTIC OBJECTIVE:..........................98
POLLUTION DUE TO HYDROCARBONS..........98
1–cyclopropylbutane.........................................99
Examples:..........................................................99
Examples:..........................................................99
Correct: 1, 1,3..................................................100
YO. Write the formula corresponding to the
following cycloalkanes:..................................103
CYCLIC HYDROCARBONS (I)...................105
SELF APPRAISAL :......................................106
CYCLIC HYDROCARBONS (II)..................106
5.......................................................................106
wJCE......................................................................106
SPECIFIC HOLISTIC OBJECTIVE:........................108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT
................................................................................108
Physical properties of aldehydes and ketones :
.........................................................................109
Examples:........................................................113
Common nomenclature.- Aldehydes are named
in three ways :.................................................113
1. With their empirical names derived from the
corresponding carboxylic acids.......................113
α-methyl- butyraldehyde.................................113
β-ethyl-γ-methyl -valeraldehyde.....................113
Examples:........................................................113
15)...................................................................114
16)...................................................................114
Aliphatic Aromatic Mixed............................115
Examples:........................................................115
Examples:........................................................116
4-methyl-3-penten-2-one................................116
Examples:........................................................116
3-oxobutanal....................................................116
2-oxobutanedial...............................................116
YO. Write the formula of the following
compounds:.....................................................117
- 54 - Nomenclature of Organic Chemistry

1).....................................................................117
1.......................................................................118
6.......................................................................118
2.......................................................................118
3.......................................................................118
4.......................................................................118
9.......................................................................118
F......................................................................118
10.....................................................................118
SELF APPRAISAL :......................................120
3.......................................................................120
4.......................................................................120
5.......................................................................120
6.......................................................................120
8.......................................................................120
9.......................................................................120
10.....................................................................120
1.......................................................................121
CH— CH— CH— cO— CH— CH,..............121
7.......................................................................121
2.......................................................................121
3.......................................................................121
4.......................................................................121
5.......................................................................121
8.......................................................................121
9.......................................................................121
10.....................................................................121
CONTENT:................................................................122
SPECIFIC HOLISTIC OBJECTIVE:........................123
HOW TO REDUCE URIC ACID WITH NATURAL
REMEDIES............................................................123
Carboxyl group...............................................124
Aliphatic Aromatics.....................................124
CH 3 –CH= CH – COOH...................................125
2-butenoic acid................................................125
3-carboxyhexanedioic acid.............................125
3-(1-carboxymethyl)hexaodioic acid..............125
Nomenclature of Organic Chemistry - 55 -

Examples:........................................................125
2-methylbutenedioic acid................................126
Examples:........................................................126
3-oxopentanoic acid........................................126
Examples:........................................................127
CH 2 – COOH......................................................137
Some important carboxylic acids.-..................138
18)...................................................................138
YO. Write the formula of the compounds:.....139
II. Write the name of the compounds:.............139
1).....................................................................139
2).....................................................................139
3).....................................................................139
4).....................................................................139
5).....................................................................139
6).....................................................................139
7).....................................................................139
8).....................................................................139
9).....................................................................139
10)...................................................................140
1).....................................................................141
6).....................................................................141
2).....................................................................141
3).....................................................................141
8.......................................................................141
4).....................................................................141
5).....................................................................141
9).....................................................................141
10)...................................................................141
1).....................................................................142
6).....................................................................142
2).....................................................................142
CH-CH-CH-COOH.........................................142
7).....................................................................142
8).....................................................................142
4).....................................................................142
5).....................................................................142
- 56 - Nomenclature of Organic Chemistry

9).....................................................................142
10)...................................................................142
SPECIFIC HOLISTIC OBJECTIVE:........................144
USES OF ESTERS.................................................144
Characteristics of carboxylic acid derivatives.-
Esters...................................... They are compounds
145
acid halide.......................................................145
Ester................................................................145
Anhydride........................................................145
Amide..............................................................145
Nitrile..............................................................145
acid + alcohol..................................................146
ester + water....................................................146
The ester functional group is:..........................146
R – COO –.......................................................146
R – COO – R'..................................................146
Salt..................................................................146
ethanoate ion (acetate)...................................146
sodium ethanoate (sodium acetate).................146
Names..............................................................146
Ester................................................................146
Examples:........................................................147
Examples:........................................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate....147
Examples:........................................................147
( R – COO)X...................................................148
Solved exercises on esters and salts :..............148
1).....................................................................148
2).....................................................................148
3).....................................................................148
4).....................................................................148
5).....................................................................148
6).....................................................................148
9).....................................................................153
Examples:........................................................155
Examples:........................................................155
Nomenclature of Organic Chemistry - 57 -

1).....................................................................155
3).....................................................................155
4).....................................................................155
5).....................................................................155
1) Write the formula of the following
compounds:.....................................................156
1).....................................................................158
6).....................................................................158
7).....................................................................158
either................................................................158
9).....................................................................158
5).....................................................................158
10)...................................................................158
1).....................................................................159
6).....................................................................159
2).....................................................................159
3).....................................................................159
7).....................................................................159
8).....................................................................159
4).....................................................................159
5).....................................................................159
9).....................................................................159
10)...................................................................159
SPECIFIC HOLISTIC OBJECTIVE:........................162
SODIUM CYANIDE.............................................162
Examples:........................................................163
Aliphatic nitrile...............................................163
Examples:........................................................163
Examples:........................................................163
Various exercises solved on nitriles.-.............164
Examples:........................................................164
cyclohexane carbonitrile.................................164
benzene carbonitrile........................................164
Examples:........................................................164
Examples:........................................................164
R – NO 2.........................................................166
Solved exercises on nitrocompounds.-............166
- 58 - Nomenclature of Organic Chemistry

PROPOSED EXERCISES..............................167
1. Write the formulas for:............................167
5.......................................................................168
1.......................................................................168
6.......................................................................168
2.......................................................................168
3.......................................................................168
7.......................................................................168
8.......................................................................168
4.......................................................................168
9.......................................................................168
1.......................................................................171
2.......................................................................171
7.......................................................................171
3.......................................................................171
8.......................................................................171
4.......................................................................171
5.......................................................................171
9.......................................................................171
10.....................................................................171
2.......................................................................172
1.......................................................................172
6.......................................................................172
3.......................................................................172
8.......................................................................172
4.......................................................................172
9.......................................................................172
5.......................................................................172
10.....................................................................172
1.......................................................................173
2.......................................................................173
3.......................................................................173
4.......................................................................173
5.......................................................................173
8.......................................................................173
9.......................................................................173
10.....................................................................173
 Nomenclature of Organic Chemistry - 59 -

WEEBGRAPHY.............................................178

Yo
CH 3

4-ethyl-2-methylhexane
Correct: 2,2– CH 3 –CH 2 –C –CH 2
Example dimethylpentane –CH 2 –CH 3
:
Yo
Incorrect: 2–
dimethylpentan CH 2
e Yo
5) CH 3
CH 3
3-ethyl-3-methylhexane
Yo
Solved exercises.- C
Analyze and solve the H
following examples again: 2
-
1) C
6 5 4 3 21
H
2
CH 3 –CH 2 –CH 2 –CH 2 –CH –CH -
CH 3 C
H
2-methylhexane 3
CH - CH- CH - CH - CH -
2) CH 2 - CH - CH 3
CH 3 I CH, CH 2 - CH
CH 3 –C –CH 2 –CH –CH 3 II
CH CH
4-ethyl-2-methyl-5-
propyloctane
2,2,4–trimethylpentane
8)
C
H

6) C
H
C2H5
3
Yo
Yo
CH 3 –CH –CH –CH –CH 3 CH 3 –CH 2 –CH –
Yo Yo CH –CH 2 –CH 3
CH 3 C2H5 Yo
CH 3
3-ethyl-2,4-dimethylhexane
4-ethyl-3-
7)
- 60 - Nomenclature of Organic Chemistry

methyl hexane Main chain: The longest

(NO) (10 carbons), ten .
3-ethyl-4-
methyl
Numeration: It is
hexane (SI)
numbered starting with
9)
CH 3 –CH –CH
2 right, so that the
1 –CH2 –CH –CH –CH3 1
substituents take the minor
Yo II locators 3,4,5,8
CH 3 CH 3 CH 3

2,3,6–
Substituents: Methyls in
trimethylhept
positions 4,8 and ethyls in
ane (SI)
positions 3,5.

2,5,6–
trimethylhexa Name: 3,5 –di ethyl – 4,8 –
ne (NO) di methyl decane

10)
Radicals or complex
substituents.- They are
those substituents
formed with primary and
secondary branches . To
name them:
Main chain:
1. HE identifies the
The longest longest branch as
(5 carbons), pentane . basic alkyl group .

Numeration: Start on the 2. HE list again,

left to starting in it
give the lowest locator to carbon that has the free
methyl . bond.

Substituents: Methyl in 3. HE name the branch

position 2 followed secondary
of the primary branching
Name: 2 – methyl pentane , all within
parenthesis
11)
Examples:

CH 3 CH 3
I2 3I 4
–C –CH –CH–CH
Yo
CH 3

(1,1,3 – trimethylbutyl)

Main chain: The longest (6 carbons),

hexane .
Nomenclature of Organic Chemistry - 61 -

Numbering: You can start

at any of the ends given the
symmetry of the molecule.

Substituents: Methyls in
position 3,4

Name: 3,4 –dimethyl

hexane

12)

1I 2 3

CH 3 –CH 2 –CH–CH –CH 3

Yo

CH 3

(1-ethyl-2-methylpropyl)

Common or trivial
nomenclature of alkanes.-
It is an old nomenclature,
there is no rule to name
compounds. Generally the
name is due to its origin or
some property of the
substance.

1. When the carbons are

found in a continuous
chain, the word “ normal ”
or the prefix “ n ” is used
before naming the family.
- 62 - Nomenclature of Organic Chemistry

Examples: CH 3 – (CH 2 ) 7 – CH 2 –

CH 3 – (CH 2 ) 5 – CH 3 CH 3 – (CH 2 ) n–nonyl

either
n–heptane n–nonano nonyl

2. In the case of branched 2. “iso” radicals.- When

chains, the ISO prefix is there is a –CH 3 group
used when there is a –CH 3 attached to the
group attached to the penultimate carbon atom
penultimate carbon atom of the primary branch,
hydrogen is extracted from
the first carbon of the chain.

Examples
:

CH 3 – CH 2 – CH 2
–

n-propyl
either
propyl

of the main chain.

3. In the case of branched
chains, the prefix MESO is
used when there are two –
CH 3 groups attached to the
second and penultimate
carbon atoms of the main
chain.

CH 3 CH 3
Yo Yo
CH – C – CH – CH CH 3 –C – (CH 2
Yo Yo
CH 3 CH 3

neohexane neoheptane

Common nomenclature
of radicals.- Common
names are used as a base,
adding the prefixes: n,
ISO , NEO , SEC and TER.

1. Radicals “n” .- For

normal chains
Nomenclature of Organic Chemistry - 63 -

Examples:
32 1
CH – CH – I CH 3 –CH –CH 2 –
CH 3 Yo
CH 3
isopropyl
either isobutyl
(1 –
either
methylethyl)
(2 – methylpropyl)

3. “Neo” radicals.- When there are two –CH 3 groups

attached to the penultimate atom of the primary branch.

Examples:
4. In the case of
branched chains, the prefix
NEO is used when there
are two –CH 3 groups
attached to the
penultimate carbon atom
of the main chain.

Examples:
CH 3
4 3I 2 1
CH 3 –C –CH 2 –CH 2 –
Yo
CH 3

neohexyl or (3,3 –
dimethylbutyl)
- 64 - Nomenclature of Organic Chemistry

recommendations of the
CH 3 IUPAC
Yo
CH 3 –C –(CH 2 ) 2 –CH 2 – 1. When carrying out
Yo alphabetical order,
CH 3 numerical prefixes such
as di , tri , tetra, as well as
the letters that indicate the
neoheptyl or (4,4 – type of structure are not
dimethylpentyl) taken into account: sec- ,
ter- , ortho , meta , para ,
cis , trans .
4. “sec–” radicals.-
On the contrary, the
When an H atom is
prefixes are considered
extracted from the
alphabetically: cycle , iso ,
secondary carbon (
meso and neo.
second of the normal
chain ).
For example: a methyl ,
will be in a name before a
Examples:
dipropyl , but after an
isopropyl .
Yo
CH 3 –CH –CH 2 –CH 3 Example:
sec -butyl
either
(1 – methylpropyl)

CH 3 –CH –CH
2 –CH 2
–CH 3 I
sec -pentil
either
(1 – methylbutyl)

5. “ter–” radicals.- When

Yo an H atom is extracted
CH 3 –C –CH 3 from a tertiary carbon of
Yo the main chain.
CH 3
Examples: In the following example,
the two numbering senses
tert -butyl produce the indices
Yo
either 3,4,5,7,8 and 3,4,6,7,8.
CH 3 –C –CH 2 –CH 3
(1,1 –
Yo
CH 3 Since the first number of
each numbering sequence
is identical (3), we compare
ter -pentil the second index and
either observe that they are also
(1,1 – equal (4).
dimethylpropyl)

Nomenclature of alkanes
with complex radicals.-
Continuing the
Nomenclature of Organic Chemistry - 65 -

When comparing the third

index it is observed that
they are different (5 and 6).
This is the first point of
difference and the
sequence with the lowest
index is chosen (5).

Correct: 3,4, 5,7,8

- 66 - Nomenclature of Organic Chemistry

Incorrect: 3.4, 6,7,8 made up of identical words,

priority will be given to
the radical that has the
Name: 8-ethyl-4- lowest locator at the first
isopropyl-3,5,7- point of difference.
trimethyldecane

To name alkanes with

complex radicals, change
the way you name them, as
follows:

2. Complex radicals are

ordered according to their 6 –(1-methylbutyl)– 7 –(2-
first letter (taking into methylbutyl)dodecane
account the numeral
prefixes), that is, in this
case the multiplicative 3. When there are
prefixes di , tri , tetra , etc., repeated complex radicals,
are considered as part of they are named with
the name of the radical. multiplicative group
prefixes, such as those that
For simple radicals, it is will be used in inorganic
true: ethyl comes before nomenclature. (bis = 2; tris
dimethyl and this comes = 3; tetrakis = 4; etc.)
before propyl . Yo
If the complex radicals are:
CH – CH 3
I
(1,1- dimethylethyl ), CH 3

ethyl and methyl .

Example:
The order will be: The d
CH 3 –CH 2 –CH –CH 2 –
before the e . CH –CH 2 –CH 2 –CH 3
Yo
To alphabetize the names CH 3 – CH
of complex radicals that are Yo
CH 3
3,5-bis-(1-methylethyl)octane

Solved exercises on branched alkanes.-

Analyze and re-solve the following examples:

1)
Nomenclature of Organic Chemistry - 67 -

Main chain: 10 carbons ( decane ).

Numbering: Starting from the left, to give the substituents

the smallest locators.
Substituents: Methyls at 2,9 ; ethyl in 3 ; propyl in 7 ; 1-
methylpropyl in 4 .
N
a
m
e
:

e
t
h
y
l
–

2
,
9

–
d
i
m
e
t
h
y
l
–

–
(

1
-
m
e
t
h
y
l
p
r
o
p
y
l
)
- 68 - Nomenclature of Organic Chemistry

–
propyl dean
Nomenclature of Organic Chemistry - 69 -

2) 5)

CH 3
1 2 I 3 4 5 6

CH 3 – CH – CH – CH 2 – CH 2 – CH 3
Yo
1
CH – CH 3
Yo
2
CH 3

Main chain: (10 carbons), decane . 6)

Substituents: Methyls in positions 2,8 ; propyls in

4,7 and 2-methylpropyl in 6 .

5-(2-ethylbutyl)-3,3-

No: 5-(2,2-dimethylbutyl)-3-

7)

Name: 2,8 –dimethyl – 6 –( 2-methylpropyl ) – 6-ethyl-3,3-

4,7 –
di propyl dean
3-(1-methylethyl)-2-methylhexane
Main chain: (11 carbons), undecane .

Numbering: Starts on the left. No: 3-ethyl-6,6-dimethyl octane

4)
Substituents: Methyls in position 3,4 ,
CH 3 – CH 2 – CH – CH – CH – CH – CH 3 IIII Alkyl halides.- In the common nomenclature of
ethyls in 4,5 , isopropyl in 5 and propyl CH 3 CH 2 CH these
3 CH 3
compounds, their names are similar to those of
in 6 . inorganic salts.
N Yo
a CH 2
m –diethyl – 3,4 –dimethyl – 5 –
4,5 Yo
e
isopropyl CH 3undecane
–6– propyl
:

butyl isopropyl
chloride bromide
Each halogen atom is named with the prefixes
fluorine, chlorine, bromine, and iodine and is treated
as if it were another alkyl substituent.

Examples
:
2,3,5-trimethyl-4-
- 70 - Nomenclature of Organic Chemistry
 Nomenclature of Organic Chemistry - 71 -

PROPOSED EXERCISES
YO. Write the semi-developed and topological II. Write the name of the following formulas:
formulas of the following alkanes:
1)
1) 4-isopropylheptane CH –CH–CH –CH
Yo Yo
2) 3-ethyl-2-methylpentane CH CH

3) 5– ter -butyl–4–isopropylnonane
2)
4) 5-(2-methylpropyl)-nonane CH –CH–CH –CH –CH I
CH
5) 3-ethyl-2,5-dimethylheptane

6) 4-isopropyl-7,7-dimethyldecane 3)

7) 4-isopropyl-2,4,5-trimethylheptane CH
Yo
8) 4-ethyl-3-isopropyl-2,6-dimethyloctane CH – C – CH
Yo
9) 3-ethyl-5-isobutyl-3-isopropyl-6-methyloctane CH

10) 5- tert -butyl-3-ethyl-2,3-dimethyloctane 4)

11) 4-ethyl-3,5-dimethylheptane CH – CH – CH – CH – CH I
CH
12) 8-ethyl-4-isopropyl-3,5,7-trimethyldecane Yo
CH
13) 5-ethyl-3,3-dimethyl-7-propyldecane

14) 6-isopropyl-2,5-dimethylnonane 5)
CH – CH
15) 4-tert-butyl-3-methylheptane Yo
CH –CH–CH –CH –CH–CH I Yo
16) 5,5-diethyl-2-methyl-4-propyldecane
CH CH
17) 4,5-diethyl-5-isopropyl-3,4-dimethyl-6- I CH
propilundecane I CH

18) 5-(1,2-dimethylpropyl)-3,7-diethylundecane 6)
19) 5-(2-ethylbutyl)-3,4-dimethyldecane CH CH – CH

20) 6-ethyl-2,2,3-trimethyl-4-propylnonane

21) 4-ethyl-3-methyl-5,7-dipropyldecane

22) 5-(2,2,-dimethylpropyl)-4-propylnonane

23) 4-(1,1-dimethylethyl)-2-methyloctane

24) 4,8,10-trimethyl-7-(1,2,3-
trimethylpentyl)tetradecane

25) 5-sec-butyl-6-ethyl-7-isopropyl-4,4-dimethyl-6-
propyldecane

26) 3,6,7-trimethyl-9-(1,3,4-trimethylhexyl)-10-
(1,2,3-trimethylhexyl)heptadecane
- 72 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:...........2

DIAMOND........................................4
Hybrid state........................................5
Carbon atom with sp 3 hybridization..5
h.............................................................8
ox...........................................................8
H%CxH..................................................8
OX..........................................................8
h.............................................................8
saturated chain....................................9
CH 3 –CH 2 –CH = CH 2.......................9
Nomenclature 1979 Nomenclature 1993 9
Nomenclature 1979 Nomenclature 1993 9
CH 2 = CH–CH = CH 2........................10
Nomenclature 1979 Nomenclature 1993 10
Systematic name trivial name........10
Systematic name trivial name........10
Isomers are differentiated by the order in which the atoms are bonded in the molecule.
..........................................................21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)23
SELF APPRAISAL :........................25
)........................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:.........34
Characteristics of alkanes.- They are35
Example:..........................................35
Physical properties and uses of alkanes : 35
3)......................................................38
4)......................................................38
5)......................................................47
6)......................................................47
8)......................................................47
2,3,6–trimethylheptane (SI).............47
10)....................................................47
11)....................................................48
 Nomenclature of Organic Chemistry - 73 -

Radicals or complex substituents.- They are those substituents formed with primary and
secondary branches . To name them:48
basic alkyl group .............................48
3. HE name the branch followed secondary 48
Examples:.........................................48
12)....................................................48
n–nonyl either nonyl......................49
Examples:.........................................49
isobutyl.............................................49
Examples:.........................................49
Examples:.........................................49
Examples:.........................................50
Examples:.........................................50
ter -pentil either...............................50
Incorrect: 3.4, 6,7,8..........................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:..........................................51
Solved exercises on branched alkanes.- 51
5)......................................................52
Name:...............................................52
4)......................................................52
2,3,5-trimethyl-4-propylheptane......52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
1)......................................................54
2)......................................................54
3)......................................................54
4)......................................................54
5)......................................................54
6)......................................................54
8)......................................................60
9)......................................................60
10)....................................................60
SELF APPRAISAL : ALKANES (II) 72
SPECIFIC HOLISTIC OBJECTIVE:.........84
Physical properties and uses of alkynes : 85
In the common system , they are named as derivatives of acetylene . 85
- 74 - Nomenclature of Organic Chemistry

Examples:.........................................85
Examples:.........................................85
Examples:.........................................86
2–pentine..........................................86
1–pentine..........................................86
1,3-butadiyne....................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:.........................................87
Examples:.........................................87
Solved exercises on branched alkenes.- 87
5)......................................................88
6)......................................................88
PROPOSED EXERCISES...............91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write
the correct name:..............................91
III. Write the semi-developed and topological formulas of the following alkenines:
91
4)......................................................93
5)......................................................93
6)......................................................93
ill..........................................................93
7)......................................................93
9)......................................................93
10)....................................................93
12)....................................................93
Yo.....................................................94
SELF APPRAISAL :........................95
SPECIFIC HOLISTIC OBJECTIVE:.........98
POLLUTION DUE TO HYDROCARBONS 98
1–cyclopropylbutane........................99
Examples:.........................................99
Examples:.........................................99
Correct: 1, 1,3.................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I). .105
SELF APPRAISAL :......................106
 Nomenclature of Organic Chemistry - 75 -

CYCLIC HYDROCARBONS (II).106

5......................................................106
wJCE......................................................106
SPECIFIC HOLISTIC OBJECTIVE:.......108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:.......................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde................113
β-ethyl-γ-methyl -valeraldehyde....113
Examples:.......................................113
15)..................................................114
16)..................................................114
Aliphatic Aromatic Mixed...........115
Examples:.......................................115
Examples:.......................................116
4-methyl-3-penten-2-one................116
Examples:.......................................116
3-oxobutanal...................................116
2-oxobutanedial..............................116
YO. Write the formula of the following compounds: 117
1)....................................................117
1......................................................118
6......................................................118
2......................................................118
3......................................................118
4......................................................118
9......................................................118
F......................................................118
10....................................................118
SELF APPRAISAL :......................120
3......................................................120
4......................................................120
5......................................................120
6......................................................120
- 76 - Nomenclature of Organic Chemistry

8......................................................120
9......................................................120
10....................................................120
1......................................................121
CH— CH— CH— cO— CH— CH,121
7......................................................121
2......................................................121
3......................................................121
4......................................................121
5......................................................121
8......................................................121
9......................................................121
10....................................................121
CONTENT:...............................................122
SPECIFIC HOLISTIC OBJECTIVE:.......123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group...............................124
Aliphatic Aromatics.....................124
CH 3 –CH= CH – COOH..................125
2-butenoic acid...............................125
3-carboxyhexanedioic acid.............125
3-(1-carboxymethyl)hexaodioic acid125
Examples:.......................................125
2-methylbutenedioic acid...............126
Examples:.......................................126
3-oxopentanoic acid.......................126
Examples:.......................................127
CH 2 – COOH.....................................137
Some important carboxylic acids.-.138
18)..................................................138
YO. Write the formula of the compounds: 139
II. Write the name of the compounds:139
1)....................................................139
2)....................................................139
3)....................................................139
4)....................................................139
 Nomenclature of Organic Chemistry - 77 -

5)....................................................139
6)....................................................139
7)....................................................139
8)....................................................139
9)....................................................139
10)..................................................140
1)....................................................141
6)....................................................141
2)....................................................141
3)....................................................141
8......................................................141
4)....................................................141
5)....................................................141
9)....................................................141
10)..................................................141
1)....................................................142
6)....................................................142
2)....................................................142
CH-CH-CH-COOH........................142
7)....................................................142
8)....................................................142
4)....................................................142
5)....................................................142
9)....................................................142
10)..................................................142
SPECIFIC HOLISTIC OBJECTIVE:.......144
USES OF ESTERS................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds 145
acid halide......................................145
Ester................................................145
Anhydride.......................................145
Amide.............................................145
Nitrile.............................................145
acid + alcohol.................................146
ester + water...................................146
The ester functional group is:.........146
- 78 - Nomenclature of Organic Chemistry

R – COO –......................................146
R – COO – R'.................................146
Salt..................................................146
ethanoate ion (acetate)...................146
sodium ethanoate (sodium acetate) 146
Names.............................................146
Ester................................................146
Examples:.......................................147
Examples:.......................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate 147
Examples:.......................................147
( R – COO)X..................................148
Solved exercises on esters and salts :148
1)....................................................148
2)....................................................148
3)....................................................148
4)....................................................148
5)....................................................148
6)....................................................148
9)....................................................153
Examples:.......................................155
Examples:.......................................155
1)....................................................155
3)....................................................155
4)....................................................155
5)....................................................155
1) Write the formula of the following compounds: 156
1)....................................................158
6)....................................................158
7)....................................................158
either...............................................158
9)....................................................158
5)....................................................158
10)..................................................158
1)....................................................159
6)....................................................159
 Nomenclature of Organic Chemistry - 79 -

2)....................................................159
3)....................................................159
7)....................................................159
8)....................................................159
4)....................................................159
5)....................................................159
9)....................................................159
10)..................................................159
SPECIFIC HOLISTIC OBJECTIVE:.......162
SODIUM CYANIDE............................162
Examples:.......................................163
Aliphatic nitrile..............................163
Examples:.......................................163
Examples:.......................................163
Various exercises solved on nitriles.-164
Examples:.......................................164
cyclohexane carbonitrile................164
benzene carbonitrile.......................164
Examples:.......................................164
Examples:.......................................164
R – NO 2........................................166
Solved exercises on nitrocompounds.-166
PROPOSED EXERCISES.............167
1. Write the formulas for:............167
5......................................................168
1......................................................168
6......................................................168
2......................................................168
3......................................................168
7......................................................168
8......................................................168
4......................................................168
9......................................................168
1......................................................171
2......................................................171
7......................................................171
- 80 - Nomenclature of Organic Chemistry

3......................................................171
8......................................................171
4......................................................171
5......................................................171
9......................................................171
10....................................................171
2......................................................172
1......................................................172
6......................................................172
3......................................................172
8......................................................172
4......................................................172
9......................................................172
5......................................................172
10....................................................172
1......................................................173
2......................................................173
3......................................................173
4......................................................173
5......................................................173
8......................................................173
9......................................................173
10....................................................173
WEEBGRAPHY............................178

CH 3 CH 3 –C –CH 3
|
CH 3 –CH –CH 3
Nomenclature of Organic Chemistry - 81 -

7)
CH –CH
Yo
CH –CH –CH –CH –CH–CH –CH –CH
Yo Yo
CH CH –CH
Yo
CH –CH
Yo
CH
8)
CH 3 CH 3 CH 2 –CH 2 –CH –CH 2
–CH 3
| | | |
CH 3 –CH 2 –CH –CH 2 –CH –CH 2 –CH 2 –C –CH 3
CH 2 –CH 3 |
CH 3 –CH 2 –CH –CH 3
9)

SPECIFIC HOLISTIC OBJECTIVE:....................2

DIAMOND.................................................4
Hybrid state.................................................5
Carbon atom with sp 3 hybridization...........5

III. Name the following alkanes:

- 82 - Nomenclature of Organic Chemistry

h......................................................................8
ox....................................................................8
H%CxH...........................................................8
OX...................................................................8
h......................................................................8
saturated chain.............................................9
CH 3 –CH 2 –CH = CH 2................................9
Nomenclature 1979 Nomenclature 1993..9
Nomenclature 1979 Nomenclature 1993..9
CH 2 = CH–CH = CH 2.................................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name.................10
Systematic name trivial name.................10
Isomers are differentiated by the order in
which the atoms are bonded in the
molecule....................................................21
c) Isomerism of function : Different
functional group .......................................21
Huacaya X1 drilling rig (Chuquisaca)......23
SELF APPRAISAL :................................25
).................................................................25
SELF APPRAISAL : ORGANIC
CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:..................34
Characteristics of alkanes.- They are.....35
Example:...................................................35
Physical properties and uses of alkanes :. .35
3)...............................................................38
4)...............................................................38
5)...............................................................47
6)...............................................................47
8)...............................................................47
2,3,6–trimethylheptane (SI)......................47
10).............................................................47
11).............................................................48
Radicals or complex substituents.- They are
those substituents formed with primary and
secondary branches . To name them:........48
Nomenclature of Organic Chemistry - 83 -

basic alkyl group ......................................48

3. HE name the branch followed
secondary..................................................48
Examples:..................................................48
12).............................................................48
n–nonyl either nonyl...............................49
Examples:..................................................49
isobutyl......................................................49
Examples:..................................................49
Examples:..................................................49
Examples:..................................................50
Examples:..................................................50
ter -pentil either........................................50
Incorrect: 3.4, 6,7,8...................................51
Name: 8-ethyl-4-isopropyl-3,5,7-
trimethyldecane.........................................51
Example:...................................................51
Solved exercises on branched alkanes.-....51
5)...............................................................52
Name:........................................................52
4)...............................................................52
2,3,5-trimethyl-4-propylheptane...............52
YO. Write the semi-developed and
topological formulas of the following
alkanes:......................................................54
1)...............................................................54
2)...............................................................54
3)...............................................................54
4)...............................................................54
5)...............................................................54
6)...............................................................54
8)...............................................................60
9)...............................................................60
10).............................................................60
SELF APPRAISAL : ALKANES (II)....72
SPECIFIC HOLISTIC OBJECTIVE:..................84
Physical properties and uses of alkynes :..85
In the common system , they are named as
- 84 - Nomenclature of Organic Chemistry

derivatives of acetylene ............................85

Examples:..................................................85
Examples:..................................................85
Examples:..................................................86
2–pentine...................................................86
1–pentine...................................................86
1,3-butadiyne.............................................86
Acetylenic radicals or substituents.- They
are incomplete molecules of an alkyne:....87
Examples:..................................................87
Examples:..................................................87
Solved exercises on branched alkenes.-....87
5)...............................................................88
6)...............................................................88
PROPOSED EXERCISES........................91
YO. Write the semi-developed and
topological formulas of the following
alkynes:.....................................................91
II. There are errors in the following names
of alkynes, identify them, correct them and
write the correct name:..............................91
III. Write the semi-developed and
topological formulas of the following
alkenines:..................................................91
4)...............................................................93
5)...............................................................93
6)...............................................................93
ill...................................................................93
7)...............................................................93
9)...............................................................93
10).............................................................93
12).............................................................93
Yo..............................................................94
SELF APPRAISAL :................................95
SPECIFIC HOLISTIC OBJECTIVE:..................98
POLLUTION DUE TO HYDROCARBONS..98
1–cyclopropylbutane.................................99
Examples:..................................................99
Nomenclature of Organic Chemistry - 85 -

Examples:..................................................99
Correct: 1, 1,3..........................................100
YO. Write the formula corresponding to the
following cycloalkanes:..........................103
CYCLIC HYDROCARBONS (I)...........105
SELF APPRAISAL :..............................106
CYCLIC HYDROCARBONS (II)..........106
5...............................................................106
wJCE..............................................................106
SPECIFIC HOLISTIC OBJECTIVE:................108
FOOD ALLIES TO MAINTAIN YOUR
WEIGHT........................................................108
Physical properties of aldehydes and
ketones :..................................................109
Examples:................................................113
Common nomenclature.- Aldehydes are
named in three ways :..............................113
1. With their empirical names derived from
the corresponding carboxylic acids.........113
α-methyl- butyraldehyde.........................113
β-ethyl-γ-methyl -valeraldehyde.............113
Examples:................................................113
15)...........................................................114
16)...........................................................114
Aliphatic Aromatic Mixed....................115
Examples:................................................115
Examples:................................................116
4-methyl-3-penten-2-one........................116
Examples:................................................116
3-oxobutanal............................................116
2-oxobutanedial.......................................116
YO. Write the formula of the following
compounds:.............................................117
1).............................................................117
1...............................................................118
6...............................................................118
2...............................................................118
3...............................................................118
- 86 - Nomenclature of Organic Chemistry

4...............................................................118
9...............................................................118
F..............................................................118
10.............................................................118
SELF APPRAISAL :..............................120
3...............................................................120
4...............................................................120
5...............................................................120
6...............................................................120
8...............................................................120
9...............................................................120
10.............................................................120
1...............................................................121
CH— CH— CH— cO— CH— CH,......121
7...............................................................121
2...............................................................121
3...............................................................121
4...............................................................121
5...............................................................121
8...............................................................121
9...............................................................121
10.............................................................121
CONTENT:........................................................122
SPECIFIC HOLISTIC OBJECTIVE:................123
HOW TO REDUCE URIC ACID WITH
NATURAL REMEDIES................................123
Carboxyl group.......................................124
Aliphatic Aromatics.............................124
CH 3 –CH= CH – COOH...........................125
2-butenoic acid........................................125
3-carboxyhexanedioic acid.....................125
3-(1-carboxymethyl)hexaodioic acid......125
Examples:................................................125
2-methylbutenedioic acid........................126
Examples:................................................126
3-oxopentanoic acid................................126
Examples:................................................127
Nomenclature of Organic Chemistry - 87 -

CH 2 – COOH..............................................137
Some important carboxylic acids.-..........138
18)...........................................................138
YO. Write the formula of the compounds:
.................................................................139
II. Write the name of the compounds:.....139
1).............................................................139
2).............................................................139
3).............................................................139
4).............................................................139
5).............................................................139
6).............................................................139
7).............................................................139
8).............................................................139
9).............................................................139
10)...........................................................140
1).............................................................141
6).............................................................141
2).............................................................141
3).............................................................141
8...............................................................141
4).............................................................141
5).............................................................141
9).............................................................141
10)...........................................................141
1).............................................................142
6).............................................................142
2).............................................................142
CH-CH-CH-COOH.................................142
7).............................................................142
8).............................................................142
4).............................................................142
5).............................................................142
9).............................................................142
10)...........................................................142
SPECIFIC HOLISTIC OBJECTIVE:................144
USES OF ESTERS.........................................144
- 88 - Nomenclature of Organic Chemistry

Characteristics of carboxylic acid

derivatives.- Esters.......They are compounds
.................................................................145
acid halide...............................................145
Ester........................................................145
Anhydride................................................145
Amide......................................................145
Nitrile......................................................145
acid + alcohol..........................................146
ester + water............................................146
The ester functional group is:..................146
R – COO –...............................................146
R – COO – R'..........................................146
Salt..........................................................146
ethanoate ion (acetate)...........................146
sodium ethanoate (sodium acetate).........146
Names......................................................146
Ester........................................................146
Examples:................................................147
Examples:................................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate
.................................................................147
Examples:................................................147
( R – COO)X...........................................148
Solved exercises on esters and salts :......148
1).............................................................148
2).............................................................148
3).............................................................148
4).............................................................148
5).............................................................148
6).............................................................148
9).............................................................153
Examples:................................................155
Examples:................................................155
1).............................................................155
3).............................................................155
4).............................................................155
Nomenclature of Organic Chemistry - 89 -

5).............................................................155
1) Write the formula of the following
compounds:.............................................156
1).............................................................158
6).............................................................158
7).............................................................158
either........................................................158
9).............................................................158
5).............................................................158
10)...........................................................158
1).............................................................159
6).............................................................159
2).............................................................159
3).............................................................159
7).............................................................159
8).............................................................159
4).............................................................159
5).............................................................159
9).............................................................159
10)...........................................................159
SPECIFIC HOLISTIC OBJECTIVE:................162
SODIUM CYANIDE.....................................162
Examples:................................................163
Aliphatic nitrile.......................................163
Examples:................................................163
Examples:................................................163
Various exercises solved on nitriles.-.....164
Examples:................................................164
cyclohexane carbonitrile.........................164
benzene carbonitrile................................164
Examples:................................................164
Examples:................................................164
R – NO 2.................................................166
Solved exercises on nitrocompounds.-....166
PROPOSED EXERCISES......................167
1. Write the formulas for:....................167
5...............................................................168
- 90 - Nomenclature of Organic Chemistry

1...............................................................168
6...............................................................168
2...............................................................168
3...............................................................168
7...............................................................168
8...............................................................168
4...............................................................168
9...............................................................168
1...............................................................171
2...............................................................171
7...............................................................171
3...............................................................171
8...............................................................171
4...............................................................171
5...............................................................171
9...............................................................171
10.............................................................171
2...............................................................172
1...............................................................172
6...............................................................172
3...............................................................172
8...............................................................172
4...............................................................172
9...............................................................172
5...............................................................172
10.............................................................172
1...............................................................173
2...............................................................173
3...............................................................173
4...............................................................173
5...............................................................173
8...............................................................173
9...............................................................173
10.............................................................173
WEEBGRAPHY.....................................178

Yo
Nomenclature of Organic Chemistry - 91 -

CH –CH I
CH
- 92 - Nomenclature of Organic Chemistry

IV. Explain why each of the following names is

incorrect. To find the errors present in these
examples, draw their structures and write their
correct names.

1) 3-isopropyl-5,5-dimethyloctane

2) 2,2-dimethyl-3-ethylpentane

3) 3,5,6,7–tetramethylnonane

4) 2-dimethylpropane

5) 2,2,3–methylbutane

6) 2,2-diethyl-4,4-dimethylpentane

7) 3-propylpentane

8) 6-methyloctane

9) ter -butylmethane

10) 3-methyl-3-ethyl-4-methyldecane

11) 4-methylbutane

12) 2-methyl-5-isopropylheptane

13) 2-methyl-4-n-butyloctane

14) 2,3,3-trimethylbutane

15) 2,4,6,6-tetramethylheptane

16) 4-ethylhexane
Nomenclature of Organic Chemistry - 93 -

SELF APPRAISAL : ALKANES (I) SELF APPRAISAL : ALKYL RADICALS

1. The name of: CH 3 – CH 2 – CH 3 1. The name of: CH 3 –

a) propyl b) butane a) methyl b) methane

c) propane d) N. TO. c) ethyl d) N. TO.

2. The name of: CH 4 2. The name of: CH 3 – CH 2 – CH 2 –

a) methane b) ethane a) propenyl b) propyl

c) methyl d) N. TO. c) ethyl d) N. TO.

3. The name of: CH 3 – CH 2 – CH 2 – CH 3 3. The name of: CH 3 – (CH 2 ) 3 – CH 2 –

a) propane b) butane a) butenyl b) butyl

c) pentane d) N. TO. c) pentyl d) N. TO.

4. The name of: CH 3 – CH 3 4. The name of: CH 3 – CH 2 –

a) ethane b) mengano a) ethinyl b) ethyl

c) propane d) N. TO. c) propyl d) N. TO.

5. The name of: CH 3 – (CH 2 ) 5 – CH 3 5. The name of: CH 3 – (CH 2 ) 4 – CH 2 –

a) octane b) hexane a) hexyl b) ethyl

c) heptane d) N. TO. c) heptyl d) N. TO.

6. The name of: CH 3 – (CH 2 ) 6 – CH 3 6. The name of: CH 3 – CH 2 – CH 2 – CH 2 –

a) dean b) octane a) propyl b) tetrayl

c) nonane d) N. TO. c) butyl d) N. TO.

7. Linear 10-carbon alkane: 7. Give a name to the following radical:

a) hectane b) eicosane CH – CH – CH –
c) dean d) N. TO. Yo
CH
8. The name of: CH 3 – (CH 2 ) 3 – CH 3
a) 1-methyl-propyl or sec-butyl
a) pentagon b) pentane b) 1-methyl-propyl or isopropyl
c) pentyl d) N. TO. c) 1-methyl-propyl or tertbutyl
d) 1-methyl butyl
9. Linear alkane of 11 carbons
8. Give a name to the following radical:
a) undecane b) nonadecane
c) eicosane d) N. TO. CH – CH – CH – CH –
Yo
10. The name of: CH 3 – (CH 2 ) 4 – CH 3
CH 3
a) 3 – methyl –
a) bonano b) heptane or sec-pentyl
butyl
c) hexane d) N. TO. b) 3 – methyl – or isopentyl
c) 1 – methyl –
d) 1 – methyl –
pentyl 9. Name the following radical:

CH – CH – CH –
Yo
CH
- 94 - Nomenclature of Organic Chemistry

a) 1 –methyl– propyl eithersec-butyl c) 2,3-diethyl-butane d) 2,3-dimethyl-hexane

b) 2 –methyl–propyl eithersec-butyl 6. Name the following compound:
c) 2 –methyl– propyl eitherisobutyl
d) tert-butyl
CH – CH – CH – CH – CH I
CH –CH
10. Name the following radical:
CH a) 2-ethyl-pentane
Yo b) 2-methyl-
CH – C – c) 3-methyl-hexane pentane
Yo d) 2-ethyl-heptane
CH 7. The name of:

a) 1,1-dimethyl-ethyleithertertbutyl CH 2 –CH 3 I
b) 1,1-dimethyl-ethyleitherneobutyl CH 3 –CH –CH –CH 2 –CH –CH 3 I
c) 1,1 – dimethyl – ethylor sec-butyl
d) isopropyl CH 3 CH 2 –CH 2 –CH 3

SELF APPRAISAL : ALKANES (II) Yo

a) 2-methyl-3-propyl-5-ethyl-hexane
1. He name of:
b) 5-ethyl-2-methyl-3-propyl-hexane
CH 3 –CH –CH 3 c) 5-isopropyl-3-methyl-octane d) N.
Yo TO.
CH 3
a) methyl-propane b) butane 8. Name the following compound:
c) propyl-methane d) N. TO.
CH CH – CH
2. The name of:
CH 3 –CH –CH 2 –CH 3
Yo
CH 3
a) pentane b) ethyl-propane
c) methyl-butane d) N. TO.

3. The name of:

CH 3
Yo
CH – C – CH
Yo
CH 3
a) tetramethyl-methane b) dimethylpropane
c) pentane d) N. TO.

4. The name of:

CH 3 –CH –CH 2 –CH 2 –CH 3
Yo
CH 3
a) dimethyl-butane b) 2-methyl-
pentane
c) 4-methyl-pentane d) N. TO.

5. Name the following compound:

CH – CH – CH – CH
Yo Yo
CH CH

a) 2,3-methyl-butane b) 2,3-dimethyl-butane
 Nomenclature of Organic Chemistry - 95 -

SPECIFIC HOLISTIC OBJECTIVE:.............2

DIAMOND..........................................4
Hybrid state..........................................5
Carbon atom with sp 3 hybridization....5
h...............................................................8
ox.............................................................8
H%CxH....................................................8
OX............................................................8
h...............................................................8
saturated chain......................................9
CH 3 –CH 2 –CH = CH 2.........................9
Nomenclature 1979 Nomenclature 1993 9
Nomenclature 1979 Nomenclature 1993 9
CH 2 = CH–CH = CH 2..........................10
Nomenclature 1979 Nomenclature 1993 10
Systematic name trivial name..........10
Systematic name trivial name..........10
Isomers are differentiated by the order in which the atoms are bonded in the molecule. 21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)23
SELF APPRAISAL :.........................25
)..........................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:...........34
Characteristics of alkanes.- They are35
Example:............................................35
Physical properties and uses of alkanes : 35
3)........................................................38
4)........................................................38
5)........................................................47
6)........................................................47
8)........................................................47
2,3,6–trimethylheptane (SI)...............47
10)......................................................47
11)......................................................48
Radicals or complex substituents.- They are those substituents formed with primary and
secondary branches . To name them:. 48
- 96 - Nomenclature of Organic Chemistry

basic alkyl group ...............................48

3. HE name the branch followed secondary 48
Examples:...........................................48
12)......................................................48
n–nonyl either nonyl........................49
Examples:...........................................49
isobutyl...............................................49
Examples:...........................................49
Examples:...........................................49
Examples:...........................................50
Examples:...........................................50
ter -pentil either.................................50
Incorrect: 3.4, 6,7,8............................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:............................................51
Solved exercises on branched alkanes.-51
5)........................................................52
Name:.................................................52
4)........................................................52
2,3,5-trimethyl-4-propylheptane........52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
1)........................................................54
2)........................................................54
3)........................................................54
4)........................................................54
5)........................................................54
6)........................................................54
8)........................................................60
9)........................................................60
10)......................................................60
SELF APPRAISAL : ALKANES (II)72
SPECIFIC HOLISTIC OBJECTIVE:...........84
Physical properties and uses of alkynes : 85
In the common system , they are named as derivatives of acetylene . 85
Examples:...........................................85
Examples:...........................................85
Examples:...........................................86
 Nomenclature of Organic Chemistry - 97 -

2–pentine............................................86
1–pentine............................................86
1,3-butadiyne......................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:...........................................87
Examples:...........................................87
Solved exercises on branched alkenes.-87
5)........................................................88
6)........................................................88
PROPOSED EXERCISES.................91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write the
correct name:......................................91
III. Write the semi-developed and topological formulas of the following alkenines: 91
4)........................................................93
5)........................................................93
6)........................................................93
ill............................................................93
7)........................................................93
9)........................................................93
10)......................................................93
12)......................................................93
Yo.......................................................94
SELF APPRAISAL :.........................95
SPECIFIC HOLISTIC OBJECTIVE:...........98
POLLUTION DUE TO HYDROCARBONS 98
1–cyclopropylbutane..........................99
Examples:...........................................99
Examples:...........................................99
Correct: 1, 1,3...................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I)....105
SELF APPRAISAL :.......................106
CYCLIC HYDROCARBONS (II)...106
5........................................................106
wJCE.......................................................106
SPECIFIC HOLISTIC OBJECTIVE:.........108
- 98 - Nomenclature of Organic Chemistry

FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108

Physical properties of aldehydes and ketones : 109
Examples:.........................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde..................113
β-ethyl-γ-methyl -valeraldehyde......113
Examples:.........................................113
15)....................................................114
16)....................................................114
Aliphatic Aromatic Mixed.............115
Examples:.........................................115
Examples:.........................................116
4-methyl-3-penten-2-one.................116
Examples:.........................................116
3-oxobutanal.....................................116
2-oxobutanedial................................116
YO. Write the formula of the following compounds: 117
1)......................................................117
1........................................................118
6........................................................118
2........................................................118
3........................................................118
4........................................................118
9........................................................118
F.......................................................118
10......................................................118
SELF APPRAISAL :.......................120
3........................................................120
4........................................................120
5........................................................120
6........................................................120
8........................................................120
9........................................................120
10......................................................120
1........................................................121
CH— CH— CH— cO— CH— CH,121
 Nomenclature of Organic Chemistry - 99 -

7........................................................121
2........................................................121
3........................................................121
4........................................................121
5........................................................121
8........................................................121
9........................................................121
10......................................................121
CONTENT:.................................................122
SPECIFIC HOLISTIC OBJECTIVE:.........123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group................................124
Aliphatic Aromatics......................124
CH 3 –CH= CH – COOH....................125
2-butenoic acid.................................125
3-carboxyhexanedioic acid...............125
3-(1-carboxymethyl)hexaodioic acid125
Examples:.........................................125
2-methylbutenedioic acid.................126
Examples:.........................................126
3-oxopentanoic acid.........................126
Examples:.........................................127
CH 2 – COOH.......................................137
Some important carboxylic acids.-...138
18)....................................................138
YO. Write the formula of the compounds: 139
II. Write the name of the compounds:139
1)......................................................139
2)......................................................139
3)......................................................139
4)......................................................139
5)......................................................139
6)......................................................139
7)......................................................139
8)......................................................139
9)......................................................139
10)....................................................140
- 100 - Nomenclature of Organic Chemistry

1)......................................................141
6)......................................................141
2)......................................................141
3)......................................................141
8........................................................141
4)......................................................141
5)......................................................141
9)......................................................141
10)....................................................141
1)......................................................142
6)......................................................142
2)......................................................142
CH-CH-CH-COOH..........................142
7)......................................................142
8)......................................................142
4)......................................................142
5)......................................................142
9)......................................................142
10)....................................................142
SPECIFIC HOLISTIC OBJECTIVE:.........144
USES OF ESTERS..................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds 145
acid halide........................................145
Ester.................................................145
Anhydride.........................................145
Amide...............................................145
Nitrile...............................................145
acid + alcohol...................................146
ester + water.....................................146
The ester functional group is:...........146
R – COO –........................................146
R – COO – R'...................................146
Salt...................................................146
ethanoate ion (acetate).....................146
sodium ethanoate (sodium acetate). .146
Names...............................................146
Ester.................................................146
Nomenclature of Organic Chemistry - 101 -

Examples:.........................................147
Examples:.........................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate 147
Examples:.........................................147
( R – COO)X....................................148
Solved exercises on esters and salts :148
1)......................................................148
2)......................................................148
3)......................................................148
4)......................................................148
5)......................................................148
6)......................................................148
9)......................................................153
Examples:.........................................155
Examples:.........................................155
1)......................................................155
3)......................................................155
4)......................................................155
5)......................................................155
1) Write the formula of the following compounds: 156
1)......................................................158
6)......................................................158
7)......................................................158
either.................................................158
9)......................................................158
5)......................................................158
10)....................................................158
1)......................................................159
6)......................................................159
2)......................................................159
3)......................................................159
7)......................................................159
8)......................................................159
4)......................................................159
5)......................................................159
9)......................................................159
10)....................................................159
- 102 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:.........162

