Chapter 13.
0 :
HYDROCARBONS
At the end of the lesson students should be able to:
a) Define hydrocarbon compounds
b) Classify hydrocarbons into :
i) aliphatic and aromatic ii) saturated and unsaturated
c) Decscribe alkanes as saturated by hydrocarbon with the general
formula :
i) CnH2n+2 , n > 1 for open chain alkanes
ii) CnH2n , n >3 for cycloalkanes
d) Draw the structures and name the compounds according to the
IUPAC nomenclature for :
i) straight chain and branched alkanes (C1-C5 )
ii) cyclic alkanes (C3-C6 ) iii) alkyl groups
13.1 : ALKANES
Hydrocarbon
are compounds which
contain only carbon and
hydrogen atoms.
HIDROCARBONS
AROMATIC
ALIPHATIC
(contain one or more benzene ring)
ALKANES ALKENES
(saturated) (unsaturated) ALKYNES
contain only contain (unsaturated)
single bond C=C contain
CC
CYCLO-ALKANES (saturated) CYCLO-ALKENES
Alkanes which C atoms are (unsaturated)
join in rings
Saturated hydrocarbons
- compound with C-C
- Example : alkanes and cycloalkanes
Contain the maximum number of
hydrogen atoms that the carbon
compound can possess.
Unsaturated hydrocarbons
-compounds with multiple bonds
-Example : alkenes, cycloalkenes, alkynes
and aromatic hydrocarbons
They posses fewer than the maximum
number of hydrogen atoms.
ALKANES
Alkanes are known as saturated hydrocarbon
which contain only single covalent bonds.
General formula for straight chain of alkanes is
CnH2n+2 where n 1
General formula for cycloalkanes
is CnH2n where n 3
Each carbon atom in alkanes is
sp3 hybridised
tetrahedral with four sigma bond (formed by
the four sp3 hybrid orbitals.)
all bond angles are close to 109.5o
Alkanes IUPAC names have the ane suffix.
The First Ten Unbranched Alkanes
Molecular Structural formula No .of C Name
formula atoms
CH4 CH4 1 Methane
C2H6 CH3CH3 2 Ethane
C3H8 CH3CH2CH3 3 Propane
C4H10 CH3(CH2)2CH3 4 Butane
C5H12 CH3(CH2)3CH3 5 Pentane
C6H14 CH3(CH2)4CH3 6 Hexane
C7H16 CH3(CH2)5CH3 7 Heptane
C8H18 CH3(CH2)6CH3 8 Octane
C9H20 CH3(CH2)7CH3 9 Nonane
Starting from C4H10 onwards, the alkanes show
the phenomenon of chain isomerism.
They can exist as linear or branched alkanes.
Example
C4H10
2-
isobutane
CH3(CH2)2CH3 CH3CH(CH3)2
C5H12
IUPAC NOMENCLATURE
IUPAC International Union of Pure and
Applied Chemistry
Branched - chain alkanes are named
according to the following rules:
Choose the longest continuous chain of
carbon atoms; this chain determines the parent
name for alkanes.
Examples:
CH3CH2CH2CH2CHCH3
|
CH3
Parent name: hexane
CH3CH2CH2CH2CHCH3
CH2
CH3
Parent name : heptane
Number the longest chain beginning with the
end of the chain nearer the substituent.
Example:
6 5 4 3 2 1
CH3CH2CH2CH2CHCH3
CH3 substituent
7 6 5 4 3
CH3CH2CH2CH2CH CH substituent
3
|
2CH2
|
1 CH3
Use rule number 2 to locate the position of the
substituent.
The position and the name of the substituent
must be written in front of the parent chain.
Examples:
6 5 4 3 2 1
CH3CH2CH2CH2CHCH3
Substituent
CH3 -methyl at C-2
2-methylhexane
Substituent
7 6 5 4 3 -methyl at C-3
CH3CH2CH2CH2CH CH3
|
2 CH
2
|
1
CH3
3-methylheptane
Some Common Substituent Groups
Alkane name substituent
methane methyl CH3
ethane ethyl CH2CH3
propane propyl CH2CH2CH3
CHCH3
isopropyl
CH3
butane butyl CH2CH2CH2CH3
isobutyl CH2CHCH3
CH3
sec-butyl
CHCH2CH3
CH3
tert-butyl CH3
CCH3
CH3
neopentyl CH3
CH2CCH3
CH3
cyclopropyl
cyclobutyl
phenyl
C6H5 or
benzyl
CH2
name substituent
Bromo -Br
Chloro -Cl
Flouro -F
Iodo -I
Hydroxyl -OH
Amino -NH2
Cyano -CN
Nitro -NO2
If two or more substituents are present, give
each substituent a number corresponding to its
location on the longest chain.
the substituent should be listed alphabetically.