SODIUM CYANIDE..............................162
Examples:.........................................163
Aliphatic nitrile................................163
Examples:.........................................163
Examples:.........................................163
Various exercises solved on nitriles.-164
Examples:.........................................164
cyclohexane carbonitrile..................164
benzene carbonitrile.........................164
Examples:.........................................164
Examples:.........................................164
R – NO 2..........................................166
Solved exercises on nitrocompounds.-166
PROPOSED EXERCISES...............167
1. Write the formulas for:.............167
5........................................................168
1........................................................168
6........................................................168
2........................................................168
3........................................................168
7........................................................168
8........................................................168
4........................................................168
9........................................................168
1........................................................171
2........................................................171
7........................................................171
3........................................................171
8........................................................171
4........................................................171
5........................................................171
9........................................................171
10......................................................171
2........................................................172
1........................................................172
6........................................................172
 Nomenclature of Organic Chemistry - 103 -

3........................................................172
8........................................................172
4........................................................172
9........................................................172
5........................................................172
10......................................................172
1........................................................173
2........................................................173
3........................................................173
4........................................................173
5........................................................173
8........................................................173
9........................................................173
10......................................................173
WEEBGRAPHY..............................178

a) 4-ethyl-2,2,4-trimethyl hexane
b) 3-ethyl-3,3,5-trimethyl hexane
c) 4-ethyl-2,2,4-methyl hexane
d) 4- ethyl-2,2,4-triethyl hexane

9. Name the following compound:

SPECIFIC HOLISTIC OBJECTIVE:.............2

DIAMOND..........................................4
Hybrid state..........................................5
Carbon atom with sp 3 hybridization....5
h...............................................................8
ox.............................................................8
H%CxH....................................................8
OX............................................................8
h...............................................................8
saturated chain......................................9
CH 3 –CH 2 –CH = CH 2.........................9
Nomenclature 1979 Nomenclature 1993 9
Nomenclature 1979 Nomenclature 1993 9
CH 2 = CH–CH = CH 2..........................10
Nomenclature 1979 Nomenclature 1993 10
Systematic name trivial name..........10
- 104 - Nomenclature of Organic Chemistry

Systematic name trivial name..........10

Isomers are differentiated by the order in which the atoms are bonded in the molecule. 21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)23
SELF APPRAISAL :.........................25
)..........................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:...........34
Characteristics of alkanes.- They are35
Example:............................................35
Physical properties and uses of alkanes : 35
3)........................................................38
4)........................................................38
5)........................................................47
6)........................................................47
8)........................................................47
2,3,6–trimethylheptane (SI)...............47
10)......................................................47
11)......................................................48
Radicals or complex substituents.- They are those substituents formed with primary and
secondary branches . To name them:. 48
basic alkyl group ...............................48
3. HE name the branch followed secondary 48
Examples:...........................................48
12)......................................................48
n–nonyl either nonyl........................49
Examples:...........................................49
isobutyl...............................................49
Examples:...........................................49
Examples:...........................................49
Examples:...........................................50
Examples:...........................................50
ter -pentil either.................................50
Incorrect: 3.4, 6,7,8............................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:............................................51
Solved exercises on branched alkanes.-51
 Nomenclature of Organic Chemistry - 105 -

5)........................................................52
Name:.................................................52
4)........................................................52
2,3,5-trimethyl-4-propylheptane........52
YO. Write the semi-developed and topological formulas of the following alkanes: 54
1)........................................................54
2)........................................................54
3)........................................................54
4)........................................................54
5)........................................................54
6)........................................................54
8)........................................................60
9)........................................................60
10)......................................................60
SELF APPRAISAL : ALKANES (II)72
SPECIFIC HOLISTIC OBJECTIVE:...........84
Physical properties and uses of alkynes : 85
In the common system , they are named as derivatives of acetylene . 85
Examples:...........................................85
Examples:...........................................85
Examples:...........................................86
2–pentine............................................86
1–pentine............................................86
1,3-butadiyne......................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne: 87
Examples:...........................................87
Examples:...........................................87
Solved exercises on branched alkenes.-87
5)........................................................88
6)........................................................88
PROPOSED EXERCISES.................91
YO. Write the semi-developed and topological formulas of the following alkynes: 91
II. There are errors in the following names of alkynes, identify them, correct them and write the
correct name:......................................91
III. Write the semi-developed and topological formulas of the following alkenines: 91
4)........................................................93
5)........................................................93
- 106 - Nomenclature of Organic Chemistry

6)........................................................93
ill............................................................93
7)........................................................93
9)........................................................93
10)......................................................93
12)......................................................93
Yo.......................................................94
SELF APPRAISAL :.........................95
SPECIFIC HOLISTIC OBJECTIVE:...........98
POLLUTION DUE TO HYDROCARBONS 98
1–cyclopropylbutane..........................99
Examples:...........................................99
Examples:...........................................99
Correct: 1, 1,3...................................100
YO. Write the formula corresponding to the following cycloalkanes: 103
CYCLIC HYDROCARBONS (I)....105
SELF APPRAISAL :.......................106
CYCLIC HYDROCARBONS (II)...106
5........................................................106
wJCE.......................................................106
SPECIFIC HOLISTIC OBJECTIVE:.........108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:.........................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids. 113
α-methyl- butyraldehyde..................113
β-ethyl-γ-methyl -valeraldehyde......113
Examples:.........................................113
15)....................................................114
16)....................................................114
Aliphatic Aromatic Mixed.............115
Examples:.........................................115
Examples:.........................................116
4-methyl-3-penten-2-one.................116
Examples:.........................................116
3-oxobutanal.....................................116
 Nomenclature of Organic Chemistry - 107 -

2-oxobutanedial................................116
YO. Write the formula of the following compounds: 117
1)......................................................117
1........................................................118
6........................................................118
2........................................................118
3........................................................118
4........................................................118
9........................................................118
F.......................................................118
10......................................................118
SELF APPRAISAL :.......................120
3........................................................120
4........................................................120
5........................................................120
6........................................................120
8........................................................120
9........................................................120
10......................................................120
1........................................................121
CH— CH— CH— cO— CH— CH,121
7........................................................121
2........................................................121
3........................................................121
4........................................................121
5........................................................121
8........................................................121
9........................................................121
10......................................................121
CONTENT:.................................................122
SPECIFIC HOLISTIC OBJECTIVE:.........123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group................................124
Aliphatic Aromatics......................124
CH 3 –CH= CH – COOH....................125
2-butenoic acid.................................125
3-carboxyhexanedioic acid...............125
- 108 - Nomenclature of Organic Chemistry

3-(1-carboxymethyl)hexaodioic acid125
Examples:.........................................125
2-methylbutenedioic acid.................126
Examples:.........................................126
3-oxopentanoic acid.........................126
Examples:.........................................127
CH 2 – COOH.......................................137
Some important carboxylic acids.-...138
18)....................................................138
YO. Write the formula of the compounds: 139
II. Write the name of the compounds:139
1)......................................................139
2)......................................................139
3)......................................................139
4)......................................................139
5)......................................................139
6)......................................................139
7)......................................................139
8)......................................................139
9)......................................................139
10)....................................................140
1)......................................................141
6)......................................................141
2)......................................................141
3)......................................................141
8........................................................141
4)......................................................141
5)......................................................141
9)......................................................141
10)....................................................141
1)......................................................142
6)......................................................142
2)......................................................142
CH-CH-CH-COOH..........................142
7)......................................................142
8)......................................................142
4)......................................................142
 Nomenclature of Organic Chemistry - 109 -

5)......................................................142
9)......................................................142
10)....................................................142
SPECIFIC HOLISTIC OBJECTIVE:.........144
USES OF ESTERS..................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds 145
acid halide........................................145
Ester.................................................145
Anhydride.........................................145
Amide...............................................145
Nitrile...............................................145
acid + alcohol...................................146
ester + water.....................................146
The ester functional group is:...........146
R – COO –........................................146
R – COO – R'...................................146
Salt...................................................146
ethanoate ion (acetate).....................146
sodium ethanoate (sodium acetate). .146
Names...............................................146
Ester.................................................146
Examples:.........................................147
Examples:.........................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate 147
Examples:.........................................147
( R – COO)X....................................148
Solved exercises on esters and salts :148
1)......................................................148
2)......................................................148
3)......................................................148
4)......................................................148
5)......................................................148
6)......................................................148
9)......................................................153
Examples:.........................................155
Examples:.........................................155
1)......................................................155
- 110 - Nomenclature of Organic Chemistry

3)......................................................155
4)......................................................155
5)......................................................155
1) Write the formula of the following compounds: 156
1)......................................................158
6)......................................................158
7)......................................................158
either.................................................158
9)......................................................158
5)......................................................158
10)....................................................158
1)......................................................159
6)......................................................159
2)......................................................159
3)......................................................159
7)......................................................159
8)......................................................159
4)......................................................159
5)......................................................159
9)......................................................159
10)....................................................159
SPECIFIC HOLISTIC OBJECTIVE:.........162
SODIUM CYANIDE..............................162
Examples:.........................................163
Aliphatic nitrile................................163
Examples:.........................................163
Examples:.........................................163
Various exercises solved on nitriles.-164
Examples:.........................................164
cyclohexane carbonitrile..................164
benzene carbonitrile.........................164
Examples:.........................................164
Examples:.........................................164
R – NO 2..........................................166
Solved exercises on nitrocompounds.-166
PROPOSED EXERCISES...............167
1. Write the formulas for:.............167
Nomenclature of Organic Chemistry - 111 -

5........................................................168
1........................................................168
6........................................................168
2........................................................168
3........................................................168
7........................................................168
8........................................................168
4........................................................168
9........................................................168
1........................................................171
2........................................................171
7........................................................171
3........................................................171
8........................................................171
4........................................................171
5........................................................171
9........................................................171
10......................................................171
2........................................................172
1........................................................172
6........................................................172
3........................................................172
8........................................................172
4........................................................172
9........................................................172
5........................................................172
10......................................................172
1........................................................173
2........................................................173
3........................................................173
4........................................................173
5........................................................173
8........................................................173
9........................................................173
10......................................................173
WEEBGRAPHY..............................178
a) 7-ethyl-2,2,7-trimethyl octane
- 112 - Nomenclature of Organic Chemistry

b) 2-ethyl-2,7,7-trimethyl octane
c) 2,2,7,7–tetramethyl nonane
d) 2–ethyl–2,7,7–triethyl octane

10. The name of:

CH 3
Yo
CH 3 –C –CH 2 –CH –CH 3
Yo Yo
CH 3 CH 3

a) 2,2,4-tetramethyl-pentane
b) 2,2,4-trimethyl-pentane
c) 2,2-dimethyl-4-methyl-pentane d) N.
TO.
Nomenclature of Organic Chemistry - 113 -

Chap. 4

HYDROCARBONS
NOT SATURATED

ALKYNES
CONTENT:
- 114 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We value the use of unsaturated hydrocarbons in

technological processes, based on the study of the
properties and applications of alkynes, representing their
compounds through formulas and naming them according
to systematic and trivial nomenclatures to apply in solving
problems in the process of comprehensive training of the
student.

ACETYLENE AND ITS INDUSTRIAL USE IN

HYDROCARBONS

Acetylene, C 2 H 2 , is an energy-rich gas molecule that releases large amounts of derivatives when decomposed
into carbon and hydrogen.

Acetylene is an exothermic compound. This means that its decomposition into the elements releases heat, which
is why its generation usually requires high temperatures in some of its stages or the contribution of chemical
energy in some other way.

Acetylene was formerly used as a source of lighting and was discovered by the English chemist Edmond Davy in
1836. Its production grew widely starting in 1891 when the French chemist F. F. Moissan developed a method for
the large-scale preparation of calcium carbide using an electric furnace.

In addition, acetylene is a fuel with high energy efficiency and is very useful in a wide range of applications. It is
considered a multi-use gas in cutting and welding technology. Acetylene is always the correct alternative,
whether for cutting, welding or flame cleaning.

Another of the main uses of acetylene in modern industry is in autogenous welding and cutting steel parts with
an oxyacetylene torch. Since the flame temperature of such torches can rise to about 3,500 ºC, this tool has
come to be considered essential in mechanical work since it is used in the construction of bridges and steel
structures for buildings, repair and replacement of pipes. automotive exhaust, as well as in the manufacture and
repair of locomotives, automobiles, airplanes and many other machines.

Acetylene is also an important starting product in the chemical industry. Until the Second World War, a good part
of the synthesis processes were based on acetylene. Today it is losing more and more importance due to the
high energy costs of its generation.
Nomenclature of Organic Chemistry - 115 -

Characteristics of alkynes.- Alkynes are conditions, the fourth to the fifteenth are liquids and
hydrocarbons whose molecules contain at least one those with 16 or more carbon atoms are solids.
triple bond between carbon and carbon.
• The density of alkynes is less than 1, it increases as
the molecular weight increases.
They are also called acetylene , since the first term in
this series is called acetylene (C 2 H 2 ). • Its boiling point is a little higher compared to
alkenes.

• In the past it was used in lighting, as is the case with

miners' carbide lamps.

Ethyne is one of the major alkyne hydrocarbons, more

commonly known as acetylene .
Nomenclature of alkynes.- There are two ways of
It is used in the oxyacetylene torch, with which a naming, the common system and the systematic
temperature of 3000 °C can be reached. system (IUPAC).

It is ordinarily prepared by the reaction of calcium In the common system , they are named as
carbide with water : derivatives of acetylene .

Alkynes that have a single double bond in their First the radicals are named and at the end the word
acetylene.

CaC 2 + 2H 2 O CH ≡ CH + Ca(OH) 2 The simplest alkyne C 2 H 2 is called acetylene .

structure comply with the following formula: Examples:

1–ButIno (C 4 H 6 ) : CH ≡ C – CH 2 – CH 3
CH ≡ C – CH 3
7 CH ≡ CH acetylene
C n H 2n – 2
c ---(7C methyl acetylene
Example:

CH 3 – CH 2 – C ≡ CH CH 3 – C ≡ C – CH 3

Its structure presents carbon chains with sp ethyl acetylene dimethyl acetylene
hybridization for the pair of carbons that make the
double bond, here there is a sigma bond ( 7 ) and two
phi bonds ( 7 ). According to the IUPAC system , they are named the
same as alkanes, but replacing the suffix –ane with –
Physical properties and uses of alkynes : yne .

• Acetylene is a colorless gas, with a pleasant odor

when pure, but generally unpleasant because it
contains impurities such as phosphide and
hydrogen arsenide. It is slightly soluble in water and
very soluble in acetone. It burns with a very bright
flame due to the large proportion of carbon it
contains.

• It is also used in the preparation of numerous

compounds, such as acetaldehyde, ethanol, acetic
acid, isopropene, artificial rubber, etc.

• In the industry chemistry, the alkynes are

important for the production of PVC, artificial
rubber, etc.

• The first three alkynes are gases under normal

- 116 - Nomenclature of Organic Chemistry

Examples:

CH ≡ CH CH ≡ C – CH 3

ethyne tip
 Nomenclature of Organic Chemistry - 117 -

Starting with the fourth alkyne (butyne), the position

of the triple bond is indicated by a locator number
(the smallest possible).

Examples:

CH 3 – C ≡ C – CH 2 – CH 3

2–pentine

CH 3 – CH 2 – CH 2 – C ≡ CH

1–pentine

When there is more than one triple bond, the prefixes

di-, tri-, etc. are used.
Examples Branched alkynes.-
: CH ≡ C – C ≡ CH The IUPAC rules To
name these compounds
1,3-butadiyne they are:

1. The longest chain

CH ≡ C – C ≡ C – C ≡ that contains the triple
CH bond is chosen as the
1,3,5– 2. When the molecule has more than one triple bond,
hexatriyne the chain that contains the greatest number of triple
Examples of simple and multiple alkynes : bonds is taken as the main chain and
 - 118 - Nomenclature of Organic Chemistry

main chain. The 4. Univalent eno–yne

numbering must give radicals, the numbering
the smallest locators to must begin with the free
the triple bond. valence, the order of
Acetylenic radicals or arrangement of the
substituents.- They suffixes is – en – inyl.
are incomplete
molecules of an Examples:
alkyne:
– CH = CH – CH Ξ CH
1. If the radical has a
triple bond, its name 1–but in –3– inyl
has the ending –inyl or
–inyl .
– CH = CH – CH = CH – CH 2 – C Ξ CH
Examples:
2,4–octa dien –7– inyl
Solved exercises on
3 2 1 3 branched alkenes.-
H≡C– CH 3 –C C – CH = C –CH
Analyze and re-solve
nil or et the following examples:
nilo 1–prop inyl or 2–prop
1– propynyl 2– propynyl

2. When an alkane has

three hydrogens
reduced at one end, it is
assigned the ending –
ilidin or – illidino.

Examples:
H≡ CH 3 – CH ≡ CH 3 – CH

ilidin et ilidin prop ilidin

ther either either
ne met et ilidin ilidin

3. Substituents with
triple valence (ilidin)
and unsaturated
substituents with double
bond (enyl) change
their ending to –
enylidino or –
enylidino.

Examples:
propin iliden CH ≡ C—CH ═
butene ilidin CH 2 ═ CH—CH—C ≡
CH ≡ C—CH 2 —CH
pentin iliden
═
butene ilidin CH 3 – CH = CH – C ≡
Nomenclature of Organic Chemistry - 119 -
- 120 - Nomenclature of Organic Chemistry

5)
1 2 3 45 6
CH 3 – CH 2 – CC – CH 2 – CH – CH 2 – CH 3 I 8
9
7
CH 2 – CH – CH 3
Yo
CH 3

6-ethyl-8-methyl-3-nonyne

6)
1 2 3 4 5 6 7 8 9 10
CH 3 –CC–CC–CH –CH 2 –CC – CH 3
Yo

6-(2-butynyl)-2,4,8-decatriyne

CH 3 – CC – CH 2

4-ethyl-1-hexine

3,7-diethyl-6-methyl-1,4-
decadiino

Examples
:
1)

4,5,6-trimethyl-2-
octyne
 Nomenclature of Organic Chemistry - 121 -

Mixed unsaturated hydrocarbons.- They are

hydrocarbons that contain double and triple
bonds . They are called alkenines or enines .

1. If the hydrocarbon contains double and

triple bonds, proceed as follows:

2. The main chain is taken to be the one that

contains the greatest possible number of
multiple bonds, regardless of whether they are
double or triple bonds.

3. It is numbered so that the links together

take the lowest locators. If there is a double
bond and a triple bond at the same distance
from the ends , the double bond takes
precedence.

4. If all the possible chains contain an equal

number of carbon-carbon double and triple
bonds, the one that is longest is simply chosen
as the main one. If all the possibilities are of
equal length, continue with the following rules
to make the choice.

5. If the compound has a double bond and a

triple bond, the name ends in -en-yne ; if it has
two doubles and a triple, -dien-ino ; with two
triples and a double the ending is, -en-diino .
 - 122 - Nomenclature of Organic Chemistry

Main chain: The longest chain that contains the Solved eninos exercises.- Analyze and solve the
triple bond (pent- 1 - en- 4-yne ) following examples again:

1)
Numbering: When the double and triple bonds are
at the same distance from the end, the double bond 8 7 3 2 1
takes precedence.
CH 3 –CC–CH 2 –CH 2 –CH 2 –CH = CH –CH 3
Substituents: methyl in 3. .

– 1 – en – 4 – ino 2–nonen–7–ino
2)
Also: 3 –methyl– 1 –pent en –
7 6 5 4 3 2 1
CH c – CH 2 – CH =CH –C ≡CH
3-ethyl-4-(2-propynyl)-2,4-heptadiene
3–hepten–1,6–diyne
3)
1 2 3 4 5 6 7
CH C – CH = CH – CH = CH – CH 3

3,5-heptadien-1-yne
Main chain: The chain containing the double and triple 4)
bonds (oct -4 - ene - 1,7-diyne ). 9 8 76 5 43 2 1
CH 3 – CC – CC – CH = CH – CH = CH 2
Numbering: Since multiple links are at the same
time
same distance of both ends (1,4,7),
we number for that butyl takes the minor 1,3–nonadien–5,7–
locator ( 4 ).
Substituents: butyl in position 4 .

Name: 4 – butyl oct– 4 – en – 1,7 – diyne

Also: 4 – butyl – 4 –oct en – 1,7 – diyne

3-propyl-7-ethenyl-1,3-decadien-8-yne

4)
1
2
CH – CH 3
7 6 5 4 3 II
CH 3 –CH 2 –CH = C –C –CH 2 – CH 3
Yo
CH C– CH 2

Preference is given to double bonds over triple

bonds:

3 – methyl – 1,5 –
 Nomenclature of Organic Chemistry - 123 -

PROPOSED EXERCISES
YO. Write the semi-developed and topological II. There are errors in the following names of
formulas of the following alkynes: alkynes, identify them, correct them and write the
correct name:
1) 1-butyne
1) 1-methyl-1-propyne
2) 1,3-pentadiyne
2) 5,5-dimethyl-5-pentine
3) 3-ethyl-1,5-octadiyne
3) 2,5,5-trichloro-6-heptine
4) 6,9-diethyl-3-methyl-1,4,7-undecatriyne
4) 3,4-pentadiyne
5) ethyne or acetylene
5) 3-methyl-3,4-pentadiyne
6) 1,3,5-hexatriyne

7) 7,7-dimethyl-3-propyl-1,5-nonadiyne III. Write the semi-developed and topological

formulas of the following alkenines:
8) 5-ethyl-10-methyl-1,3,6,8-dodecatetraiino
1) 3–hepten–1,5–diyne
9) 3-propyl-1,5-heptadiene
2) 3-ethyl-3-methylpent-1-yne
10) 7,7-dimethyl-3-ethyl-4-nonyne
3) 3-ethynyl-4-hexen-1-yne
11) 3-propyl-1,5-heptadiyne
4) 3-methylpent-1-en-4-yne
12) 5-ethyl-5-isobutyl-3-octyne
5) 3-ethynyl-1,2-hexadien-4-yne
13) 3-isopropyl-5-methyl-1-hexyne
6) 2,4-dimethyl-1,3-octadien-5,7-diyne
14) 2,2,5-trimethyl-3-hexyne
7) 2,7-dimethyl-1,7-octadien-3,5-diyne
15) 2,5-dimethylhex-3-yne
8) 1,5–octadien–3,7–diyne
16) 3-tert-butyl-5-isobutylnonine
9) 2-propylocta-1,6-dien-4-yne
17) 2-bromo-5-ethyl-6-methyl-3-octyne
10) 4-ethyl-2,3-dimethylhex-1-en-5-yne
18) 4-butyl-1-chloro-8-ethyl-3-propyl-1,5,9-decatriyne
11) 5,7-decadien-2-yne
19) 1-bromo-2-methyl-2-(1,1-dimethylpropyl)-3-
hexyne 12) 8-methyl-1,3,8-nonatrien-6-yne

20) 3-(2-methylbutyl)-4-methyl-4-(1-ethylpentyl)-1,5- 13) 3-propyl-1,5-heptadiyne

heptadiyne
14) 3-octen-1,7-diyne
21) 4-tertbutyl-5-isobutyl-3,3,6,6-tetramethyl-1-
octyne 15) 4-methyl-3-vinyl-1,3-octadien-5,7-diyne

22) 7,7-dimethyl-3-isopropyl, 6-butyl-4-nonyne 16) 6-ethyl – 4 – ethenyl – 3,4-dimethyl-6-octen-1-

yne
23) 9-ethyl-5-isopropyl-2-methyl-7-propyl-3-dodecine
17) 2-ethyl-3-methyl-4-(1-methylethyl)-4-vinyl-1-
24) 4-secbutyl-3,5,6-trimethyl-2-nonyne tridecen–7,11–diino.

25) 7,7-dimethyl-3-isopropyl-6-butyl-4-nonyne 18) 8-ethenyl-7-ethyl-8-(3-methylbutyl)-10-vinyl-9,11-

tetradecadien–1,5–diyne
26) 9-ethyl-5-isopropyl-2-methyl-7-propyl-3-dodecine
19) 8-ethyl-3-propyl-6-isopropyl-9,13-dimethyl-11-
tert-butyl-2,11-pentadecadien-4-yne
- 124 - Nomenclature of Organic Chemistry

IV. Write the name of the following compounds:

V. Write the names of the following compounds:

CH 3
Yo
CH C – CH – CH 3
1)
Yo
c
ill
CH

2)
CH 3 –CH –CC–CH –CH 3
Yo
CH
CH – CH
Yo
CH 3 –CH 2 –CH 2 –CC–C –CH 2 –CH 3
3)
Yo
CH 2 –CH 2 –CH 3
 Nomenclature of Organic Chemistry - 125 -

4)

CH 3
Yo
CH 3 –CC–C –CH 2 –CH 3
Yo
CH 3

5)
CH 3
Yo
CH 2 = C – CH – CH – CC – CH 3
Yo Yo
CH 3 CH 3

6)
CH 3 –CH 2 –CH –CH 2 –CH 3
Yo
c
ill
CH
7)
CH 3

HC CH CC CH CH C CH

CH

8)
H 3 CC C- CH 2 - CH CH - CH
CH- CH 2H - CH
C
3
3 'CH 3

9)

H 3 C CH 2
H 3 C CH CH CH CH 2 C CH

10)
H C
2-CH 3
H C
3 -CC- CH - C CH - CH 2 - CH -CH
CH 3 CH 3

11)

CH 3 –(CH 2 ) 4 –C≡C–(CH 2 ) 5 –C≡C–

(CH 2 ) 3 –CH 3
12)
CH,
Yo
CH-CH,
Yo
CH,-CH-CH-CH- C=CH
II
CH, CH,
- 126 - Nomenclature of Organic Chemistry

Yo
CH,
Nomenclature of Organic Chemistry - 127 -

SELF APPRAISAL : ALKYNES (I)

1. The name –
of is: C
H2
C –
H C
3
H3
– I
CCH ≡ C – CH – C ≡ C –CH – CH
H 3 I

2 CH 3
– a) 6-
C
methyl-3-propyl-
H
1,4-heptadiyne
2
– b) 2-
C methyl-5-propyl-
≡ 3,6-heptadiyne
C c) 3-propyl-
H 6-methyl-1,4-
heptadiyne
d) N. TO.
a) 4–
pentine
4. The name of
b) 1–pentine is:
c) 2–
pentine CH 3 I
d) N. CH 3 –CH –CH 2
TO. –C –CH 3
Yo

2. The Yo
name of is: C
≡
CH 3 –C ≡ C CH
CH
–CH –CH 2 – 3
CH 3
Yo
a) 4-
CH 3
ethynyl-2,2-
a) 2-ethyl- dimethyl-
3-pentine pentane
b) 2,2,4-
b) 4-ethyl-2- trimethyl-5-
pentine hexyne
c) 4- c) 3,5,5-
methyl-2- trimethyl-1-
hexyne hexyne
d) N. TO.
d) N. TO. 6. The name of
is:

3. The name CH ≡ C –CH –

of is: CH 2 –CH 3
Yo
CH 2 CH 2 –
- 128 - Nomenclature of Organic Chemistry

C ≡ CH ethyl-2-methyl-
3,5-octadiyne
a) 4-ethyl- d) N. TO.
1,5-
hexadiyne
8. The name of
is:
b) 3-ethyl-1,5-
hexadiyne
c) 4- CH ≡ C –CH =
ethynyl-1- CH –CH = CH 2
hexyne
a) 3,5-
d) N. TO. hexadien-1-yne
b) 1-hexin-
3,5-diene
7. The name c) 1,3-
of is: hexadien-5-yne
d) N. TO.
CH 3 –CH –
C≡ 9. The name of
C– is:
C≡
CI
CH 2 = CH –CH –
Yo CH 2
CH 3 –C ≡
–CH 2 CH I
CH 3
CH 3 –CH –
CH 3 a) 3-methyl-
1-hexen-5-
a) 2,7- yne b) 4-
dimethyl-3,5- methyl-1-
nonadiyne hexin-5-ene
b) 3,8- c) 3-methyl-
dimethyl-4,6- 1-hexin-5-
nonadiyne ene d) N.
c) 7- TO.

5. The d) N
name of . TO. 10. The name of, is:
is:
C
CH 2 = H≡C–
CH –C CH =
≡ CH CH –CH
3

a) 1
-butyn- a) 1-
3-ene pentin-
b) 1 3-ene
-buten- b) 3-
3-yne penten-
c) 3 1-yne
-buten- c) 2-
1-yne penten-
Nomenclature of Organic Chemistry - 129 -

4-yne
d) N.
TO.
- 130 - Nomenclature of Organic Chemistry

SELF APPRAISAL : ALKYNES (II)

The name of is:

1. 6. H name of, is:
e
CH 3 –CH –C ≡ C –CH 3
2 CH ≡ C –CH –CH 2 –C ≡ CH I
C ≡ CH
a) 3-sudden b) 3-pentine
c) 2-pentine d) N. TO. 3-ethynyl-1,5-hexadiyne
3-(2-pentynyl)-1,4-pentadiyne
a) 4-ethynyl-1,5-hexadiyne
2. The name of is: b) N. TO.
c)
CH ≡ C – C ≡ C –CH 3 d)
name of, is:
a) 1,3-pentine b) 1,3-pentadiyne 7.
d) N. TO. H CH ≡ C –CH 2 –CH = CH –CH 3
c) 1,3-pentenyl
e

3. The name of is: 5. The name of is:

a) 2-hexen-5-yne b) 4-hexen-1-yne
c) 1-hexin-4-ene d) N. TO.
CH 3 –CH –C ≡ C –CH 3
Yo
CH 2 –CH 3 8. The name of is:

a) 4-methyl-2-hexyne b) 4-ethyl-2-pentine CH 3 –C ≡ C –CH = CH –CH 3

c) 2-ethyl-3-pentine d) N. TO.
a) 2-hexin-4-ene b) 4-hexen-2-yne
4. The name of is: c) 2-hexen-4-yne d) N. TO.

CH 3 –CH –CH 2 –C ≡ CH 9. The name of is:

Yo
CH 2 –C ≡ CH CH ≡ C –CH –CH = CH –CH 3 I
CH 2 –CH 3
a) 4-(2-propynyl)-1-pentine
b) 4-methyl-1,6-heptadiyne a) 3-ethyl-4-hexen-1-yne
c) 4-methyl-1,6-heptine
b) 4-ethyl-2-hexen-5-yne
d) N. TO.
c) 3-ethyl-1-hexin-4-ene
d) N. TO.
CH ≡ C –CH –CH 2 –CH 3 I CH 3
C ≡ CH
a) 4-methyl-2-hexin-4-ene b) 3-methyl-2-
a) 3-ethynyl-4-pentine hexen-4-yne c) 4-methyl-4-hexen-2-yne d)
b) 3-ethynyl-1-pentine N. TO.
c) 3-ethyl-1,4-pentadiyne
d) N. TO.
10. The name of is:

CH 3 –C ≡ C –C =CH –CH 3 I
Nomenclature of Organic Chemistry - 131 -

Chap. 5

ALICYCLIC HYDROCARBONS

HYDROCARBONS
CLOSED CHAIN
CONTENT:
- 132 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We promote the rational use of hydrocarbons to care for the

environment through research into the properties and
applications of hydrocarbons. alicyclic, representing their
compounds using formulas and naming them according to
systematic and trivial nomenclatures to apply in solving
problems in the student's comprehensive training process.

POLLUTION DUE TO HYDROCARBONS

Primary and secondary pollutants:

Pollutants due to hydrocarbons are divided into two large groups, with the criterion of whether they have
been emitted directly into the atmosphere by emission sources, such as automobiles, industry
chimneys, among others, or whether they have been formed in the atmosphere.
Primary pollutants:
Those coming directly from emission sources, for example: lead (Pb), carbon monoxide (CO), sulfur
oxides (SOx), nitrogen oxides (NOx), hydrocarbons (HC), particulate matter, among others.
Secondary pollutants:
Those originated in the air by the interaction between two or more primary pollutants, or by their
reactions with the natural components of the atmosphere. For example: ozone (O 3 ), peroxyacetyl
nitrate (PAN), hydrocarbons (HC), sulfates (SO 4 ), nitrates (NO 3 ), sulfuric acid (H 2 SO 4 ), particulate
matter (PM), among others. .
There are also polluting species that can be emitted directly and/or are formed during air transport. For
example, hydrocarbons, particulate matter, among others.
Nomenclature of Organic Chemistry - 133 -

Cycloalkanes.- They are saturated closed - chain or

cyclic hydrocarbons. Substances with rings from 3 to 30
carbon atoms are known.

For simple cycloalkanes the general formula is:

CnH2n

They are named by prefixing the prefix cyclo to the

name of the alkane with the same number of carbon
atoms.
If the substituent has more carbon atoms than the
Examples: cycloalkane, then the substituent is the main chain.

Example:

1–cyclopropylbutane

Polysubstituted cycloalkanes.- They have more than

one radical.

Nomenclature.- The IUPAC rules to name branched

cyclobutane cycloacanes, they are:

1. The ring substituents are numbered in such a way

that the lowest indices are obtained at the first point
Cyclohexane.- This molecule , due to maintaining the of difference.
tetrahedral angle (109º), is represented in two forms
(chair and boat), the most stable being the chair
conformation.

Conformations

cyclohexane chair boat

Cycloalkane radicals.- They are incomplete

cycloalkane molecules. They are named cycloalkanes
with the ending yl or yl .

Monosubstituted cycloalkanes.- They have a single

radical, it is not necessary to indicate its position.
- 134 - Nomenclature of Organic Chemistry

Examples:
Examples:

CH H2
2 C

cyclopropan cyclopropyl Correct : 1.3– Incorrect: 1.5–

e dimethylcyclohex dimethylcyclohex
cyclopropyl ane ane
 Nomenclature of Organic Chemistry - 135 -

4. The cycle with the largest size is the main group.

(Except if the cycle has a higher priority functional
group)

Correct: 1, 1,3
Incorrect: 1, 3,3
3-ethyl-1,1- 1–ethyl–3,3–
dimethylcyclopentane dimethylcyclopent
ane
2. Regardless of the locator number, the alphabetical
order is taken into account. The numbering continues to
give the smallest locator to the second substituent .
3. Use the prefixes di, tri, etc. for multiple identical

Examples
:

Cycloalkenes.- They are closed-chain or cyclic

unsaturated hydrocarbons that have at least one
double bond between C and C.

For simple cycloalkenes the general formula is:

C n H 2n–
2

Examples
:

cyclopropene cyclobutene cyclohexene

Nomenclature.- The IUPAC rules to name

cycloalkenes are:

1. The prefix “cycle” is added to the root of the chain

with the same number of carbon atoms.

2. The double bond ( = ) is assumed to be between

carbon 1 and 2.

3. When you have rings with various unsaturations ,

the carbons are numbered so that said bonds have the
substituents: lowest locators .

4. If the cycle has several substituents, they are

numbered so that they receive the lowest locators and
are named in alphabetical order.

5. When there is only one double bond, it is not

necessary to specify its position since it is understood
to be on carbon 1.
- 136 - Nomenclature of Organic Chemistry

6. When one of the carbons of the double bond has a bonds.

substituent; This carbon should always be considered Univalent radicals of cycloalkenes and
carbon 1, as shown in the following example: cycloalkynes.- They are derived from unsaturated
cyclic hydrocarbons by the loss of a hydrogen atom in a
Benzene - It is a cycloalkene, formed by 6 carbon
carbon atom.

They are named after the hydrocarbons from which

they come, replacing the ene and ino endings with
enyl(o) and inyl(o) , respectively.

The positions of double and triple bonds are indicated

by locators; The number 1 is assigned to the carbon
atom that has lost the hydrogen atom.

atoms and 6 hydrogen atoms, which has three double

Solved exercises on compounds
cycloalkanes.- Analyze and solve again:

1,3,5–cyclohexatriene (benzene)

Cycloalkynes.- They are closed - chain or cyclic

unsaturated hydrocarbons that have at least one triple
bond.

For simple cycloalkynes the general formula is:

C n H n–2

It is listed, starting with one of the carbon atoms of the triple bond, and continuing in the direction of the triple bond, in
the same way that it was used in cycloalkenes.
 Nomenclature of Organic Chemistry - 137 -

3) 4)

C/
1-methyl-1,3-
cyclopentadiene 1,3-cyclobutadiene

5) 6)
3
24
Us

1,4-cyclohexadiene
1,3,5,7–cyclooctatetraene

7) 8)
6/ 44 3—2

422 6,6-dimethyl-1,3-
) cycloheptadiene

4,5-dimethylcycloheptene

9) 10)
CH3
–CH 3
–CH2–CH3

1–methylcyclohexene 1-ethyl-5-methyl
cyclopentene

11) 12)
1
2

Solved exercises on cycloalkenes and CH 3 CH 3

cycloalkynes.- Analyze and solve the following
examples again: methylenecyclohexane
3,5-dimethylcyclohexene

13) 14)

Yes

vinyl cyclohexane
ethylidenecyclohexane
(ethenylcyclohexane)
- 138 - Nomenclature of Organic Chemistry

PROPOSED EXERCISES
YO. Write the formula corresponding to the 3) 4)
following cycloalkanes:

1) 4-isobutyl-1,1-dimethylcyclohexane

2) sec-butylcyclooctane

3) cyclopentylcyclohexane 5) 6)

4) 2,2-dimethyl-1-propylcyclopentane

5) dicyclohexylmethane

6) 1-isopropyl-3-methylcyclohexane 7) 8)
7) 1-cyclobutyl-2-cyclopropylethane

8) 1-ethyl-2-methyl-4-propylcyclohexane

9) butylcyclohexane
9) 10)
10) 2-cyclohexyl-4-cyclopropylhexane

11) 1-chlorocyclopentene

12) 3-methylcyclopentene
11) 12)
13) 3-cyclopropyl-2-pentene 9

14) 3,3-dimethyl- trans -cyclodecene

15) 3,3-dimethyl- cis -cyclodecene 13) 14)

16) ethinylcyclohexane

17) dichlohexyletine

18) 1-(2-butynyl)-3-methylcyclohexane
15) 16)
19) 1-(2,5-cyclohexadienyl)-2,5-cyclohexadiene.

20) 2,3-diphenyl-2-butene

(research phenyl in the next topic)

17) 18)
11. Name the following compounds:
EITHER'
1) 2)
Nomenclature of Organic Chemistry - 139 -
- 140 - Nomenclature of Organic Chemistry

SELF APPRAISAL : CYCLIC HYDROCARBONS (I)

1. The name of, is: a) 1,6-cyclooctadiene

CHa CH 2 b) 1,4-cyclooctadiene
c) 1,5-cyclooctadiene d) N.
CHa—CH TO.

a) cyclopropan b) cyclobutan
e cyclosquare
c) e N.
d)
TO.

2. The name of, is:

7. The name of, is:

a) 1-ethyl-1,2-dimethyl-cyclopentane
b) 2-ethyl-1,2-dimethyl-cyclopentane
c) 1,2-dimethyl-1-ethyl-cyclopentane
d) N. TO.
b) a) tricycloanane c)
cycloethane 8. The name of, is: cyclopropane
d) N. TO.
3. The name of, is:

a) 4-ethyl-3-methyl-
cyclopentene b) 4-ethyl-5-
a) cyclohexane b) benzene methyl-cyclopentene c) 5-
c) cyclohexagon d) N. methyl-4-ethyl-cyclopentene
TO. d) N. TO.
4. The name of, is: 9. The name of, is:

a) pentacyclane b) cyclopentagon
c) cyclopentane d) N. a) 1-ethyl-2,4,4-trimethyl-
TO. cyclohexane b) 4-ethyl-1,1,3-
trimethyl-cyclohexane c) 4-ethyl-
5. The name of, is: 1,1,5-trimethyl-cyclohexane d) N.
TO.

10. The name of, is:

a) 2-cyclohexene b) cyclohexene
c) cyclohexane d) N.
TO. a) 4,5-dimethyl-5-ethyl-
cyclohexene b) 5-ethyl-4,5-
6. The name of, is: dimethyl-cyclohexene c) 4-ethyl-
4,5-dimethyl-cyclohexene d) N.
TO.
 Nomenclature of Organic Chemistry - 141 -

SELF APPRAISAL : CYCLIC HYDROCARBONS (II)

1. The name of, is: 6. The name of, is:

a) 1,2,3-trimethyl- a) 2,4-dimethyl-1,3-cyclohexadiene
cyclopentane b) 2,4-dimethyl-2,4-cyclohexadiene
b) 1,2,3-cyclotrimethyl- d) N. c) 1,3-dimethyl-1,3-cyclohexadiene d) N.
pentane TO. TO.
2. c)
The name of is:
1,2,3-trimethyl-cyclopentyl 7. The name of, is:

a) 1-ethyl-3,4-dimethyl- a) 2,6-dimethyl-1,3-cyclohexadiene
cyclohexane b) 2,6-dimethyl-1,3-cycloheptadiene
b) 1,2-dimethyl-4-ethyl- d) N. c) 1,5-dimethyl-3,5-cycloheptadiene d) N.
cyclohexane TO. TO.
3. c)The name of is:
4-ethyl-1,2-dimethyl-
cyclohexane 8. The name of is:

CE3_CE,

wJCE
a) 1,2,3-trimethyl-4- a) 1,2,4-trimethyl-cyclohexane
cyclohexene b) 1,2,4-trimethyl-cycloheptane
b) 3,4,5-trimethyl-cyclohexene d) N. c) 1,3,4-trimethyl-cyclohexane d) N.
c) 4,5,6-trimethyl-cyclohexene TO. TO.
4. The name of is:
9. The name of is:

EC,. NUCE,

a) 1,4-dimethyl-2,4-cyclohexene
and I CH-CH
b) 1,4-dimethyl-2,4- a) 2-ethyl-1,6-dimethyl-1,3,5-cyclooctatriene
cyclohexadiene d) N. b) 1-ethyl-2,5-dimethyl-1,5,7-cyclooctatriene
c) 2,5-dimethyl-1,3- TO. c) 5-ethyl-1,6-dimethyl-1,3,5-cyclooctatriene d) N.
5. cyclohexadiene
The name of is: TO.
10. The name of, is:

a) 2-ethyl-1-ethynyl-4-methyl-
a) 1,3,5-trimethyl-4,6-cyclononadiene
cyclohexane
b) 1,3,5-trimethyl-4,6-cyclooctadiene
b) 1-ethynyl-2-ethyl-4-methyl- d) N. c) 3,5,7-trimethyl-1,3-cyclooctadiene d) N.
cyclohexane TO. TO.
c) 3-ethyl-4-ethynyl-1-methyl-
cyclohexane
- 142 - Nomenclature of Organic Chemistry

Chap. 9

CARBONYLIC COMPOUNDS

ALDEHYDES AND KETONES

CONTENT:
Nomenclature of Organic Chemistry - 143 -

SPECIFIC HOLISTIC OBJECTIVE:

We highlight the presence of carbonyl compounds in the

chemical products industry, describing the properties and
applications of carbonyl compounds, compound formation
and nomenclature, differentiating aldehydes from ketones
to apply in solving problems in the integral formation
process of the student.

FOOD ALLIES TO MAINTAIN YOUR WEIGHT

If you are in the process of changing your diet, because you need to lose weight, for health, or improve your
eating habits.

Don't stop eating fish. Salmon and tuna are high in protein and omega 3, essential for preventing chronic
diseases.

On the other hand, skim milk, yogurt and cheese are sources of calcium, magnesium and vitamin D, these
foods provide protein to the muscles.

In addition, seeds such as walnuts and almonds provide "good" fats, promoting cardiovascular health and a
balanced weight.

Whole grains are considered the body's fuel due to their contribution of carbohydrates and fiber for good
digestive health.

Garlic is a natural antibiotic against the microorganism that causes many cases of gastritis. Fights
hypertension and high cholesterol.

Tomato is said to delay aging, protect the eyes, hydrate and prevent cramps and muscle contractures and of
course water.

Nuts and peanuts help your heart health

- 144 - Nomenclature of Organic Chemistry

Characteristics of aldehydes and ketones.-

Aldehydes and ketones are compounds that contain
the carbonyl functional group in their structure.

Ketones are widely distributed in nature:

Acetone and methyl ethyl ketone are widely used in

industry as solvents.

In domestic life, acetone is the solvent par excellence

for nail paints and a mixture of both is used as a
solvent-cement for PVC pipes.

Physical properties of aldehydes and ketones :

• Aldehydes that are in liquid state range from C 2 to

C 12
• Ketones are find in state
liquid from C 3 to C 12
• The density of aldehydes and ketones increases
according increases he
number of carbons in the alkyl group.
• They are less dense than water.

Aldehydes are organic compounds used to obtain:

• They are soluble in water and other polar solvents.
• Its solubility decreases as the alkyl group increases.
Germicides, sample preservatives, such as insulators • Have boiling points intermediate
(bakelite). between alcohols and alkanes.

The manufacture of resins, plastics, solvents, paints,

perfumes, antiseptics and essences. Carbonyl group.- The functional group known as the
carbonyl group is a carbon atom linked to an oxygen
Methanal or formic aldehyde is the most widely used atom by a double bond, leaving two bonds free to
aldehyde in industry; it is used mainly to obtain combine.
phenolic resins and in the production of explosives, as
well as in the production of alkyd resins and expanded EITHER
polyurethane. II
–C –
It is also used in the production of one of the so-called
technical plastics that are mainly used to replace
metal parts in automobiles and machinery, as well as
for impact- resistant covers in the manufacture of Structurally, aldehydes and ketones are similar. The
electrical appliances. These plastics are called POM difference consists of the following:
(polyoxymethylene). – CO –
Aldehydes have a hydrogen atom
Many aldehydes and ketones are part of the natural attached to the carbonyl group :
aromas of flowers and fruits, which is why they are
used in perfumery to produce aromas, such as
EITHER
benzaldehyde (smell of bitter almonds), anisic
aldehyde (essence of anise), vanillin, piperonal II
(sassafras essence), cinnamic aldehyde (cinnamon R –C –H
essence).
Nomenclature of Organic Chemistry - 145 -

Examples atoms:
:

EITHER
II
R – C – R'
Aldehydes.- Aldehydes are compounds with the
carbonyl functional group at one end of the chain.

Functional General
Formula
group name

C=O R – CHO Aldehyde

In ketones the carbonyl is bonded to two carbon

Classification of aldehydes.- Depending on the

Examples type of hydrocarbon radical attached to the functional
: CH 3 –
group, aldehydes can be: Ethanal
CHO Ethan
Aliphatic aldehyde Aromatics

R – CHO Ar–CHO

IUPAC nomenclature or systematics of

aldehydes.- Aldehydes are named by replacing the
–ane ending of the alkane with –al .

1. It is not necessary to specify the position of the

When the carbonyl group is at one end of the aldehyde group, since it occupies the end of the chain
chain, you have an aldehyde, in this case the (locator 1).
carbon will beEITHE
linked to a hydrogen atom and an
R
alkyl or aryl group. R – CHO When the string contains two aldehyde functions, the
II suffix –dial is used.
When the carbonyl
R –C group is within the chain, we
have a ketone –Hand the carbon will be linked on
both sides to alkyl or aryl groups. Examples
:

Examples H–CHO CH – CH – CHO

:
CH 3 –CH 2 –CHO CH 3 –CO –CH 3 metanal Propanal
F N
o a CHO–CHO CHO–CH –CH –CHO
propanal propanone
r m
(aldehyde (ketone)
m e EITHER
) EITHER EITHER
u s EITHER
l
a
etanodial butanedial
- 146 - Nomenclature of Organic Chemistry
Nomenclature of Organic Chemistry - 147 -

2. If there are double or triple bonds, the

name ends in enal , inal , the position of the links is 4. The “–CHO” group is read as a substituent,
indicated with the corresponding numbering. when there are three or more aldehyde groups in a
chain or when other functional groups have priority in
Examples: the nomenclature; the –CHO group is called formyl
or formyl.
CH 2 = CH –CH 2 –CH 2 –CHO Examples:

EITHER CHO –CH –CH –CH –CHO I CHO

3–formylpentanedial
4–pentenal

CHO –CH –CH –CH –CHO

CHO–CH –CH –CH –C= CH Yo
CH
5–hexinal Yo
CHO

3. The branching chains are named from the aldehyde 3–formylmethylpentanedial

functional group and the substituents following the rules
already known.
5. If the carbonyl group –CO– is found within the
The carbonyl group –CO– , has preference over chain, it is called oxo. The numbering
radicals, unsaturations and alcohols, and the compound It begins with the most important group, naming the
must begin to be numbered at the end where said radicals alphabetically first.
carbonyl group is found.
Examples:
Only when there are carbonyl groups at both ends are
the criteria on alcohols, unsaturations and radicals taken
4 32 1
into account to decide where to start numbering the
chain.
CHO–CH–CH– COOH

Examples: 4- oxo butanoic acid

either
3-formylpropanoic acid
CH 3 I
CHO–CH = CH –CH –CH 3
32 1
CHO–CH–CH– COOH
Yo
4-methyl-2-pentenal
CHO

CH 3 –CH 2 –CH –CH –CHO 3,3 – diformylpropanoic acid

Yo Yo
CH 3 CH 2 I
CH 6. If the –CHO group is attached to a ring, first write
the name of the ring followed by the suffix –
carbaldehyde . Cycle numbering is done by giving
2-ethyl-3-methylpentanal
locator 1 to the carbon of the cycle that contains the
aldehyde group.

Examples:
- 148 - Nomenclature of Organic Chemistry

acrolein
CH 2 = CH –CHO

malonaldehyde
CHO –CH 2 –CHO

CHO – CHOH – CH 2
glyceraldehyde
OH

CHO

benzaldehyde

2. Another way to name aldehydes is to use the

Greek alphabet to indicate the position of the
substituents. It begins with the letter alpha (α) from the
second carbon that is next to the aldehyde group (–
CHO)

Examples:
Note : Carbaldehyde is
used when the aldehyde
is a functional group –(CH
, 2 ) 3 –CHO
while formyl is used valeraldehyde
when it acts as a (Comes from pentanoic aci
substituent .

Common
nomenclature.-
Aldehydes are named
in three ways :

1. With their empirical

names derived from
the corresponding
carboxylic acids.

Examples:
Formula Common name

H–CHO
formaldehyde or formalin
(Comes from formic acid)

acetaldehyde
CH–CHO
(Comes from acetic acid)

CH –CH –CHO
propionaldehyde
(Comes from propionic acid)

butyraldehyde
CH 3 –(CH 2 ) 2 –CHO
(Comes from butanoic acid)
Nomenclature of Organic Chemistry - 149 -

Examples:
% AND
CHO –CH –CH 2 –CH 3
Yo
CH 3

α-methyl-
butyraldehyde

S YB«
CH 3 –CH –CH –CH 2 –
CHO
Yo Yo
CH 3 CH 2
Yo
CH 3
β-ethyl-γ-methyl -
valeraldehyde

3. Derived system.-
Aldehydes are named
as derivatives of
acetaldehyde ; as if the
H of its methyl group had
been replaced by alkyl
radicals.

CH 3 – CH 2 –CHO CH 3 –CH 2 – CH 2 –CHO

methyl acetaldehyde ethyl acetaldehyde

- 150 - Nomenclature of Organic Chemistry

Solved exercises on aldehydes.- Check the 10)

following examples:
CHO –C C–CH –CH = CH –CHO
Yo
1)
CH
CH C–CHO
2–propinal 4-methyl-2-hepten-5-inal

2) 11)
CH – CHOH –CH –CHO CH 3
Yo
3-hydroxybutanal CH 3 –CH –C –CH 2 –CH 2 –CHO I Yo
OH CH 3

5-hydroxy-4,4-dimethylhexanal
3)
12)
– CH – CH – CHO
CH 3
4) Yo

CHO –CH –CH –CH –CHO I CHO –CH–C –CH 2 –CH 2 –CHO I Yo
CHO OH CH 3

3–formylpentanedial
2-hydroxy-3,3-dimethylhexanedial
5)
CHO–CH –CH –CH–CHO I Yo
CH CHO 13)
CH
Yo
2-formyl-4-methylpentanedial CHO –CH –C –CO –CH 2 –CHO I Yo
OH CH 3
6)
COOH – CH – CH – CH – COOH I
CHO 2-hydroxy-3,3-dimethyl-4-oxohexanedial

3-formylpentanedioic acid 14)

CHO –CH 2 –CH 2 –CH 2 –CH –CH 2 –CH 2 –CH 2 –CHO I
CH 2
Yo
7) CH – CHO
OH I
CH OH – CH – CHO
5–(2–
2,3-dihydroxypropanal formylethyl)
1 1
nonanodial
5 6
) O )
8) H

OH 3- p
Yo hydr r
1 oxyp 1 o
CH – CH – CH – CHO p
7 ropa 8 E
) nal ) a I
2-hydroxybutanal n T
e H
9) d2 E
2–
CHO–CO –CH –CH –CH bro i– R
mo ap
hex lr
2-oxopentanal
ana o
l p
i
n
Nomenclature of Organic Chemistry - 151 -

Classification of ketones.- Depending on the type of

radical attached to the functional group, ketones can
be:

Aliphatic Aromatic Mixed

R–CO–R' Ar–CO–Ar' R–CO–Ar'

Systematic nomenclature of ketones.- According to the

IUPAC rules:

1. Ketones are named like normal hydrocarbons with

the ending –one and indicating the position of the
carbonyl group “–CO–”.

If there are two or more ketone groups, the suffix –

dione , trione , etc. is used.

Examples:

CH
1 3 –CO–CH
23 3 45 Propanone Aceton
CH 3 –CO –CH 3 CH 3 –CO –CH 2 –CO –CH 3

propanone 2,4-pentanedione

Ketones.- In ketones ,
the carbonyl is linked to
two radicals that can be
the same, different, alkyl
or aromatic.

EITHER

II

R – C – R' R–
CO – R'

Ketones carry the

carbonyl functional
group inside the chain.

Functional group Formula General name

C=O R–CO–R'

Formula Names
- 152 - Nomenclature of Organic Chemistry

2. If there are double or

triple bonds, you must
begin by indicating the
position of the
unsaturation ending in –
en , –in . Then the
position of the carbonyl
and the chain with the
suffix ona .

Examples:

3.
Branc
hing
chains
are
named
the
same
as
hydroc
arbons
,
substit
uents
in
alphab
etical
order.
Nomenclature of Organic Chemistry - 153 -

The carbonyl group –CO– has preference over Nomenclature common .- HE they name
radicals, unsaturations and alcohols. alphabetically the radicals attached to the carbonyl
functional group accompanied by the word ketone .
Examples:
Examples:
CH 3 –CO –CH =C –CH 3 I
CH 3

4-methyl-3-penten-2-one

CH – CH –CO –CH –CO –CH –CH

Yo Yo
CH 2 CH 3
Yo
CH

4-ethyl-2-methyl-3,5-heptadione

4. The ketone function has priority over alcohols,

phenols, radicals and unsaturations, but it does not
have priority over aldehydes. When found in a chain
with an aldehyde , the ketone is considered the
substituent; To indicate the oxygen atom of the
carbonyl group of the ketone, the prefix “ oxo– ” is
used.

Examples:

CH 3 – CO –CH 2 –CHO

3-oxobutanal

CHO – CO –CH 2 –CHO

2-oxobutanedial

5. If the carbonyl group “ –CO– ” is attached to a ring,

the name of the ring is written with the ending one .

CH 3 –CO –CH 3 CH 3 –CO –CH 2 –CH 3 ethyl

dimethyl ketone methyl ketone

( acetone )
- 154 - Nomenclature of Organic Chemistry

or – CO – or
(©) – CO –CH 3
diphenyl ketone
phenyl methyl ketone (benzophenone)
(acetophenone)

II O II O

ethyl phenyl ketone (1- ethyl isopropyl ketone (2-

phenyl-1-propanone) methyl-3-pentanone)

C 8 H 17 – CO – C 9 H 19
© –CO – ©
nonyl octyl ketone
diphenyl ketone
( benzophenone )

(© –CO –CH (©) –CO –CH

ethyl phenyl ketone phenyl propyl ketone (

( propriophenone ) butyrophenone )
EITHER
II

II O

3-penten-2-one 3,5-dimethyl-4-heptanone
OO
II II
EITHER

II or
3,5-heptanedione
2,5-cyclohexadienone
 Nomenclature of Organic Chemistry - 155 -

PROPOSED EXERCISES
YO. Write the formula of the following compounds: 1)
CHO –CH –CH = CH –CH –CHO
1) 3-ethyl-2-methylhexanal

2) 5-ethenyl-2,6-heptadienal

3) 3-hepten-5-inal
2)
4) 3-phenyl-2-propenal
CH –CH –CH –CH –CH –CHO
5) 2-hydroxy-3,5-dioxohexanal Yo Yo
CHO CHO
6) 2,3-dioxo-4-pentinal 3)
CH 2 =C –CH 2 –CO –CH 2 –CO –CH 3
7) 3,5-diformylheptanedial 1
I CH 2 –CH 3
8) 2-methyl-3-oxopentanal
4)
9) 2-methyl-3-pentanone
CH 3 –CO –CH 2 –CO –CH 2 –CH 3
10) 4-methyl-2-pentanone 5)

11) 3,6-dioxoheptanal CH C –CH 2 –CO –CH 2 –CHO

6)
12) 1-hepten-5-in-3-one
CH = CH –C
2 C–CHO
13) 4-methyl-2-cyclohexenone 7)

14) 4-chloro-4-fluoro-2-hydroxy-2,3-
dimethylpentanedial © –CH 2 –CH 2 –CHO
8)
15) 2-methyl-4-ethyl-5-hydroxyoctanedial
CH 2 –CO –CO –CH 3
16) 3-oxo-pentanal

17) 3-phenyl-2-propinal 9)

18) 2,3-dihydroxypropanal CH 3 –C = CH –CH 2 –CH –CHO

Yo Yo
19) 2,4–diformylpentanal CH 3 CH 2
1
CH 3
20) 2,3–diformylhexanodial
10)
21) 2,5–dioxooctanedial CH 3 –CH 2 –CO –CH –CH 3
1
22) benzene–carbaldehyde
CH 3
23) 3-chloro-4-methylpentanal 11)

24) 4-hydroxy-cyclohexanecarbaldehyde CH 3 –CH 2 –CH –CO –CH 3

CH 3 –CH 2
25) 3-nitro-benzaldehyde
12)
26) 4-oxo-2-hexenal
CH 3 –CH –CH 2 –C –CH 3
27) 3-oxo-butanal Yo II
CH 3 EITHER
28) 4-hydroxybut-2-en-1-al

II. Write the name of the following compounds:

- 156 - Nomenclature of Organic Chemistry

SELF APPRAISAL : ALDEHYDES (I)

1. 6.
CH –CH –CHO CE,= CH — CHO

a) propanol
a) tip
b) propanal
b) ethenal
c) ethanal
c) propenal
d) N. TO.
d) N. TO.

2.
OHC—CH — CH- CHO

a) butanedial a) 2-pentendial
b) etanodial b) 3-pentendial
c) butanal c) 3-pentendiol
d) N. TO. d) N. TO.

3.
✓°
CH—CH,—CH,—cK
PH
a) 2-hexinal
b) 4-hexinal
a) propanal
c) 1-hexinal
b) butanal
d) N. TO.
c) butanol
d) N. TO.
4.

//
EITHER cs,
CH – C 3 H a) 2,2-dimethylbutanal

a) metanal b) 3,3-dimethylbutanal
b) methanol c) 3,3-dimethylbutanol
c) ethanal d) N. TO.
d) N. TO.

10.
5.
CH,SH-CEO

cs,
a) 2-propylmethanal
b) 1-methylpropanal a) 3-phenyl-5-pentinal b) 3-phenyl-1-
c) 2-methylpropanal pentinal c) 3-phenyl-4-pentinal d) N. TO.
d) N. TO.
9.

F
CH— CH— C— CHO
 Nomenclature of Organic Chemistry - 157 -

ALDEHYDES (II)

6.
SELF APPRAISAL :
■ CHO OHC — CH,- C=c- CH— CHO

1. a) 3-hexinodial
b) 3-hexenodial
CH-CH—CH,- c) 3-hexinediol d) N. TO.

a) butanol
b) butanal 7.
c) butanone H—CHO OHC—CH—CH—CHO
d) N. TO. 2 2।
CHO
2.
a) 3-formylbutanedial
OEC—CH,—CH-C b) 2-hydroxybutanedial
c) 2-formylbutanedial
d) N. TO.
a) pentanedial
b) pentanediol
c) pentanal H,—CHO 8.
d) N. TO. CH—CH—CH—CH—CHO
3 - 1 -

3. CHO
OHC-CH-CHa-' CH
a) 3-formyl-pentanal
b) 2-ethyl-butanedial
a) 2-methyl-pentanediol c) 3-ethyl-butanedial d) N. TO.
b) 1-methyl-pentanedial
c) 2-methyl-pentanedial
d) N. TO. "CHO 9.
CH3 CH 2 OH — CHa CHO

4. a) 3-formyl-butanal
CH,—CH- CH - CH, b) 2-hydroxy-butanal
c) 3-hydroxy-butanal d) N. TO.
a) 2-methyl-butanal
b) 3-methyl-butanal 10.
c) 2-formyl-butane
d) N. TO. CH— 0— CH— CHO
,CHO 3 -
a) 3-oxybutanal
5. b) 3-oxobutanal
CH—CH_CH— CH. 3 2 c) 3-oxabobutal
d) N. TO.
a) 2-pentenal
b) 3-pentenal
c) 3-pentenol
d) N. TO.
- 158 - Nomenclature of Organic Chemistry

SELF APPRAISAL : KETONES (I)

6.
CH- CE— CH—CO—CH,
CE-CH,
a) 3-ethyl-4-pentanone
a) dimethyl b) 3-ethyl-1-pentanone
acetone c) 3-ethyl-2-pentanone
b) propanal d) N. TO.
c) propanone
d) N. TO.
7.
either
II
CH,- c — CH CH CH

a) 2-pentanone
e) propanone b) methyl ethyl ketone
f) ethyl methyl c) 2-butanone
ketone c) methyl d) N. TO.
ethyl ketone d) N.
TO.
8.
3. CH, CO — CH- CH— CO —
CH,

EC,
a) 1-penten-4-one
b) 4-penten-2-one
a) 4-methyl-2,5-hexanedione
c) 4-pentenone
b) 3-methyl-2,5-hexanedione
d) N. TO.
c) 4-methyl-2,4-hexanedione
d) N. TO.
4. 9.

a) dipropyl ketone
a) phenyl ketone
b) 3-butanone
b) benzenone c)
c) 3-pentanone
cyclohexanone d)
d) N. TO.
N. TO.

5.
10.
CH—CH— CO — CH— CE,

C,
a) 2-methyl-3-pentanone
b) 4-methyl-3-pentanone
c) ethyl vinyl ketone a) 2-ethyl-3-oxo-
d) N. TO. pentanedial b) 4-ethyl-3-
oxo-pentanedial c) ethanal
2-butanal ketone d) N. TO.
 Nomenclature of Organic Chemistry - 159 -

SELF APPRAISAL : KETONES (II)

1. d) N. TO.
CH— CH3 o — CH 2
CH— CH— cO — CO — CH3
— CH— CH,

a) 4- a) 2-
hexanone oxapentan-4-
b) 3- one b) 4-
rexona oxypentan-2-
c) 3- one c) 4-
hexanone oxapentan-2-
one d) N. TO.
7.
2. d) N.
CE,- TO.
CH = CH— CH 2
CE- CO — CE, OH — CHa
CHa CO—
a) 4- CH3 a) 5-
hexen-2-one oxo-2-
b) 2- pentanol b)
hexen-5-one 5-hydroxy-2-
c) 2- pentanone c)
penten-5- 1-hydroxy-4-
one pentanone d)
N. TO.
3. ,
C —
C
H
,
H
— —
C C
H H
— ,
—
C C
O O
— —
C C
H H
. ,
- 3
—
C -
H 3
, CH=CH 2
3
I
- a) 4-
ethenyl-2-
pentanone
3 b) 4-
CH,- methyl-5-
CH, hexen-2-one
c) 2-
ethenyl-4-
pentanone
d) N. TO.
a) 2-ethyl-
3-hexanone
b) 4-
methyl-3-
hexanone 5.
c) 3-
methyl-4-
hexanone CH-—
d) N. TO.
CH,— co —
CH,— C = CH
4.
C
H
- 160 - Nomenclature of Organic Chemistry

a) 1-hexin-
4-one a) ethyl
b) ethyl phenyl ketone
propenyl b) ethyl
ketone cyclohexyl
c) 5-hexin- ketone
3-one c) phenyl
d) N. TO. ethyl ketone
8. d) N. TO.
OHC—
CH,—CO—CH, 10.
—CHO

a) 3-
oxapentaned
ial b) 3-
oxopentaned a) cyclohex
ial c) 3- yl isopropyl
oxypentaned ketone
ial d) N. TO. b) phenyl
isopropyl
ketone
9. c) isopropyl
cyclohexyl
ketone d) N.
TO.
Nomenclature of Organic Chemistry - 161 -

Chap. 10

CARBOXYLIC ACIDS
CONTENT:

oefinition

Exercises
Functional
group
Formula
Questions
from_se^>
clo
Physical ailments

CARBOXYLIC
ACIDS
Import
System, ance

Becaus Aliphatic
e of
Comm
Greek on
alphabet Optici
ans
dey309
- 162 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We develop attitudes of responsibility in the investigation

of compounds carboxylic,
describing the variety fruits containing organic acids
natural and others produced
industrially, characteristic functional group, nomenclature
and its applications, to raise awareness of its importance in
regional production.

HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES

Excess uric acid in our blood causes it to concentrate in some places, such as the joints, forming urate
crystals that produce inflammation and cause pain. It commonly affects small joints such as the big toe or
fingers, although it can also occur in the joints of other bones. This problem is usually related to diet and high
levels of uric acid can lead to diseases such as gout.

First of all, you should eliminate certain foods from your diet that cause uric acid levels to rise, such as red
meat, tomatoes, alcoholic beverages, and carbonated drinks.

In the same way, it will be essential that you drink a lot of water to reduce uric acid, since it is through urine that
we eliminate this toxin from our body.

One of the natural remedies that you can use to reduce uric acid levels is the consumption of artichokes ,
since this vegetable has diuretic properties that will help uric acid be eliminated through urine. A good way to
take advantage of their benefits is to boil artichokes and, in addition to eating them, drink the broth resulting
from the boiling process.

Likewise, onion also helps to purify the body and thus prevent problems with uric acid. As in the previous case,
it is also recommended to boil onion water with the juice of a lemon and drink a couple of cups a day.

Apples will also be good allies in the fight against uric acid and, once again, apple water. You will have to boil
three chopped apples in one and a half liters of water for approximately half an hour.

On the other hand, the consumption of strawberries is also recommended to lower blood uric acid levels. You
can also choose to prepare an infusion from dried leaves or roots of the strawberry plant.
Nomenclature of Organic Chemistry - 163 -

Characteristics of carboxylic acids.- Organic acids carboxylic acids, because they have an acidic
and esters are widespread in nature, they are character . .
frequently found in fruits: citric acid in citrus fruits,
benzoic acid in green plums.

Lactic acid is found in animal tissues; methyl gallate

,0
in the leaves of various plant genera; Various organic
acids are found in spices.
–C
Short-chain organic acids, such as acetic, benzoic,
citric, propionic, and sorbic, are used as preservatives
or acidifiers.
–COOH
The simplest is methanoic acid (formic acid), followed
by ethanoic acid (acetic acid), which in a diluted and
impure state is part of vinegar. Carboxyl group

Many carboxylic acids are essential in the chemistry of Carboxylic acids are compounds that have the
living organisms. Others are chemicals of great carboxyl group (also called acid group) in their
industrial importance. structure.

The smell of vinegar is due to acetic acid; that of rancid To name them, the word acid is prefixed and then the
butter to butyric acid. Caproic acid is found in the hair chain is named with the prefix that indicates the
and secretions of goats. Acids C5 to C10 have “goat” number of carbons with the ending “ -oic ”.
odors.

All carboxylic acids are completely soluble in organic Functional group Formula
General name
solvents.

They are weak acids that are partially dissociated in

solution. The acidic character decreases with the
number of carbon atoms.
eithe R–COOH Carboxylic acid

r
ethanoic acid
As the size of the molecule increases, its tendency to Acetic acid
be greasy increases in such a way that the chemical
compounds of this group are acids, oils, fats and even
beeswax. CH 3 –
COOH of acids.- Depending on the type of
Classification
Uses of some acids: hydrocarbon radical attached to the functional group,
Formic Acid : Used as a preservative in the beer and Formula Names
wine industry. acids can be:
It is used in dyeing fabrics and in tanning. Aliphatic Aromatics

R – COOH Ar–COOH

Systematic nomenclature.- The IUPAC

nomenclature For carboxylic acids, use the name of
the alkane that corresponds to the longest continuous
chain of carbon atoms that includes the carboxyl
Acetic Acid (vinegar ): It is the most used. It is used group . The final o of the alkane name is replaced by
to prepare acetone, rayon, lacquer solvent and resins. the suffix oic and the word acid is prefixed.

Aspirin is formed with salicylic acid . The chain is numbered starting with the carboxyl
carbon atom to specify the positions of the substituents
Definition of carboxylic acids.- The combination of a along it. In naming, the carboxyl group takes
carbonyl group and another hydroxyl group on the precedence over any functional group.
same carbon atom is called a carboxyl group , so the
compounds that contain this group are called 1. It is not necessary to specify the position of the
- 164 - Nomenclature of Organic Chemistry

carboxyl group, since it occupies the end of the chain

(locator 1). 3-carboxyhexanedioic acid

When the chain contains two carboxyl functions, the – COOH –CH 2 –CH 2 –CH –CH 2 – COOH
dioic suffix is used. Yo
Examples: CH 2
H–COOH CH 3 – COOH Yo
COOH
methanoic acid ethanoic acid
3-(1-carboxymethyl)hexaodioic acid
COOH – COOH COOH – CH – COOH

H.O. OH H.O. OH
You can also name the compound with the ending
II II II II “tricarboxylic” , “tetracarboxylic” , etc. depending
EI EITHER EIT EITHER on the number of acid groups.
THER HER
ethanedioic acid propanedioic acid Examples:

1 23 4
2. Carboxylic acids can be compound, branched, and
COOH –CH 2 –CH –CH 2 –CH 2 – COOH
have double or triple bonds or both.
Yo
Examples: COOH

CH 3 –CH= CH – COOH 1,2,4-butane tricarboxylic acid

432I

2-butenoic acid COOH –CH 2 –CH–CH 2 –CH – COOH

COOH –CH 2 –CH –CH 2 –CH 2 – COOH Yo Yo

Yo COOH COOH

COOH
1,1,3,4-butane tetracarboxylic acid

COOH – CH = CH – COOH 2-methylbutenedioic acid

Yo
CH 3 CH 2 –CH 3

I
COOH–CH 2 – CH–CH = CH –CH 3

3-ethyl-4-pentenoic acid

3. When there are three or more groups ( -COOH ) in a compound, those that are not found in the terminal
carbons of the main chain are considered radicals and are designated with the carboxy prefix.

Examples:
Nomenclature of Organic Chemistry - 165 -

4. The acid function prevails in the nomenclature over

all those previously studied; Therefore, if the acid
function is found in a compound, the others are
considered substituents and the main function will be
that of the acid .

If the carbonyl group –CO– is found within the chain,

it is called oxo , as is the hydroxy group –OH.

Examples:

5432 1
CH –CH –CO –CH – COOH

3-oxopentanoic acid

54 32 1
CH – CHOH –CO –CH – COOH

4-hydroxy-3-oxopentanoic acid

54 3 2 1 Common nomenclature.- The IUPAC accepts the

CH –CH – CHOH –CH – COOH common names of many carboxylic acids, which are
frequently used in chemical language.
3-hydroxypentanoic acid
1. In most cases the name is due to its origin.
CHO–CH–CH–COOH Examples:

3-formylpropanoic acid Formula Common name

CH – CH – CH – CH – COOH I formic acid

H–COOH
CH–OH
acetic acid
3-hydroxymethylpentanoic acid CH 3 – COOH

propionic acid
CH 3 –CH 2 –COOH
COOH–CH –CH –CH – COOH I
COOH CH 3 –CH 2 –CH 2 –COOH butyric acid

2-carboxypentanedioic acid
CH 3 –(CH 2 ) 3 –COOH valerianic acid

5. When the acid group ( –COOH ) is attached to a oxalic acid

ring, the cycle is taken as the main chain and ends in a COOH – COOH
carboxylic acid.
malonic acid
Examples: COOH – CH – COOH

COOH –CH –CH – COOH succinic acid

glutaric acid
COOH – (CH 2 ) 3 – COOH
- 166 - Nomenclature of Organic Chemistry

2. Like aldehydes, the Greek alphabet is also used to

indicate the position of substituents. It begins with the
letter alpha ( ) from the second carbon that is next to
the carboxyl group (–COOH), the main chain goes with
the common name ending in ico.

Examples:

%BY
COOH –CH –CH 2 –CH 3
Yo
CH 3

methyl butyric acid

 Nomenclature of Organic Chemistry - 167 -

SPECIFIC HOLISTIC OBJECTIVE:....................2

DIAMOND.................................................4
Hybrid state.................................................5
Carbon atom with sp 3 hybridization...........5
h......................................................................8
ox....................................................................8
H%CxH...........................................................8
OX...................................................................8
h......................................................................8
saturated chain.............................................9
CH 3 –CH 2 –CH = CH 2................................9
Nomenclature 1979 Nomenclature 1993..9
Nomenclature 1979 Nomenclature 1993..9
CH 2 = CH–CH = CH 2.................................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name.................10
Systematic name trivial name.................10
Isomers are differentiated by the order in
which the atoms are bonded in the
molecule....................................................21
c) Isomerism of function : Different

1)
OH
5 4I 3 2 1
,°
OH

4-hydroxy-3-methylpentanoic acid

2)
Br
5 4
3 I 1st
5 32 1
II Yo
EITHEROH

2-bromo-5-oxopentanoic acid

3)
OO
II II
or OR

pentanedioic acid
 - 168 - Nomenclature of Organic Chemistry

functional group .......................................21

Huacaya X1 drilling rig (Chuquisaca)......23
SELF APPRAISAL :................................25
).................................................................25
SELF APPRAISAL : ORGANIC
CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:..................34
Characteristics of alkanes.- They are.....35
Example:...................................................35
Physical properties and uses of alkanes :. .35
3)...............................................................38
4)...............................................................38
5)...............................................................47
6)...............................................................47
8)...............................................................47
2,3,6–trimethylheptane (SI)......................47
10).............................................................47
11).............................................................48
Radicals or complex substituents.- They are
those substituents formed with primary and
secondary branches . To name them:........48
basic alkyl group ......................................48
3. HE name the branch followed
secondary..................................................48
Examples:..................................................48
12).............................................................48
n–nonyl either nonyl...............................49
Examples:..................................................49
isobutyl......................................................49
Examples:..................................................49
Examples:..................................................49
Examples:..................................................50
Examples:..................................................50
ter -pentil either........................................50
Incorrect: 3.4, 6,7,8...................................51
Name: 8-ethyl-4-isopropyl-3,5,7-
trimethyldecane.........................................51
Example:...................................................51
 Nomenclature of Organic Chemistry - 169 -

Solved exercises on branched alkanes.-....51

5)...............................................................52
Name:........................................................52
4)...............................................................52
2,3,5-trimethyl-4-propylheptane...............52
YO. Write the semi-developed and
topological formulas of the following
alkanes:......................................................54
1)...............................................................54
2)...............................................................54
3)...............................................................54
4)...............................................................54
5)...............................................................54
6)...............................................................54
8)...............................................................60
9)...............................................................60
10).............................................................60
SELF APPRAISAL : ALKANES (II)....72
SPECIFIC HOLISTIC OBJECTIVE:..................84
Physical properties and uses of alkynes :..85
In the common system , they are named as
derivatives of acetylene ............................85
Examples:..................................................85
Examples:..................................................85
Examples:..................................................86
2–pentine...................................................86
1–pentine...................................................86
1,3-butadiyne.............................................86
Acetylenic radicals or substituents.- They
are incomplete molecules of an alkyne:....87
Examples:..................................................87
Examples:..................................................87
Solved exercises on branched alkenes.-....87
5)...............................................................88
6)...............................................................88
PROPOSED EXERCISES........................91
YO. Write the semi-developed and
topological formulas of the following
 - 170 - Nomenclature of Organic Chemistry

alkynes:.....................................................91
II. There are errors in the following names
of alkynes, identify them, correct them and
write the correct name:..............................91
III. Write the semi-developed and
topological formulas of the following
alkenines:..................................................91
4)...............................................................93
5)...............................................................93
6)...............................................................93
ill...................................................................93
7)...............................................................93
9)...............................................................93
10).............................................................93
12).............................................................93
Yo..............................................................94
SELF APPRAISAL :................................95
SPECIFIC HOLISTIC OBJECTIVE:..................98
POLLUTION DUE TO HYDROCARBONS..98
1–cyclopropylbutane.................................99
Examples:..................................................99
Examples:..................................................99
Correct: 1, 1,3..........................................100
YO. Write the formula corresponding to the
following cycloalkanes:..........................103
CYCLIC HYDROCARBONS (I)...........105
SELF APPRAISAL :..............................106
CYCLIC HYDROCARBONS (II)..........106
5...............................................................106
wJCE..............................................................106
SPECIFIC HOLISTIC OBJECTIVE:................108
FOOD ALLIES TO MAINTAIN YOUR
WEIGHT........................................................108
Physical properties of aldehydes and
ketones :..................................................109
Examples:................................................113
Common nomenclature.- Aldehydes are
named in three ways :..............................113
Nomenclature of Organic Chemistry - 171 -

1. With their empirical names derived from

the corresponding carboxylic acids.........113
α-methyl- butyraldehyde.........................113
β-ethyl-γ-methyl -valeraldehyde.............113
Examples:................................................113
15)...........................................................114
16)...........................................................114
Aliphatic Aromatic Mixed....................115
Examples:................................................115
Examples:................................................116
4-methyl-3-penten-2-one........................116
Examples:................................................116
3-oxobutanal............................................116
2-oxobutanedial.......................................116
YO. Write the formula of the following
compounds:.............................................117
1).............................................................117
1...............................................................118
6...............................................................118
2...............................................................118
3...............................................................118
4...............................................................118
9...............................................................118
F..............................................................118
10.............................................................118
SELF APPRAISAL :..............................120
3...............................................................120
4...............................................................120
5...............................................................120
6...............................................................120
8...............................................................120
9...............................................................120
10.............................................................120
1...............................................................121
CH— CH— CH— cO— CH— CH,......121
7...............................................................121
2...............................................................121
 - 172 - Nomenclature of Organic Chemistry

3...............................................................121
4...............................................................121
5...............................................................121
8...............................................................121
9...............................................................121
10.............................................................121
CONTENT:........................................................122
SPECIFIC HOLISTIC OBJECTIVE:................123
HOW TO REDUCE URIC ACID WITH
NATURAL REMEDIES................................123
Carboxyl group.......................................124
Aliphatic Aromatics.............................124
CH 3 –CH= CH – COOH...........................125
2-butenoic acid........................................125
3-carboxyhexanedioic acid.....................125
3-(1-carboxymethyl)hexaodioic acid......125
Examples:................................................125
2-methylbutenedioic acid........................126
Examples:................................................126
3-oxopentanoic acid................................126
Examples:................................................127
CH 2 – COOH..............................................137
Some important carboxylic acids.-..........138
18)...........................................................138
YO. Write the formula of the compounds:
.................................................................139
II. Write the name of the compounds:.....139
1).............................................................139
2).............................................................139
3).............................................................139
4).............................................................139
5).............................................................139
6).............................................................139
7).............................................................139
8).............................................................139
9).............................................................139
10)...........................................................140
 Nomenclature of Organic Chemistry - 173 -

1).............................................................141
6).............................................................141
2).............................................................141
3).............................................................141
8...............................................................141
4).............................................................141
5).............................................................141
9).............................................................141
10)...........................................................141
1).............................................................142
6).............................................................142
2).............................................................142
CH-CH-CH-COOH.................................142
7).............................................................142
8).............................................................142
4).............................................................142
5).............................................................142
9).............................................................142
10)...........................................................142
SPECIFIC HOLISTIC OBJECTIVE:................144
USES OF ESTERS.........................................144
Characteristics of carboxylic acid
derivatives.- Esters.......They are compounds
.................................................................145
acid halide...............................................145
Ester........................................................145
Anhydride................................................145
Amide......................................................145
Nitrile......................................................145
acid + alcohol..........................................146
ester + water............................................146
The ester functional group is:..................146
R – COO –...............................................146
R – COO – R'..........................................146
Salt..........................................................146
ethanoate ion (acetate)...........................146
sodium ethanoate (sodium acetate).........146
- 174 - Nomenclature of Organic Chemistry

Names......................................................146
Ester........................................................146
Examples:................................................147
Examples:................................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate
.................................................................147
Examples:................................................147
( R – COO)X...........................................148
Solved exercises on esters and salts :......148
1).............................................................148
2).............................................................148
3).............................................................148
4).............................................................148
5).............................................................148
6).............................................................148
9).............................................................153
Examples:................................................155
Examples:................................................155
1).............................................................155
3).............................................................155
4).............................................................155
5).............................................................155
1) Write the formula of the following
compounds:.............................................156
1).............................................................158
6).............................................................158
7).............................................................158
either........................................................158
9).............................................................158
5).............................................................158
10)...........................................................158
1).............................................................159
6).............................................................159
2).............................................................159
3).............................................................159
7).............................................................159
8).............................................................159
 Nomenclature of Organic Chemistry - 175 -

4).............................................................159
5).............................................................159
9).............................................................159
10)...........................................................159
SPECIFIC HOLISTIC OBJECTIVE:................162
SODIUM CYANIDE.....................................162
Examples:................................................163
Aliphatic nitrile.......................................163
Examples:................................................163
Examples:................................................163
Various exercises solved on nitriles.-.....164
Examples:................................................164
cyclohexane carbonitrile.........................164
benzene carbonitrile................................164
Examples:................................................164
Examples:................................................164
R – NO 2.................................................166
Solved exercises on nitrocompounds.-....166
PROPOSED EXERCISES......................167
1. Write the formulas for:....................167
5...............................................................168
1...............................................................168
6...............................................................168
2...............................................................168
3...............................................................168
7...............................................................168
8...............................................................168
4...............................................................168
9...............................................................168
1...............................................................171
2...............................................................171
7...............................................................171
3...............................................................171
8...............................................................171
4...............................................................171
5...............................................................171
9...............................................................171
 - 176 - Nomenclature of Organic Chemistry

10.............................................................171
2...............................................................172
1...............................................................172
6...............................................................172
3...............................................................172
8...............................................................172
4...............................................................172
9...............................................................172
5...............................................................172
10.............................................................172
1...............................................................173
2...............................................................173
3...............................................................173
4...............................................................173
5...............................................................173
8...............................................................173
9...............................................................173
10.............................................................173
WEEBGRAPHY.....................................178

Yo
CH 3
a – ethyl – ft –methyl valerianic acid

3. Derived system.- They are also named as

derivatives of acetic acid , with the exception of formic
acid.

Examples:

CH 2 – COOH
Yo
CH 3

methyl acetic acid (propanoic acid)

CH 3 –CH 2 – CH – COOH
Yo
CH 3

ethyl methyl acetic acid (2-methylbutanoic acid)

Solved exercises on acids.- Check the following

 Nomenclature of Organic Chemistry - 177 -

examples:
- 178 - Nomenclature of Organic Chemistry

12) Some important carboxylic acids.-

Due to its application:
OH
Yo Acetic acid : It is the main ingredient in vinegar. Its
name is derived from the Latin acetum, which means
CHO –C –CH –C – COOH
sour. Known and used by humanity for quite some
Yo II time, it is used as a condiment and food preservative.
CH 3 EITHER
4-hydroxy-4-formyl-2-oxopentanoic acid
13)

CH 2 – COOH CH 3 –
Yo COOH
COOH – CH 2 –C –CH 2 –CH 2 – COOH
Yo
CH 2 – COOH
Acetylsalicylic acid : Known as aspirin and used
here 3,3-bis-(carboxymethyl)hexanedioic acid against fever and analgesic, it is produced together
with acetic acid, by the esterification reaction of
1 salicylic acid (2-hydroxybenzoic) with acetic
4 CH 2 anhydride. The name salicylic acid derives from the
) –CH 3 Latin for the willow tree, salix.
Yo
CH – CH –
CH –
COOH
2,3-
Yo
dimethylpenta
1
noic CH
acid3
5 OH
) Yo Citric acid : It is responsible for the acidity of citrus
CH –CH –CH –CH –CH fruits. For industrial use, citric acid is manufactured
– COOH by the aerobic fermentation of cane sugar (sucrose)
3- or corn sugar (dextrose) by a special strain of
hydroxyhex Aspergillus niger. Its greatest use is as an acidulant
1 anoic acid in carbonated drinks and foods.
6 1 3
) CH – 4
CH –
CO –
p–(3– CH COOH
1 oxobutyl)benzo Yo
7 ic acid COOH–CH 2 – COH–CH 2 – COOH
)

COOH –CH –CH –CH - Propionic acid : It is responsible for the

CH characteristic smell of Swiss cheese. During the main
– ripening period of this type of cheese,
CO Propionibacterium shermanii, and similar
3-carboxy-4-
1 phenylhexanedioic OH microorganisms, convert lactic acid and lactates to
acid I propionic, acetic acids and carbon dioxide. The
8 COOH gaseous CO 2 generated is responsible for the
NH2
) Yo formation of the “holes” characteristic of Swiss
CH 3 –CH 2 –CH – cheese.
CH
2 – CH 3 –CH 2 –COOH
CO
3-amino-3-
OH
hydroxypentanoic
acid I
OH
 Nomenclature of Organic Chemistry - 179 -

YO. Write the formula of the PROPOSED EXERCISES II. Write the name of the compounds:
compounds:
following 1)
1. 2,4-pentadienoic acid
CH –CH –CH – COOH
Yo
2. 2-penten-4-ynoic acid

3. 2-carboxy-3-methylhexanedioic acid CH – CH
2)
4. 3-oxopentanoic acid
CH
5. 5,5-dihydroxy-2-hexenoic acid Yo
6. Acetic acid CH – CH – C – COOH
Yo
7. 3-hydroxy-4-oxopentanoic acid CH

8. 2-carboxypentanedioic acid 3)

9. Formylpropanoic acid CH 3 –CH –CH

–CH –
10. butynedioic acid CO –
COOH I
11. 2-methyl-3-pentenoic acid Yo
CH3OH
12. 3-hydroxycyclohexanecarboxylic acid
4)
13. 2-hepten-5-yne-dioic acid
COOH – CH – CH – COOH
14. 5-bromo-2-methylpentanoic acid
5)
15. 3-ethylbutynedioic acid CH = CH – CH = CH – COOH
6)
16. 2-hydroxy-3-oxohexanoic acid
COOH – C – C – COOH
17. 2,5-octadienedioic acid II II
EITHER EITHER
18. 5-chloro-4-fluoro-3-oxopentanoic acid
7)
19. 2-methyl-3-pentenoic acid
Cl OH II
CH – CH – C – C – CH – COOH
20. 3-carboxypentanedioic acid
II
21. 2,5-diheptindioic acid CH CH
II CH
22. 2-ethylhex-3-enoic acid
8)
23. Cyclohex-3-enecarboxylic acid
CH C –CH –CH 3 –COOH I
24. 3-hydroxyhex-2-enoic acid

25. 3-cyclopentylpropanoic acid CH – CH

26. but-2-enedioic acid 9)

27. 2-formyl-4-hydroxy-3-oxohexanedioic acid CH I

CH – C – CH – COOH
28. 5-cyclopropyl-4-phenyl-3-isopropylheptanoic acid I CH
- 180 - Nomenclature of Organic Chemistry

10)

CH 3 –CH = C –CH 2 –COOH I

CH 2 I
CH 3
Nomenclature of Organic Chemistry - 181 -

SELF APPRAISAL : CARBOXYLIC ACIDS (I)

1) 6)
HOOC —CH—CH—CH —COO H
I2
COOH
a) butanoic acid b)
propanoic acid c) a) 1,2,5-pentanetricarboxylic acid
paranoic acid d) N. b) 1,1,3-propanetrioic acid
TO. c) 1,1,3-propanetricarboxylic acid
d) N. TO.

2)
7.

a) propanoic acid
b) acetic acid a) 2-hydroxypropanoic acid
c) propanedioic acid b) 2-hydroxypropanoic acid
d) N. TO. c) 2-hydroxyethanoic acid d)
N. TO.

3)
8.

a) butenoic acid b) a) 2-oxopentanoic acid b) 2-oxobutanoic acid c) 4-oxopentanoic acid d) N.

butanoic acid c) 2- TO.
butenoic acid d) N.
4) TO. benzenedicarboxylic acid c) o-benzenedicarboxylic
acid d) N. TO.

a) butanoic acid 10)

b) butanedioic acid c) 1,4-butanoic acid d) N. TO. HOOC— CH—COH— CH— COOH

COOH

5)
a) 3-hydroxy-1,3,5-pentanetricarboxylic acid
CH—CE=CH— CH — CO OH
b) 2-hydroxy-1,2,3-propanetricarboxylic acid
CB, c) 1,2,3-propanoltricarboxylic acid
d) N. TO.
a) 4-methyl-2-pentenoic acid
b) 2-methyl-3-pentenoic acid
c) 2-methyl-2-pentenoic acid
d) N. TO.
9)

a) p-benzenedicarboxylic acid b) m-
- 182 - Nomenclature of Organic Chemistry

SELF APPRAISAL : CARBOXYLIC ACIDS (II)

1) 6)
HOOC-CH=CE-COOH HOOC-CH-CH-CH-COOH

COOH COOH
a) 1,4-ethenedicarboxylic
acid
b) 1,2-ethenedicarboxylic a) 1,1,3,3-
acid pentanetetracarboxylic acid
c) 1,4-butenedicarboxylic b) 2,4-pentanetetracarboxylic
acid acid
d) NA c) 1,1,3,3-
propanetetracarboxylic acid d)
N. TO.
2) c) 3-methyl-1-pentenoic
HOOC- CH,— CH,-CH- acid
COOH d) N. TO.
7)
CH,—CH—CH,—COOH
a) propanedioic acid
b) swampdioic acid
CH,
c) pentanedioic acid
d) N. TO.
a) 3-methyl-butanoic acid
b) 2-methyl-butanoic acid
3) c) 2-isopropyl-ethanoic acid
CH-CH-CH-COOH d) N. TO.

CH=CH,
8)

a) 3-vinylbutanoic acid
b) 3-methyl-4-pentenoic
acid

4) acid b) 4-
CH= c — CH, —CH— cyclohexenecarboxylic acid c)
COOH - I - 1-cyclohexenecarboxylic acid
- d) N. TO.
EC,
a) o-cyclohexanedicarboxylic
acid b) 1,3-
a) 2-methyl-1-pentenoic cyclohexanedicarboxylic acid c)
acid p-cyclohexanedicarboxylic acid
b) 4-methylpentenoic acid d) N. TO.
c) 4-methyl-4-pentenoic
acid
d) N. TO. 9)
CH-— CHOH— CH,— CH,-
COOH
5)

a) 4-hydroxypentanoic acid
b) 2-hydroxypentanoic acid
c) 4-oxypentanedioic acid
a) 3-cyclohexenecarboxylic d) N. TO.
Nomenclature of Organic Chemistry - 183 -

10) d) N. TO.
CH, — CH— CO — CH,
— COOH

a) 3-oxapentaenoic acid
b) 3-carboxypentanoic
acid
c) 3-oxopentanoic acid
- 184 - Nomenclature of Organic Chemistry

Chap. 11

DERIVED FROM THE

CARBOXYLIC ACIDS

ESTERS HALIDE SALTS

ACID ANHYDRIDES
CONTENT:
Nomenclature of Organic Chemistry - 185 -

SPECIFIC HOLISTIC OBJECTIVE:

We value the productive vocation through research on the

derivatives of organic acids, describing the applications of
esters, salts, halides and anhydrides, to raise awareness of
their importance in regional production.

USES OF ESTERS
Esters produce the pleasant odors and flavors associated with many fruits and flowers. Once a fruit or flower
has been chemically analyzed the flavor chemicals can try to copy the smell or taste. They rarely achieve
complete success but it comes pretty close for practical purposes. Artificial fruit flavors are often a mixture of
esters, which is why they are used in the preparation of jellies, gelatins, etc.

The waxes produced by some animals and plants, including beeswax, which is used to make candles and
polishes, and carnauba wax, which is used to polish cars and floors, are esters of carboxylic acids.

Peppermint oil, or methyl salicylate, has a minty odor and flavor. It is used as a mint flavoring and skin
ointment, as it works to relieve irritation and produces heat that soothes sore or inflamed muscles.
- 186 - Nomenclature of Organic Chemistry

Characteristics of carboxylic acid derivatives.- flowers, fruits and essential oils .

Esters They are Classification of derivatives.- The most important
compounds derivatives of carboxylic acids are esters , amides
interesting to highlight for being widely distributed in and nitriles .
nature since they are found fulfilling important
functions in both animals and plants. Halides and anhydrides of acids are also included
in this group, although they are often considered as
In vegetables, they also contribute, due to their activated forms of the acids, rather than as different
pleasant odors, to the characteristic fragrance of compounds.
R– R –C–O –C –
Esters are used in many and varied fields of C–X R
commerce and industry, such as the following: II II II
EIT EITHER
a) Solvents : Low molecular weight esters are liquid HER
acid halide Anhy
EITHER
and are usually used as solvents, especially the
dride
acetates of methyl, ethyl and butyl alcohols.
R–C–O R–C–
– R' NH 2 R –CN
II II
b) Plasticizers : Cellulose acetatepropionate and EITHE EIT
cellulose acetatebutyrate have achieved great R HER
E Am Nit
importance as thermoplastic materials. st ide rile
c) Artificial flavors : Many of the low molecular Halogenicerradicals.- They result from the breaking of
weight esters have characteristic fruity odors: banana the carbon-hydroxide bond of the carboxyl group , to
(isoamyl acetate), rum (isobutyl propionate), and form carboxylate anions.
pineapple (butyl butyrate). These esters are used in
the manufacture of synthetic aromas and perfumes. To name them, the ico ending of the acid is changed
to ato or oato .

H–COOH
(H – COO) – + H+
methanoic acid
methanoate anion

Examples:

d) Food additives : These same low molecular

weight esters that have characteristic fruity odors are
used as food additives, for example, in candies and
other foods that must have a fruity flavor.

e) Pharmaceutical products : Products as frequently

used as pain relievers are manufactured with esters.

f) Insect repellents : All insect repellents that we can

find on the market contain esters.

Organic acid radicals.- They are incomplete

molecules of carboxylic acids that result from the
breaking of the bonds of the atoms of the carboxyl
group .

They are of two kinds: halogenic radicals and acyl

radicals.
Acid
Halogen radical
Nomenclature of Organic Chemistry - 187 -

H – COOH methanoic acid

H – COO –

metan oato formi ato

CH 3 – COOH ethanoic
CH 3 – COO –
acid
etan oate acet ate
- 188 - Nomenclature of Organic Chemistry

The difference between a salt and an ester lies

C 2 H 5 – COOH propanoic mainly in that the oxygen-metal bond ("O"Na) of a
salt is ionic , while the oxygen-alkyl radical bond
C 2 H 5 – COO –
acid ("O"CH 3 ) of an ester is covalent .
propane oato propion ato

COOH – COOH (COO – COO) =

Esters .- Esters are compounds that come from the
reaction of carboxylic acids with alcohol:
ethanedioic acid
ethanedi ato oxal ato
acid + alcohol ester + water
–COOH –COO –

In practice, esters result from the combination of the

benzoic acid benz oato halogenic radical with the alkyl radical.

The ester functional group is:

Formation of salts and esters.- If we replace the
hydrogen of the carboxyl group with a metal we R – COO –
obtain the salts of the carboxylic acids.
The general formula of esters:
Examples:
R – COO – R'
A S
n a Observe the following
i l table:
E
o
ITHER
t
n CH –O Formula
CH 3 – Functional group General name
O 3
O- EITHER EITHER
E Na II II ester
ITHER - –C –OR R –C –OR
sodium
ethano ethanoate F N
ate ion (sodium o
(acetat acetate)
O
CH 3 –CH 2 rE ames
e) 2 –
CH 3 –CH –C OK ITHEm
C R u
meth
EITHER - lI
I
a yl
propanoa CH –
propanoate te C –
Classification of esters.- Taking into account the
ion potassiu type of acid,OCH ethan
they can be: organic and inorganic .
m
If we replace the hydrogen of the carboxyl group According to the molecular structure:oatesaturated and
with alkyl radicals , esters are obtained . unsaturated .
meth
Examples: Nomenclature of esters.- Like the previous
compounds, they are named according yl to IUPAC
E standards. and common system.
A aceta
ni s
1. According to the IUPAC rules , the halogenic
o t O radical or anion is named first , tefollowed by the
CH 3 –CHe2 –C
EITHER
n preposition of ; then the alkyl or aromatic radical ( yl
CH 3 – r
O O– ending)
CH
EITHE 3

R-
ethanoat methyl
e ion ethanoate
(acetate (methyl
) acetate)
 Nomenclature of Organic Chemistry - 189 -

In the common system , the common name of the acid ending in ato
is used, followed by the radical with the ending yl.
Examples: If R' is the main group
the substituent R–COO– is named acyloxy– .
Formula Name Common The names alkoxycarbonyl or
IUPAC name aryloxycarbonyl are also used.

H – COO – CH 3 methyl methyl Examples:

methanoate formate
321
propyl propyl CH 3 –CH 2 –CH 2 –COO –CH 2 –CH 2 –
C 3 H 7 – COO – C 3 H 7 COOH
butanoate butyrate
3- butanoyloxypropanoic acid

2. Esters are priority groups over amines, CH 3 – COO – CH 2 – CH 2 – COOH

alcohols, ketones, aldehydes, nitriles, amides
and alkanoyl halides. These groups are
named as substituents with the ester being the
functional group. 3- methoxycarbonyl propanoic acid

Examples:

p– phenyloxycarbonyl benzoic acid

4 3 21 OH EITHER
Yo II CH 3 –COO –CH 2 –CH
CH 3 –CH–CH 2 –C –O –CH 3 –
COO –CH 3 I
methyl 3-hydroxybutanoate
COO – CH 3

2– dimethyl methoxycarbonyl butanedioate

OH EITHER Examples:
6 5 4 I2 3 II
CHO – 5 CH –CH–CH –CH – 1 C –O –CH –CH
Yo COOH –CH 2 –CH 2 –COO –CH 2 –CH 3
CH

3- ethoxycarbonyl propanoic acid

Ethyl 3-hydroxy-4-methyl-6-
oxohexanoate
4. When the ester group is attached to a
cycle, the cycle is named as the main chain
and the ending –alkylcarboxylate is used.
3. When the ester group is not the head
group, the name will depend on the radicals R Example:
or R' the head group.

If R is the main group the –COO– R'

substituent is named alkoxycarbonyl or
aryloxycarbonyl . (Carboxylic acids and
anhydrides have priority over esters)
 - 190 - Nomenclature of Organic Chemistry

(CH 3 – COO)Na sodium ethanoate sodium acetate

Solved exercises on esters and salts :

Check the following exercises:

1)

EITHER
Salts of organic acids.- The organic salt is II
generally the result of the chemical reaction CH 3 –C –O –CH 2 –CH 3
between an alkali (generally sodium or
ethyl ethanoate (ethyl acetate)
potassium hydroxide) and some fatty acid; This
2)
reaction is called saponification . The fatty
acid can be, for example, lard or coconut oil. Or II
H–C –O –CH 2 –CH 3
The organic salt is soluble in water and forms
ions, due to its properties it is a detergent .
ethyl methanoate (methyl formate)
In practice, organic salts result from the 3)
ionic combination of the halogenic radical C) –C –O –CH 2 –CH 3
with a metal.
EITHER
The general formula is: ethyl benzenecarboxylate
( R – COO)X 4)
CH 2 = CH –CH 2 –C –O –CH 3
Observe the following table: II
EITHER
Functional group Formula General methyl 3-butenoate
name 5)
EITHER EITHER CH 3
II II Salt Yo
R –C –O – R – C – O. X CH 3 –CH –C–O –CH 3
II
EITHER
Formula Names
methyl 2-methylpropanoate
EITHER potassium ethanoate
II
CH 3 –C –OK
potassium acetate

Nomenclature of organic salts.- According

to the IUPAC rules , the halogenic radical or
anion is named first , followed by the
preposition of ; below the name of the metal.

Examples:
Name
Formula Common name
IUPAC

(CH 3 – COO) 2 Pb lead(II) ethanoate lead(II) acetate

 Nomenclature of Organic Chemistry - 191 -

6)
SPECIFIC HOLISTIC OBJECTIVE:....................2
DIAMOND.................................................4
Hybrid state.................................................5
Carbon atom with sp 3 hybridization...........5
h......................................................................8
ox....................................................................8
H%CxH...........................................................8
OX...................................................................8
h......................................................................8
saturated chain.............................................9
CH 3 –CH 2 –CH = CH 2................................9
Nomenclature 1979 Nomenclature 1993..9
Nomenclature 1979 Nomenclature 1993..9
CH 2 = CH–CH = CH 2.................................10
Nomenclature 1979 Nomenclature 199310
Systematic name trivial name.................10
Systematic name trivial name.................10
Isomers are differentiated by the order in which the atoms are bonded in the
molecule....................................................21
c) Isomerism of function : Different functional group . 21
Huacaya X1 drilling rig (Chuquisaca)......23
SELF APPRAISAL :................................25
).................................................................25
SELF APPRAISAL : ORGANIC CHEMISTRY (II) 30
SPECIFIC HOLISTIC OBJECTIVE:..................34
Characteristics of alkanes.- They are.....35
Example:...................................................35
Physical properties and uses of alkanes :. .35
3)...............................................................38
4)...............................................................38
5)...............................................................47
6)...............................................................47
8)...............................................................47
2,3,6–trimethylheptane (SI)......................47
10).............................................................47
 - 192 - Nomenclature of Organic Chemistry

11).............................................................48
Radicals or complex substituents.- They are those substituents formed with primary
and secondary branches . To name them:. 48
basic alkyl group ......................................48
3. HE name the branch followed secondary 48
Examples:..................................................48
12).............................................................48
n–nonyl either nonyl...............................49
Examples:..................................................49
isobutyl......................................................49
Examples:..................................................49
Examples:..................................................49
Examples:..................................................50
Examples:..................................................50
ter -pentil either........................................50
Incorrect: 3.4, 6,7,8...................................51
Name: 8-ethyl-4-isopropyl-3,5,7-trimethyldecane 51
Example:...................................................51
Solved exercises on branched alkanes.-....51
5)...............................................................52
Name:........................................................52
4)...............................................................52
2,3,5-trimethyl-4-propylheptane...............52
YO. Write the semi-developed and topological formulas of the following alkanes:
...................................................................54
1)...............................................................54
2)...............................................................54
3)...............................................................54
4)...............................................................54
5)...............................................................54
6)...............................................................54
8)...............................................................60
9)...............................................................60
10).............................................................60
SELF APPRAISAL : ALKANES (II)....72
SPECIFIC HOLISTIC OBJECTIVE:..................84
Physical properties and uses of alkynes :..85
 Nomenclature of Organic Chemistry - 193 -

In the common system , they are named as derivatives of acetylene . 85

Examples:..................................................85
Examples:..................................................85
Examples:..................................................86
2–pentine...................................................86
1–pentine...................................................86
1,3-butadiyne.............................................86
Acetylenic radicals or substituents.- They are incomplete molecules of an alkyne:
...................................................................87
Examples:..................................................87
Examples:..................................................87
Solved exercises on branched alkenes.-....87
5)...............................................................88
6)...............................................................88
PROPOSED EXERCISES........................91
YO. Write the semi-developed and topological formulas of the following alkynes:
...................................................................91
II. There are errors in the following names of alkynes, identify them, correct them
and write the correct name:.......................91
III. Write the semi-developed and topological formulas of the following
alkenines:..................................................91
4)...............................................................93
5)...............................................................93
6)...............................................................93
ill...................................................................93
7)...............................................................93
9)...............................................................93
10).............................................................93
12).............................................................93
Yo..............................................................94
SELF APPRAISAL :................................95
SPECIFIC HOLISTIC OBJECTIVE:..................98
POLLUTION DUE TO HYDROCARBONS..98
1–cyclopropylbutane.................................99
Examples:..................................................99
Examples:..................................................99
Correct: 1, 1,3..........................................100
 - 194 - Nomenclature of Organic Chemistry

YO. Write the formula corresponding to the following cycloalkanes: 103

CYCLIC HYDROCARBONS (I)...........105
SELF APPRAISAL :..............................106
CYCLIC HYDROCARBONS (II)..........106
5...............................................................106
wJCE..............................................................106
SPECIFIC HOLISTIC OBJECTIVE:................108
FOOD ALLIES TO MAINTAIN YOUR WEIGHT 108
Physical properties of aldehydes and ketones : 109
Examples:................................................113
Common nomenclature.- Aldehydes are named in three ways : 113
1. With their empirical names derived from the corresponding carboxylic acids.
.................................................................113
α-methyl- butyraldehyde.........................113
β-ethyl-γ-methyl -valeraldehyde.............113
Examples:................................................113
15)...........................................................114
16)...........................................................114
Aliphatic Aromatic Mixed....................115
Examples:................................................115
Examples:................................................116
4-methyl-3-penten-2-one........................116
Examples:................................................116
3-oxobutanal............................................116
2-oxobutanedial.......................................116
YO. Write the formula of the following compounds: 117
1).............................................................117
1...............................................................118
6...............................................................118
2...............................................................118
3...............................................................118
4...............................................................118
9...............................................................118
F..............................................................118
10.............................................................118
SELF APPRAISAL :..............................120
3...............................................................120
 Nomenclature of Organic Chemistry - 195 -

4...............................................................120
5...............................................................120
6...............................................................120
8...............................................................120
9...............................................................120
10.............................................................120
1...............................................................121
CH— CH— CH— cO— CH— CH,......121
7...............................................................121
2...............................................................121
3...............................................................121
4...............................................................121
5...............................................................121
8...............................................................121
9...............................................................121
10.............................................................121
CONTENT:........................................................122
SPECIFIC HOLISTIC OBJECTIVE:................123
HOW TO REDUCE URIC ACID WITH NATURAL REMEDIES 123
Carboxyl group.......................................124
Aliphatic Aromatics.............................124
CH 3 –CH= CH – COOH...........................125
2-butenoic acid........................................125
3-carboxyhexanedioic acid.....................125
3-(1-carboxymethyl)hexaodioic acid......125
Examples:................................................125
2-methylbutenedioic acid........................126
Examples:................................................126
3-oxopentanoic acid................................126
Examples:................................................127
CH 2 – COOH..............................................137
Some important carboxylic acids.-..........138
18)...........................................................138
YO. Write the formula of the compounds:139
II. Write the name of the compounds:.....139
1).............................................................139
 - 196 - Nomenclature of Organic Chemistry

2).............................................................139
3).............................................................139
4).............................................................139
5).............................................................139
6).............................................................139
7).............................................................139
8).............................................................139
9).............................................................139
10)...........................................................140
1).............................................................141
6).............................................................141
2).............................................................141
3).............................................................141
8...............................................................141
4).............................................................141
5).............................................................141
9).............................................................141
10)...........................................................141
1).............................................................142
6).............................................................142
2).............................................................142
CH-CH-CH-COOH.................................142
7).............................................................142
8).............................................................142
4).............................................................142
5).............................................................142
9).............................................................142
10)...........................................................142
SPECIFIC HOLISTIC OBJECTIVE:................144
USES OF ESTERS.........................................144
Characteristics of carboxylic acid derivatives.- Esters They are compounds
.................................................................145
acid halide...............................................145
Ester........................................................145
Anhydride................................................145
Amide......................................................145
Nitrile......................................................145
Nomenclature of Organic Chemistry - 197 -

acid + alcohol..........................................146
ester + water............................................146
The ester functional group is:..................146
R – COO –...............................................146
R – COO – R'..........................................146
Salt..........................................................146
ethanoate ion (acetate)...........................146
sodium ethanoate (sodium acetate).........146
Names......................................................146
Ester........................................................146
Examples:................................................147
Examples:................................................147
Ethyl 3-hydroxy-4-methyl-6-oxohexanoate147
Examples:................................................147
( R – COO)X...........................................148
Solved exercises on esters and salts :......148
1).............................................................148
2).............................................................148
3).............................................................148
4).............................................................148
5).............................................................148
6).............................................................148
9).............................................................153
Examples:................................................155
Examples:................................................155
1).............................................................155
3).............................................................155
4).............................................................155
5).............................................................155
1) Write the formula of the following compounds: 156
1).............................................................158
6).............................................................158
7).............................................................158
either........................................................158
9).............................................................158
5).............................................................158
 - 198 - Nomenclature of Organic Chemistry

10)...........................................................158
1).............................................................159
6).............................................................159
2).............................................................159
3).............................................................159
7).............................................................159
8).............................................................159
4).............................................................159
5).............................................................159
9).............................................................159
10)...........................................................159
SPECIFIC HOLISTIC OBJECTIVE:................162
SODIUM CYANIDE.....................................162
Examples:................................................163
Aliphatic nitrile.......................................163
Examples:................................................163
Examples:................................................163
Various exercises solved on nitriles.-.....164
Examples:................................................164
cyclohexane carbonitrile.........................164
benzene carbonitrile................................164
Examples:................................................164
Examples:................................................164
R – NO 2.................................................166
Solved exercises on nitrocompounds.-....166
PROPOSED EXERCISES......................167
1. Write the formulas for:....................167
5...............................................................168
1...............................................................168
6...............................................................168
2...............................................................168
3...............................................................168
7...............................................................168
8...............................................................168
4...............................................................168
9...............................................................168
 Nomenclature of Organic Chemistry - 199 -

1...............................................................171
2...............................................................171
7...............................................................171
3...............................................................171
8...............................................................171
4...............................................................171
5...............................................................171
9...............................................................171
10.............................................................171
2...............................................................172
1...............................................................172
6...............................................................172
3...............................................................172
8...............................................................172
4...............................................................172
9...............................................................172
5...............................................................172
10.............................................................172
1...............................................................173
2...............................................................173
3...............................................................173
4...............................................................173
5...............................................................173
8...............................................................173
9...............................................................173
10.............................................................173
WEEBGRAPHY.....................................178

CH 3 –CH –CH 2 –COO –CH 3 I

OH

Methyl 3-hydroxybutanoic acid

7)
CH – CH – CH – COOK I
CH 3

Potassium 3-methylbutanoate
 - 200 - Nomenclature of Organic Chemistry

Examples:
Acyl radical IUPAC name Common name

H – CO – methanoyl formyl

CH 3 – CO – ethanoyl acetyl

– CO – CO – ethanedioyl oxalyl

–CO – benzoyl benzoyl

Acid halides.- Acid halides (acid halides) are

compounds that derive from carboxylic acids
where the –OH group of the carboxyl group is
Some examples of esters.- Some natural replaced by a halogen (F, Cl, Br, I), being the
essences owe their aroma to the presence of most important acyl chlorides.
esters:
The general formula is: R – CO – X

Essences Esters responsible for aroma Nomenclature.- To name acid halides , write
the halogen with the ending uro followed by
the preposition de and then the name of the
Apricot Ethyl and amyl butyrates. acyl radical (with the ending oilo ).
Cognac and
Ethyl heptanoate. Examples:
wine
Name
Raspberry Isobutyl formate and acetate. Formula Common name
IUPAC
Jasmine Benzyl acetate.
ethanolyl
CH 3 – CO – F acetyl fluoride
Isoamyl isovalerianate and ethyl fluoride
Apple
butyrate and propionate.
1 – CO – I
Ethyl formate, butyrate and
Peach benzoyl iodide benzoyl iodide
isovalerianate.
Orange Octyl acetate.

Pear Isoamyl acetate.

1. The longest chain that contains the
Methyl, ethyl, butyl and isoamyl functional group is taken as the main chain.
Pineapple
butyrates The lowest carbon numbering of the halide .
Amyl acetates, and isoamyl and
Banana For radicals derived from acids that are named
isoamyl isovalerianate.
by the suffix –carboxylic (those that come
Ron ethyl formate from rings ), the ending –carbonyl is used.
Ethyl butyrate and nonanoate and amyl
Roses
undecylate.
Grapes Ethyl formate and heptanoate.
Acyl radicals.- They result from the breaking
of the oxygen-hydrogen bond of the carboxyl
hydroxide group .

To name them, the ico ending of the acid is

changed to –yl or –oyl .
 Nomenclature of Organic Chemistry - 201 -

Examples 5) 6)
:
EITHER EITHER
II II
H –C – Cl CH 3 –C–Br
methanoyl chloride ethanoyl bromide
7) 8)
CH 3 –CH 2 –CO –F CH 3 –CO –Cl

propanoyl fluoride acetyl chloride

2. This functional group has priority over 3) 4)
amines, alcohols, aldehydes, ketones, nitriles (-co- – CO – CO –
and amides (which must be named as
substituents). Only carboxylic acids , cyclohexanecarbonyl
anhydrides and esters have priority over it. oxalyl or ethanedioyl

Examples:

OH OH Br
I
5 3 7 6 5
4 2 1 ,O
4 3
Yo I
2 1
CL EITHER
II Yo
EITHER Br

4-hydroxy-3- chloride 2-bromo-5- bromide

methylpentanoyl oxoheptanoyl

3. When the acyl halide function is not the

main one (carboxylic acid, anhydride, ester), it
is named halocarbonyl , with the
corresponding locator number.

Examples:
Cl ✓ ° OO
CO
Yo II 4 2
Br 3 1OH
6 54 32 1OH
6 II

EITHER
4- bromocarbonyl butanoic
5- chlorocarbonyl -4- acid
oxohexanoic acid

Solved exercises on acid halides :

1) 2)
CH 3 –CO – CH 3 –CH 2 –CH 2 –CO –

acetyl or ethanolyl butyryl or butanoyl

 - 202 - Nomenclature of Organic Chemistry

Organic anhydrides.- These organic

substances can be considered as the result of
the condensation of two carboxylic acid
molecules after losing a water molecule
between them.
Nomenclature.- Symmetrical acid anhydrides
are named by replacing the word acid with
anhydride.

Asymmetric acid anhydrides are named with

the word anhydride followed by each
component of the carboxylic acid in
alphabetical order (without the word acid).

Examples:

1)
EITHER EITHER
II II
CH 3 –CH 2 –C –O –C –CH 2 –CH 3

propanoic anhydride
3)
CH 3 – CO – O – OC – CH 3

ethanoic anhydride
4)
CH 3 –CH 2 –CO– O –OC–CH 2 –CH 3

propanoic anhydride
5)
oo

benzoic anhydride
Nomenclature of Organic Chemistry - 203 -

PROPOSED EXERCISES
1) Write the formula of the following compounds: 1)

2) ethyl ethanoate HCOOK

2)
3) sec-butyl ethanoate
NaOOC – COONa
4) ethyl propanoate 3)
(CH 3 –CH 2 –COO) 2 Ca
5) isobutyl propanoate

6) isopropyl butanoate 4)

7) isopropyl ethanoate CH 3 –C ≡ C –COO Li

5)
8) tert-butyl ethanoate
CH 3 –COO–CH 3
9) isopropyl propanoate 6)

10) ethyl butanoate CH 3 –CH 2 –COO–CH 3

7)
11) isobutyl butanoate
HCOO –(CH ) –CH
12) Methyl 2-methyl-3-pentynoate 8)

13) propyl 3-pentenoate CH 3 –C ≡ C – COOK

9)
14) 2,3-dihydroxy-4-methylpentanoic acid
CH 3 –CH 2 –COONa
15) ethyl 2-propyl-3-hexenoate 10)

16) Isopropyl 3-ethoxy-4-hexinoate CH 3 –COO–CH 2 –CH 2 –CH 3

11)
17) sodium 2-hydroxybenzoate

18) 2-chloro-4,5-dimethyl-4-hexenoate © –COO Na

12)
19) 4-oxo-2-hexinedioic acid

20) Dimethyl 4,5-dihydroxy-2-hexinedioate (© –COO NH

13)
21) butyl 2,2-dichloroethanoate
CH 3 –COO–CH 2 –CH 2 –CH 2 –CH 3
22) 3,3-dimethyl-2,5-dioxoheptanoic acid 14)
23) phenyl 2,3-dichlorobutanoate CH 3 –CH 2 –CH 2 –COO–CH 3
15)
24) Potassium 3,5-dihydroxybenzoate
CH 3 –CH 2 –CH 2 –CH 2 –COOK
25) 2-bromo-3-ethoxybenzoic acid 16)

26) ammonium 2-chloro-6-hydroxybenzoate CH 3 –COO – (CH 2 ) –CH

17)
27) sodium 3-methoxypentanoate
CH –CH –COO –(CH ) –CH
28) methyl valerianate 18)

29) phenyl propionate CH 3 –CH 2 –OOC –COO –CH 2 –CH 3

II. Write the name of the following formulas:

- 204 - Nomenclature of Organic Chemistry

III. Write the name corresponding to the following

compounds and convert them to the formulas of
the semi-developed system:

1)

EITHER

EITHER
2)

EITHER
EITHER
3)
, either
Br Yo Yo
OH EITHER

4)

°
II Yo
OO

5)
Or II

EITHER

6)

OH EITHER

7)

EITHER
Nomenclature of Organic Chemistry - 205 -

EITHER
8)
EITHER
II
–O
©
9)

EITHER

-
10)

°s

H 7 0/
(

11)
EITHER

°
12)

O –O II

()
13)

either- EITHER

14)

EITHER
°-

15)

EITHER
either-

16)
O –O II

()
- 206 - Nomenclature of Organic Chemistry

17)

0
)—(
CL
Nomenclature of Organic Chemistry - 207 -

SELF APPRAISAL : ESTERS (I)

1) 6)

a) methyl ethanoate b) a) phenyl ethanoate

methyl methanoate c) b) phenyl propanoate
ethyl methanoate d) NA c) phenyl patronage
d) NA

2) 7)
either
CHECH—CH—c
Bo-CH,

a) ethyl ethanoate a) methyl 1-butenoate

b) ethyl methanoate b) methyl 3-butenoate
c) propyl methanoate c) methyl 3-propenoate
d) NA d) NA

3) 8)
CH—coo—CH,

a) ethyl ethanoate
b) methyl methanoate
c) methyl ethanoate a) isopropyl isobutylate b) isopropyl isopentylate c)
d) NA secpropyl isobutylate d) NA
4)
CH—coo—CH,
9)
a) methyl benzoate
b) phenyl ethanoate
c) ethyl benzoate
d) NA

a) Isobutyl 3-pentynoate
5) b) Isobutyl 2-pentenoate
c) Isobutyl 3-pentenoate NA
d)

a) methyl benzoate b)
10)
phenyl ethanoate c)
ethyl benzoate
d) NA

a) 3-butenoate of 2-propynyl
b) 1-butenoate of 2-propynyl
c) 1-butenoate of 1-propynyl
d) NA
 - 208 - Nomenclature of Organic Chemistry

SELF APPRAISAL : ESTERS (II)

1) 6)

a) methyl propanoate a) phenyl propanoate

b) butyl methanoate b) phenyl ethanoate c) benzyl propanoate d) NA
c) methyl butanoate NA
2) d) 7)
CHHO-CH- CH,—COO—CH,

a) methyl 4-oxapentanoate
b) methyl 4-hydroxypentanoate
a) isobutyl ethanoate c) methyl 4-oxypentanoate
b) isobutyl propanoate d) NA
c) propyl isobutylate NA
d)
8)
CH 2 OH— CH,— COO — CH,- CH,
3)

a) ethyl hydroxypropanoate
b) ethyl 3-hydroxy-propanoate
c) ethyl 1-hydroxy-propanoate
d) NA
a) Cyclohexyl 3-methyl-butanoate 9)
b) phenyl 3-methyl-butanoate HOOC—CH,—CH,—COO—CH,
c) cyclohexyl isobutanoate
d) NA a) 1-methoxycarbonyl-propanoic acid
b) 3-ethoxycarbonyl-propanoic acid c) 3-
methoxycarbonyl-propanoic acid d) NA
4)
CE = CH — CE- COO - CE,
10)
OHC — CH,- COO — CH,- CH,
a) methyl 3-butenoate
b) methyl 3-butanoate
c) methyl 1-butenoate a) ethyl 1-formyl acetate
d) NA b) ethyl 1-formyl-propanoate
c) ethyl 2-formyl acetate
d) NA
5)

a) methyl 3-benzyl propanoate b) methyl 3-phenyl propanoate c) methyl 1-phenyl propanoate d) NA

Nomenclature of Organic Chemistry - 209 -

Chap. 13

ORGANIC COMPOUNDS
NITROGENATED

NITRILES AND
NITROCOMPOUNDS

CONTENT:
 - 210 - Nomenclature of Organic Chemistry

SPECIFIC HOLISTIC OBJECTIVE:

We strengthen the care that must be taken when handling

explosive and toxic substances, through the study of organic
nitrogen compounds, describing the importance of nitriles and
nitro compounds, the characteristic functional group, the
nomenclature and their applications, and that allow us to
contribute to the well-being of the family environment.

SODIUM CYANIDE

Sodium cyanide is a chemical substance with the formula NaCN. It is a solid, inorganic compound. Physically it is a
poisonous, deliquescent crystalline white solid, commonly called white cyanide and also known as sodium
prussiate.

It is soluble in water, its aqueous solutions are very alkaline, with great reactivity with metals, especially gold, and
they decompose quickly.

Sodium cyanide itself is not combustible, but contact with acids can release highly flammable hydrogen cyanide
gases, which in the presence of combustion can generate irritating or poisonous gases.

Sodium cyanide is generally obtained from the treatment of “hydrogen cyanide” (HCN) with “sodium hydroxide”
(NaOH), producing “Sodium Cyanide” (NaCN) with water (H 2 O).

The water is removed by drying and filtering and the sodium cyanide is converted into white, solid briquettes of
approximately 10 square centimeters in the form of solid salts that are maintained in their state at controlled
temperatures and humidities, so the briquettes are placed in Labeled and sealed containers to protect them from
being crushed and damp.

Because the salt of sodium cyanide is derived from a weak acid, NaCN reverts to HCN by hydrolysis (very weakly
and slowly if dissolved in water and reacts very quickly with strong acids such as nitric acids, nitrates, nitrites and
fluorine).

Its main use is in the recovery of precious metals. Cyanide in dilute solutions and in the presence of oxygen
dissolves gold from minerals, forming sodium dicyanoaurate(I) , NaAu(CN) 2 Sodium cyanide is also used,
although on a small scale, in the synthesis of other products such as dyes (including optical brighteners), pigments
(Prussian blue), agrochemicals, pharmaceuticals, chelating or sequestering reagents (sodium nitrilotriacetate,
SNTA) and other specialties such as nitriles, isonitriles, heavy metal cyanides and glucoheptonate (from dextrose
hydrate and sodium cyanide in aqueous solution).
 Nomenclature of Organic Chemistry - 211 -

Characteristics of nitriles.- Nitriles have several cyanide , by replacing a hydrogen with an alkyl or aryl
uses among which are: radical.

Manufacture of synthetic latex which is used in the They are characterized by having the " cyano "
production of gloves. functional group ( –C ≡ N ), which is why they are
sometimes also called alkyl cyanides .
The male condom is generally made of latex while the
female condom is made of nitrile , so people allergic The general formula is: R – C Ξ N
to latex can use it without any problems.
Examples:
It is used in the production of dyes, for the chemical
Aliphatic nitrile

CH – CH –CN

ethyl cyanide
aromatic nitrile
and pharmaceutical industries. Nomenclature.- The
nomenclature of nitriles is
For the production of enamels and paints, cleaning
derived from the
products for industrial use.
corresponding carboxylic phenyl cyanide
Potassium cyanide : White powder, granular, acids.
hygroscopic; faint smell of bitter almonds.
Systematic nomenclature.- According to IUPAC
Dangers: It is extremely poisonous: by ingestion, by standards They are named according to the following
absorption through the skin, or by inhalation of possibilities:
hydrogen cyanide gas released by the action of carbon
dioxide or acids on potassium cyanide. Exposure to 1. Add the suffix –nitrile to the name of the
hydrogen cyanide gas is fatal within minutes at hydrocarbon with the same number of carbon atoms.
concentrations of 300 parts per million.
Examples:
Common uses: Similar to those of sodium cyanide: in
galvanizing, hardening of metal surfaces; organic and CH 3 –CH 2 –CN NC –CH 2 –CH 2 –CN
inorganic synthesis; extraction of gold and silver from
their minerals; as a fumigant for citrus and other fruit
propane nitrile butanedi nitrile
trees.

Sodium cyanide : colorless granules,

hygroscopic, with a weak odor of bitter almonds b) When the chain has substituents, they are listed
(hydrogen cyanide). based on the functional group and named in
alphabetical order.
Dangers: It is extremely toxic. It can poison by skin
absorption, by ingestion, or by inhalation of hydrogen Examples:
cyanide gas released by the action of acids or carbon
dioxide on sodium cyanide. It causes weakness,
CH 3 –CH –CH 2 –CH 2 –CNI
heaviness in the arms and legs, breathing difficulties,
headache, dizziness, nausea and vomiting, which are
sometimes followed by paleness, fainting, respiratory CH 3
collapse and death. Sodium cyanide, mixed with acids,
generates hydrogen cyanide gas, which is fatal within
minutes at concentrations as low as 300 parts per 4–methylpentane nitrile
million.

Common uses: Extraction of gold and silver from their

minerals; fumigation of citrus and other fruit trees.

Nitriles or Cyanides.- Nitriles can be considered

derivatives of hydrogen cyanide or hydrogen
- 212 - Nomenclature of Organic Chemistry

12 3 4 5 67
CH 3 – C ≡ N C 5 H 11 – C ≡ N "Oc"
N C –CH –CH –CH –CH –CH –CH
Yo Yo Yo
CHO O CH
methyl cyanide pentyl cyanide phenyl cyanide
I CH

ethane nitrile benzo nitrile

4-ethoxy-3-formyl-6-methyleptane nitrile non- nitrile hexa
aceto nitrile

3. When the group –C ≡ H is attached to a ring or Various exercises solved on nitriles.-

cycle; or when there are more than two functional Check the following examples:
groups, they are named with the suffix carbonitrile.
1) 2)
Examples H–C N CH – CH – C C – CN
:

N nitrile methane 2-pentynitrile

(Hydrogen cyanide ) (1-butynyl cyanide)

cyclohexane benzene
carbonitrile carbonitrile 3) 4)
CN –CH –CH –CN I C.N.
Yo Yo
4. When there are other functions that have priority
C.N. C.N. CH – C – COOH
over the –CN group, this is cited using the prefix
cyano– Yo
1,1,2,2–ethanetetra CH
Examples carbonitrile
:
2-cyano-2-
5 4321 methylpropanoic acid
CH – CH – CO – CH – COOH 5) 6)
Yo Yo
CN –CH –CH –CN CH – CH – C N
c CH
III Yo Yo Yo Yo
C.N. C.N.
N CH CH

1,1,2,2–
4-cyano-2-ethyl-3-oxopentanoic acid 2–methylpropane nitrile
ethanetetracarbonitrile
6 54 32
1 (isopropyl cyanide )
CH –CH – CHOH –CH –CH – COOH
Yo Yo 7) 8)
N.H. EITHER C.N.
Yo Yo CH –CH –CH –C N
C3H7 CH 3 –C – COOH Yo
Yo CH
CH 3
3-methylbutanenitrile
2-cyano-2-
Common nomenclature.- It is named starting with
methylpropanoic acid
the word cyanide followed by the name of the radical.
9)
Also eliminating the word acid and changing the oic
CH – CH – CH – CH – COOH I
ending of the common name of the acid to nitrile .
C.N.
3-cyanopentanoic acid
Examples
:
Nomenclature of Organic Chemistry - 213 -

10) 20) 21)

CH 3 –CH –CO –CH 2 –CH 2 –CH 3 I N
C.N. III (EITHER-*
_0,
II
EITHER
benzonitrile
2-cyano-3-hexanone (feline cyanide)
5-cyanopentanoic acid

11)
CN – CH – CH – CH – CH – CN I Yo 22) 23)
C.N. C.N. N III C CL
Yo

1,1,3,4–butanetetra carbonitrile
C.N.

12) carbonitrile
CH –CH = CH –CH –CH –CN cyclopentanecarbonitrile
24) 25)
4–hexenenitrile TO-.
NC
(3-pentenyl cyanide) ( )–COO –CH 2 –CH
3
cyclopropane carbonitrile
13)
21 ethyl 3-cyanocyclohexane
N C –CH –COO –CH –CH
carboxylate

ethyl cyanoacetate 26) 27)

C.N.
14) 15) -N

N „%
phenylethanenitrile 1-cyclohexen-1-
ethanenitrile carbonitrile
pentanenitrile
16) 17) 28) 29)
C.N. OH
K=N
65432 31 I 5

propanenitrile I 1 1 CN
NC "CH
2,4-dimethylhexanenitrile
3-cyclohexen-1-carbonitrile
18) 19) 3- cyano-5-methylphenol
N
III
•4 butanedinitril
30)

51I
CH
3
31)

31 I
C.N.
5

2-ethylpentanenitrile
H.O. C.N. HO 2 CH

3-cyano-5-hydroxytoluene 3-hydroxy-5-
methylbenzonitrile

Nitrocompounds.- They can be considered

- 214 - Nomenclature of Organic Chemistry

derivatives of hydrocarbons in which one or more

hydrogens were substituted by the nitro group: (– NO
2 )

The structure of nitro compounds is as follows:

R – NO 2

Nomenclature.- They are named by placing the prefix

– nitro indicating the position it occupies within the
main chain when necessary, in front of the name of the
corresponding alkane:

Examples:
CH – CH – CH – CH
Yo Yo
NO CH
CH – NO

nitromethane 3-methyl-2-nitrobutane

Unsaturations have preference over the nitro group:

Examples:

CH = CH – CH – NO

3–nitro–1–propene

CH 2 = CH–C C –CH 2 –CH –CH –NO 2

Yo
CH 3
6-methyl-7-nitro-1-hepten-3-yne

Solved exercises on nitrocompounds.-

Check the following examples:

1) 2)
CH 3 –NO 2 CH 3 –CH 2 –NO 2

nitromethane nitroethane

3) 4)

ON – -NO
CH 3 –CH 2 –CH 2 –NO 2
Nomenclature of Organic Chemistry - 215 -

1,4-dinitrobenzene

(p–dinitrobenzene)
5) 6)
CH 3 –CH –CH 3 I CH – CH – CH – CH I Yo
NO 2 NO NO

2–nitropropane 2,3-dinitrobutane

7) 8)
CH= CH – NO 2
CH 3 –< CH 2 = C–CH 2 –NO 2 I
Yo
CH 3
H3
c
2-methyl-3-nitropropene
–1–nitropropene
2–
methyl
9)
N 10)
O 2 CH I
TI CO I

nitrocyclohexane NO

m–nitroacetophenone

11) 12)
NO CHO
3I
or 1 2

3–nitrocyclohexene NO NO

3,5–dinitrobenzaldehyde

13) 14)
OH CH – O – NO
O2N II NO 2 Yo
CH – O – NO
Yo
CH – O – NO
NO
trinitrophenol glyceride trinitrate
(nitroglycerin)
- 216 - Nomenclature of Organic Chemistry

PROPOSED
EXERCISES

1. Write the formulas for:

1) methanonitrile

2) benzonitrile

3) cyclohexanecarbonitrile

4) propaneditrile

5) but-3-enenitrile

6) 3-oxocyclopentanecarbonitrile

7) butanedinitril

8) phenyl cyanide

9) 2-cyano-3-pentenoic acid

10) 1-butynyl cyanide

11) propenenitrile

12) 2,3-dimethyl-6-nitroaniline

13) 2-pentynitrile

14) 1,3-dinitrobenzene

15) 2-methyl-3-nitropropane

16) 2,4,6-trinitrotoluene

17) 3-methyl-4-pentinonitrile

18) 3-hexenenitrile

19) 5-nitro-1,3-cyclopentadiene

20) 4-nitro-1-pentene

21) 3-cyanobutanoic acid

22) Ethanedinitrile (cyanogen)

23) 2-methylpentanenitrile

24) 2-methylpropanenitrile

25) cyclopentanecarbonitrile

26) cyclopropanecarbonitrile

27) methyl 3-cyano-5-hydroxypentanoate

28) 4-ethyl-3-methyl-1,2-dinitro-2,4-hexadiene
Nomenclature of Organic Chemistry - 217 -

SELF APPRAISAL : NITRILES (I)

1. 6.
CH 3 –CN CH –CH –CH –CN I
Yo
CN CN
a) ethanenitrile
b) methanonitrile
c) ethyl cyanide a) 1,1,2,2-butanetetracarbonitrile
d) N. TO. b) 2,2,3,3-butanetetracarbonitrile
c) 1,1,2,2-ethanetetracarbonitrile
e) NA
2.
CH – CH – CH – CN
7.
CH – CH – CH – CN
a) butyl cyanide
b) propanenitrile Yo
c) propyl cyanide CH – CH
d) N. TO.
a) pentyl cyanide
b) 3-pentanecarbonitrile
c) 2-ethylpropanenitrile
3.
d) N. TO.
CH – CH = CH – CN

8.
a) 1-propenenitrile
b) 2-butenenitrile –CN
c) 2-propenenitrile
d) N. TO.
a) cyclohexanecarbonitril
e
4. b) phenylcarbonitrile
c) benzylcarbonitrile
CH = CH – CN
d) N. TO.

a) ethyl cyanide 9.
b) 2-propenenitrile
c) 1-propenenitrile –CN
d) N. TO.

5. a) benzylcarbonitrile
CH – CH –CH –CNI b) cyclohexanecarbonitril
CH e
c) phenyl cyanide
d) N. TO.
a) 3-methylbutanenitrile
b) 2-methylbutanenitrile 10.
c) 2-methylpropanenitrile
d) N. TO. C.N
.

a) CH
2-
met
hyl
ben
zen
eca
- 218 - Nomenclature of Organic Chemistry

rbo
nitri
le
b)
tolu
ene
cya
nid
e
c)
1-
met
hyl
ben
zen
eca
rbo
nitri
le
d)
N.
TO.
Nomenclature of Organic Chemistry - 219 -

SELF APPRAISAL : NITRILES (II)

1.
6.
CH 3 –CH 2 –CN CH 3 –CH 2 –CC –CH 2 –CN
a) ethanenitrile
b) propanenitrile
a) 3-
c) propanecarbonitrile
hexynecarbonitrile
d) N. TO.
b) 1-cyano-2-pentine
c) 3-hexinonitrile
d) N. TO.
2.
CH 3 –CH = CH –CH 2 –CN 7.
NC
a) 2-butenenitrile
b) 2-pentenenitrile
c) 3-pentenenitrile
d) N. TO. a) 1,4-cyclohexanedicarbonitrile
b) o-cyclohexanedicarbonitrile
c) m-cyclohexanedicarbonitrile
3. d) N. TO.
CH 3 –CH –CH 2 –CN
I 8.
CH 3
CH

a) isopentanenitrile
b) isobutanitrile c)
secpentanenitrile C.
d) N. TO. N.
a) 3-
methylbenzocarbonitrile
4.
b) 3-methylbenzonitrile
CH 3 –CH 2 –CH –CN c) 3-methylbenzenenitrile
I d) N. TO.
CH 3 –CH 2 –CH 2
9.
a) 3-hexanecarbonitrile CH 3 –CH 2 –CH –CH 2 – COOH
b) 3-propylbutanenitrile I
c) 2-ethyl- C.N.
pentanecarbonitrile
d) N. TO. a) 3-nitrilopentanoic acid
b) 3-cyanuropentanoic acid
5.
c) 3-cyanopentanoic acid
NC –CH –CH –CH –CN I d) N. TO.
C.N.

10.
a) 3-pentanecarbonitrile
b) 1,2,3-propanetricarbonitrile NC –CH 2 –CH 2 –CH –CH 3
c) 1,2,3-propanetricarbonyl I
d) N. TO. CHO

a) 4-formyl-pentanecarbonitrile
b) 4-cyano-2-methylbutanal
c) 4-formyl-pentanenitrile
d) N. TO.
- 220 - Nomenclature of Organic Chemistry

SELF APPRAISAL : NITROCOMPOUNDS (I)

1. 6.
CH 3 –CH 2 –NO 2 CH 3 –CH–CH 2 –CH 3
I
a) 1-nitroethane NO 2
b) 2-nitroethane a) 1-methylnitropropane
c) nitroethane b) nitrobutane
d) N. TO. c) 2-nitrobutane
d) N. TO.
2.
CH 3 –CH 2 –CH 2 –CH 2 –NO 2 7.
NO
a) 1-nitropropane 2
b) 1-nitrobutane
c) nitrobutane a) nitrocyclopentane
d) N. TO. b) 1-
3. nitrocyclopentane
CH 2 = CH–CH 2 –NO 2 8. c) nitrocyclopropane
d) N. TO.
a) 3-nitro-1-propene NO
2
b) 1-nitro-2-propene
c) 1-nitro-3-propene
d) N. TO. a) nitrobenzyl b)
nitrophenyl c)
nitrobenzene d)
4. N. TO.
CH 3 –CH= CH –NO 2
9.
a) 3-nitro-2-propene
b) 1-nitro-1-propene NO
c) 3-nitro-1-propene
d) N. TO.
a) p-chloronitrobenzene
b) m-
5. chloronitrobenzene c)
o-chloronitrobenzene d)
CH 3 –CH–NO 2
N. TO.
Yo
CH 3 10.
a) methylnitroethane b) 2-nitropropane c) 1-nitropropane NO
d) N. TO.
CH
NO
a)
2,4
,6-
trin
itro
be
nz
en
e
(T
NB
Nomenclature of Organic Chemistry - 221 -

)
b)
2,4
,6-
trin
itro
tol
ue
ne
(T
NT
)
c)
2,4
,6-
trin
itro
trol
en
e
(T
NT
)
d)
N.
TO
.
- 222 - Nomenclature of Organic Chemistry

SELF APPRAISAL : NITROCOMPOUNDS (II)

1. 6. d) N. TO.
CH – NO CH C – CH – NO

a) nitromethyl a) 1-nitro-2-propyne
b) methyl nitrate b) nitropropine
c) nitromethane c) 3-nitro-1-propyne
d) N. TO.

2. 7.
CH – CH – CH – NO ON NO

a) 3-nitropropane
b) 1-nitropropane 5.
c) 1-nitropentane
CH 3 –O –CH 2 –CH 2 –NO 2
d) N. TO.
a) 1,3-dinitrocyclohexane b) 1,5-
dinitrocyclohexane c) p-dinitrocyclohexane d)
3. N. TO.

CH – CH = CH – NO
8.
a) 1-nitropropene a) o-nitrotoluene b) p-nitrotoluene c) m-
b) 3-nitropropene nitrotoluene d) N. TO.
c) 3-nitro-2-propene
d) N. TO.
9.
CH – CH – CH – NO I
4. CH 3
CH – CH – CH – CH – CH I Yo
NO NO a) nitroisopropane
b) nitroisobutane
a) 2,4-dinitropentane c) nitro-2-methylpropane
b) 1,3-dimethyl-1,3-dinitropropane d) N. TO.
c) 1,3-dimethyldinitropropane
d) N. TO.
10. a) methoxynitroethane
b) nitroethyl methyl O 2 N –CH 2 –CH –CH 2 – NO 2 I
ether c) 2-nitroethyl CH
methyl ether d) N. TO.
a) dinitromethylpropane
b) dinitroisobutane
c) 1,3-dinitro-2-methylpropane
d) N. TO.

1) 1,3-butadiene 2) propane
CH

ON
 Nomenclature of Organic Chemistry - 223 -

ORDER OF PREFERENCE TO NAME AN ORGANIC COMPOUND

Sometimes it happens that several functions participate at the same time in the same compound, which is why
they are called polyfunctional substances .

In these cases, the following order of priority that the functional groups have to be named must be taken into
account:

Acids > Esters > Amides = Salts > Nitriles > Aldehydes > Ketones

> Alcohols > Amines > Ethers > Unsaturations > Saturated hydrocarbons

ORGANIC FUNCTIONS IN ORDER OF PRECEDENCE

TERMINATION AS A SUBSTITUTE
NAME FORMULA
(When it is the main (When it is a radical)
function)
Ac. carboxylic R – COOH -oico carboxy-
Ester R – COO – R' -oato oxycarbonyl-
Amide R – CO – NH 2 -amide carbamoyl-
Nitrile R–C≡N -nitrile cyano-
Aldehyde R – CHO -to the formil-
Ketone R – CO – R' -one oxo-
Alcohol R –OH -ol hydroxy-
Phenol Ar –OH -ol hydroxy-
Amine R – NH 2 -amine Not me-
Ether R – O – R' -oxy- oxy-, oxa-
double bond R = R' -eno ...enil-
Triple bond R ≡ R' -ino ...inil-
fluor-, chloro-, bromo-,
Halogen R –X
iodine
Nitroderivatives R – NO 2 nitro-
Alkyl radical R – R' -year ...il-
- 224 - Nomenclature of Organic Chemistry

4TA. BOLIVIAN PLURINATIONAL STUDENT SCIENTIFIC OLYMPIAD

20va. BOLIVIAN CHEMISTRY OLYMPIAD
23. Stage (Simultaneous

gQuMPAPa
Examination)

ETUOlANT PATERNAL
SURNAME
MOTHER'S LAST
NAME
NAMES TELEPHONE CONTACT

EDUCATIONAL DISTRICT
SLLLD
EDUCATIONAL
UNIT
Final_________| J Private j Convention
MAXIMUM TEST TIME: 90 minutes
THE USE OF A PERIODIC TABLE IS ALLOWED, THE USE OF A CALCULATOR IS NOT ALLOWED

QUESTIONS. (10 POINTS C. OR.)

1. According to the reaction:

potassium hydroxide + sulfuric acid — • potassium sulfate + water
15 g of pure sulfuric acid was reacted with excess pine potassium hydroxide and 13.3 g of potassium sulfate
was obtained. What was the yield of the reaction?
a) 30% b) 80% c) 45% d) 50% e) 5%
2. In the reaction:
MnO2 + HBr —- MnBr + Br2 + H:O
80 grams of Br2 are produced. The mass of MnO2 that reacts is:
a) 43.5 g b) 87 g c)4.35 g d) 0.435 g e) 8.7 g
3. For the following reaction:
calcium carbonate + heat —- calcium oxide + carbon dioxide
If 200 grams of 90% pure sample are reacted with calcium carbonate and 1.35 moles of calcium oxide are
obtained , the reaction yield will be:
a) 70% b) 75 % c) 80% d) 85 % e) 90%
4. Viscosity is a characteristic physical property of:
a) solids only b) liquids only c) gases only
d) solids and liquids e) liquids and gases
5. They are incompressible bodies:
a) solids b) liquids c) gases
d) solids and liquids e) liquids and gases
6. In 56 liters of CO2, measured under normal pressure and temperature conditions, the amount in grams of this
gas is:
a) 100 b) 1 10 c) 120 d) 44 e) none
7. Under normal conditions of pressure and temperature, one liter of a gas weighs 0.759 grams. The molecular
weight of the gas is:
a) 17 g mol b) 34 g mol c) 128 g mol d) 29 g mol e) none
8. On Juancito Pinto's birthday , 224 balloons of 3 liters each were inflated, under normal conditions, with
helium from a tank that was initially at 27°C and 6 atm pressure . The volume of the tank is:
a) 120 liters b) 123 liters c) 125 liters d) 129 liters e) none
9. 12 grams of NaCl are dissolved in 108 grams of water. The weight percentage of the solution is:
a) 12 % b) 1 1.1 % c) 10 % d) 12.5 % e) none
10. A solution contains 212 grams of sodium carbonate in 0.5 liters of solution. Its molar concentration is:
a) 8M b)0.5M c) 1 M d) 2 M e)4M
 Nomenclature of Organic Chemistry - 225 -

RESPONSES TO SELF-ASSESSMENT PRACTICES

1C 2.- b 3.- c 4.- d 5.- b 6c 1C 2.b 3. a 4.b 5. c 6. a

7.- to 8.- d 9.- d 10.- d 11.- d 12.- d 7.b 8. c 9th 10.b
13.- c 14.- c 15.- b 16.- c 17.- d 18
19.- d 20.- b 21.- c 22.- d
Introduction to organic chemistry (I) Alkynes (II)
Cyclic hydrocarbons (I)
Introduction to organic chemistry (II) 1B 2. c 3. a 4. c 5.b 6c
7th 8. to 9.b 10. c
1C 2.- d 3.- b 4.- c 5.- b 6.- to
7.- b 8.- c 9.- d 10.- b 11.- b 12.- c
13.- c 14.- c 15.- b 16.- to 17.- c 18.- b
Cyclic hydrocarbons (II)
19.- c 20.- b 21.- d 22.- c 23.- to 24.- to
25.- to
1. to 2. c 3. b 4. c
7. b 8. b 9. to 10. c 5. a 6c
Alkanes (I)
Aromatic hydrocarbons (I)
1. c 2. to 3. b
4. a
7. c 8. b 9. to 5. c 6.b 5.b 6c
10. c 1. c 2. to 3. b 4. to
7. b 8. to 9. c 10. b
Alkyl radicals

1. to 2. b 3. c 4.b 5. a 6c Aromatic hydrocarbons (II)

7th 8. b 9. c 10. a
1. b 2. c 3. to 4. c 5.b 6. a
7. to 8. c 9. b 10. b
Alkanes (II)

1. to 2. c 3.b 4.b 5.b 6c Alcohols (I)

7. c 8. to 9.c 10.b
1B 2. c 3. a 4. c
5.b 6.b
7th 8. c 9th 10.b
Alkenes (I)

1. b 2. c 3. b 4. c 5.b 6. a Alcohols (II)

7. c 8. to 9. c 10.b
1C 2. b 3. a 4. a
5. c 6.b
7.b 8. c 9th 10.b
Practice 7: Alkenes (II)

1B 2. to 3. c 4. a 5.b 6. a Practice 16: Phenols (I)

7. c 8. b 9.c 10. c
1. b 2. to 3. c 4. c
5. a 6.b
7. b 8. b 9. to 10. c
Alkynes (I)

1. b 2. c 3. a 4. c 5.b 6.b Phenols (II)

7th 8. to 9th 10.b
1. to 2. c 3.b 4. c
7.b 8. b 9th 10. c 5. a 6c
- 226 - Nomenclature of Organic Chemistry

Ethers (I) Amides (I)

1. to 2.b 3. c 4.b 5. a 6.b 1B 2nd to 3. c 4. c 5. a 6.b
7.b 8. c 9th 10. a 7.b 8th 9.c 10.b

Ethers (II) Amides (II)

1B 2. c 3. a 4. c 5.b 6. a 1B 2. b 3. a 4. a 5. c 6. a
7.b 8. c 9.b 10. a 7.b 8. c 9.b 10. c

Aldehydes (I) Amines (I)

3.b 4. c 5. c 6c 3. c 4.b 5. a 6.b

7th 8. b 9th 10. c 7th 8. c 9.b 10. a

Aldehydes (II) Amines (II)

3. c 4. a 5.b 6. a 3. a 4. a 5.b 6. a
7. c 8. b 9. c 10. c 7. c 8. b 9. c 10. c

Ketones (I) Nitriles (I)

3.b 4. c 5. a 6c 3.b 4.b 5. a 6c

7th 8. b 9. c 10. a 7.b 8. to 9.c 10. a

Ketones (II) Nitriles (II)

3.b 4.b 5. c 6c 3. a 4. a 5.b 6c

7.b 8.b 9th 10. a 7th 8.b 9.c 10. c
BIBLIOGRAPHY CONSULTED

Carboxylic acids (I) Nitro compounds (I)

1. c 2. b 3. to 4.b 5.b 6c
1. to 2. c 3. c 4. b 5.b 6c
7. to 8. c 9. to 10.b
7th 8. c 9. to 10. b

Nitro compounds (II)

Carboxylic acids (II)

1. b 2. c 3. b 4. c 5. to 6. c 1. c 2. b 3. to 4. to 5. c 6. c
7.BURTON
to 8. Donald
b J. and
9. to Routh
10. cJoseph I. “Organic Chemistry7.and
to Biochemistry”
8. b 9.Editorial
b Interamericana,
10. c

Esters (I)

1B 2. to 3. c 4. to 5. c 6. b
7.b 8. b 9. c 10. to

Esters (II)

1C 2. b 3. to 4. to 5. b 6c
7. to 8. b 9. c 10. c
 Nomenclature of Organic Chemistry - 227 -

Mexico 1977.

MORRISON and Boyd, Organic Chemistry, fifth edition. Pearson education, Mexico 1998.

SOLÍS Correa Hugo E. “Chemical Nomenclature”, Ed. McGraw Hill, Mexico 1994.

CHANG Raymond “Chemistry”, Mc Graw Hill publishing house, Sixth edition, Mexico 1999.

ZAVALA Chávez Jesús Gabriel, Chemistry Notes II, Puruándiro 2000.

CORTEZ Aranda Victor Hugo. “Chemistry4”,Ed. Don Bosco, La Paz 2009.

earthenware B. Juan and ALMENDRAS C. Juan. “Organic chemistry”. Ed. Latinas editors, fourth edition, Oruro
2007.

WEEBGRAPHY

http://www.alonsoformula.com/organica
http://www.heurema.com/DFQ17.htm
http://www.unicoos.com/
http://www.youtube.com/watch?v=czAOF8Yhdk8&feature=relmfu
http://www.ciens.ucv.ve/quimicaorg/clases%20org%20i/iupac-form-organica.pdf
http://www.salonhogar.net/quimica/nomenclatura_quimica
http://www.sinorg.uji.es/Docencia/QO.pdf
http://www.quimicaorganica.org/index.php
http://html.rincondelvago.com/formulacion-y-nomenclatura-organica.html
http://organica1.org/nomencla/nomencla.htm
http://www.ciens.ucv.ve/quimicaorg/clases%20org%20i/iupac-form-organica.pdf
http://www.jpimentel.com/ciencias_experimentales/pagwebciencias/pagweb/materias/quimica_2_bach/quimica_
links_u10.htm
http://organica1.org/rafael/index.html
http://www.buenastareas.com/ensayos/Qmc-Organica/3045544.html
http://cabierta.uchile.cl/libros/h_vmarttens2/
http://www.quimicaorganica.net/nomenclatura-alcanos.html
www.uhu.es/quimiorg/nomenclatura.html
http://www.uhu.es/quimiorg/nomenclatura.html
http://www.chem.qmw.ac.uk/iupac/
http://www.acdlabs.com/iupac/nomenclature
http://www.sci.ouc.bc.ca/chem/nomenclature/nom1.htm
http://www.equi.ucr.ac.cr/escuela/cursos