In alphabetizing, the prefixes di, tri, tetra, sec-,
tert- are ignored except iso and neo.
Example:
1 2 3 4 5 6
CH3CHCH2CHCH2CH3
| |
CH3 CH2
|
CH3
4-ethyl-2-methylhexane
If two substituents are present on the same
carbon atom, use that number twice
Example:
CH3
|3 4 5 6
CH3CH2CCH2CH2CH3
|
2
CH2
|
1
CH3
3-ethyl-3-methylhexane
If two or more identical substituents are
present, use prefixes di-(2 identical
substituents),tri-(3 identical substituents),
tetra-(4 identical substituents).
Commas are used to separate numbers from
each other.
Example:
CH3CHCH CH3
| | 2,3-dimethylbutane
CH3 CH3
If there are two chains of equal length as the
parent chain, choose the chain with the
greater number of substituents.
7 6 5 4 3 2 1
4 3 2 1
CH3CH2-CH CH CH CHCH3
| | | |
CH3 5 CH2 CH3 CH3
|
6
CH2
7
|
CH3
2,3,5-trimethyl-4-propylheptane
(four substituents)
4-sec-butyl-2,3-dimethylheptane
(three substituents)
If branching occurs at an equal distance from
either end of the longest chain, choose the
name that gives the lower number at the first
point of difference.
6 5 4 3 2 1
CH3CHCH2CH CHCH3
1 2 3 4 5 6
| | |
CH3 CH3 CH3
2,3,5-trimethylhexane
(NOT 2,4,5-trimethylhexane)
CYCLOALKANES
Cycloalkanes alkanes which carbon atoms are
joined in rings.
Cycloalkanes are known as saturated
hydrocarbon, because it has the maximum
number of bonded hydrogen
(only has single bonds).
General formula:
CnH2n where n = 3, 4, 5,
NOMENCLATURE OF
CYCLOALKANES
Cycloalkanes with only one ring are named with
the prefix cyclo- to the names of the alkanes
(contain the same number of carbon atoms)
Examples: Monocyclic compounds
C3H6 cyclopropane
C4H8 cyclobutane
C5H10 cyclopentane
If only one substituent is present, it is not
necessary to designate its position.
Examples:
Chlorocyclopropane
Cl
CH3 Methylcyclohexane
If two substituents are present, number
carbon in the ring beginning with the
substituent according to the alphabetical
order
and
number in the direction that gives the next
substituent the lowest number possible.
Examples:
CH3
3
2
4 CH2CH3
1
5 6
1-ethyl-2-methylcyclohexane
NOT
1-ethyl-6-methylcyclohexane
2
Cl 3 1
Cl
4 5
1,3-dichlorocyclopentane
(NOT 1,5-
dichlorocyclopentane)
When three or more substituents are present,
begin at the carbon with substituent that leads
to the lowest set of locants.
Locants
Example:
CH2CH3 chloro 1 4
2 3
1
3 2
4 ethyl 3 2
Cl 4 1 CH3
5 6 methyl 4 1
6 5
1-chloro-3-ethyl-4-
methylcyclohexane
4- chloro-2-ethyl-1-
methylcyclohexane
H3C CH2CH3
CH3
1-ethyl-1,3-dimethylcyclopentane
(NOT 3-ethyl-1,3-dimethylcyclopentane)
When a single ring system is attached to a
single chain with a greater number of carbon
atoms
or
when more than one ring system is attached
to a single chain, then it is appropriate to name
the compounds as cycloalkylalkane.
Number of C at ring Number of C at
linear chain
Notes!
In the case of cycloalkane with an attached
alkyl substituent, the ring is the parent
hydrocarbon
Unless
The substituent has more carbons than the
ring. In that case, the substituent is the
parent hydrocarbons and the ring is named
as a substituent
-Organic Chemistry, Paula Yurkanis Briuce, page 71-
1 3
1,3-dicyclohexylpropane
Examples:
CH2CH2CH2CH2CH3
1-cyclobutylpentane
