Organic Chemistry
1 2 3 4 bonds
HONC
What is organic chemistry?
• study of carbon, the compounds it makes,
and the reactions it undergoes
• over 16 million carbon-containing
compounds are known
• because the C-C single bond (348 kJ mol-1)
and the C-H bond (412 kJ mol-1) are strong,
carbon compounds are stable
• carbon can form chains and rings
Homologous series/compounds
(10.1.1)
• related compounds that have the same
functional group (groups of atoms found
within molecules that are involved in the chemical
reactions characteristic of those molecules)
• differ from each other by a CH2 unit
• can be represented by a general
formula
– examples:
• CnH2n+2 (alkanes) or CnH2n (alkenes) or…
• have similar chemical properties
• have physical properties that vary in
a regular manner as the number of
carbon atoms increases
– Example: the alkanes
Trends in boiling points of members of
a homologous series (10.1.2)
• melting point and
Alkane Formul Boiling
boiling point a Pt./oC
increase with more
carbon atoms
methan CH4 -162.0
• Why? e
– intermolecular
forces increase ethane C2H6 -88.6
– adding a CH2 adds
more electrons propan C3H8 -42.2
• this increases the
e
Van der Waal’s butane C4H10 -0.5
forces
Empirical, molecular & structural formulas
(10.1.3)
Empirica Molecula
• empirical l Formula r
formula Formula
– simplest ratio CH4 CH4
of atoms in a CH3 C2H6
molecule
• molecular CH2O C6H12O6
formula CH2 C4H8
– actual
numbers of CH2 C8H16
atoms in a
molecule
structural formula
• unambiguously shows how the atoms are
bonded together
• can use condensed structural formulas
– bonds are omitted, repeated groups
put together, side chains put in
brackets
• CH3CH2CH2CH2CH2CH3
– or even CH3(CH2)4CH3
• CH3CH(CH3)CH3
condensed
skeletal formula
– every “corner” represents a carbon
– hydrogens are implied
Isomers (10.1.4)
• (structural) isomers: compounds with
the same molecular formula but different
structure (arrangement of atoms)
• different isomers are completely different
compounds
• have different physical properties such as
melting point and boiling point
Structural
Formulas
for C4H10O
Isomers
Alkanes
Structural formulas for the isomers of
non-cyclic alkanes up to C6 (10.1.5)
• hydrocarbon chains where all the bonds between carbons are
SINGLE bonds
• CnH2n+2
• draw out and write the structural formulas for all
isomers that can be formed by:
– CH4
– C2H6
Richard Thornley 10.1.5
– C3H8 2:54
– C4H10
– C5H12
– C6H14
Naming the isomers (IUPAC) of non-
cyclic alkanes up to C6 (10.1.6)
1. Richard Thornley 3:35
2. Determine the longest carbon chain
– Use the prefix to denote the number carbons
1 Meth-
2 Eth-
Monkeys
3 Prop-
4 But- Eat
5 Pent- Peeled
6 Hex-
Bananas
3. use the suffix “-ane” to indicate that the
substance is an alkane
4. number the carbons in the chain
consecutively, starting at the end closest
to a substituent (groups attached to the
main chain/most busy end)
5. name and number the location of each
substituent
– the name of the substituent will be written before
the main chain and will end with “–yl” (or just
memorize the below)
• CH3 is methyl
• C2H5 is ethyl
• C3H7 is propyl
And with 2 or more side chains:
6. use prefixes di-, tri-, tetra-, to indicate
when there are multiple side chains of the
same type
7. use commas to separate numbers and
hyphens to separate numbers or letters.
• How about C5H12? The isomers are:
Pentane 2-methyl-butane 2,2-dimethyl propane
Nomenclature Practice
Name this compound
CH3
H3C1 CH3 9 carbons = nonane
2 3 4 5
6
Cl
7
8
H3C9
Step #1: For a branched hydrocarbon, the longest
continuous chain of carbon atoms gives the root
name for the hydrocarbon
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
Step #2: When alkane groups appear as substituents, they are named
by dropping the -ane and adding -yl.
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
1 9 NOT 9 1
Step #3: The positions of substituent groups are
specified by numbering the longest chain of
carbon atoms sequentially, starting at the end
closest to the branching.
Nomenclature Practice
Name this compound
CH3
9 carbons = nonane
H3C1 CH3
2 3 4 5
6 CH3 = methyl
Cl
7
8 chlorine = chloro
H3C9
2-chloro-3,6-dimethylnonane
Step #4: The location and name of each substituent
are followed by the root alkane name. The
substituents are listed in alphabetical order
(irrespective of any prefix), and the prefixes di-, tri-,
etc. are used to indicate multiple identical
substituents.
Alkenes
Structural formulas for the isomers of the
straight chain alkenes up to C6 (10.1.7)
• alkenes have a double bond between two or
more of the carbons
• CnH2n
• draw out and write the structural formulas for all
isomers that can be formed by each
– C2H4
– C3H6 Richard Thornley 10.1.7 (1:37)
– C4H8
– C5H10
– C6H12
Naming the isomers (IUPAC) of straight
chain alkenes up to C6 (10.1.8)
1. suffix changes to “-ene”
2. when there are 4 or more carbon
atoms in a chain, the location of the
double bond is indicated by a
number
3. begin counting the carbons closest to
the end with the C=C bond
– numbering the location of the double
bond(s) takes precedence over the
location of any substituents
1-butene 2-butene
but-1-ene but-2-ene
Naming Practice!!!
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
choose the correct ending
ene
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
determine the longest carbon chain with
the double bond
ene
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
assign numbers to each carbon
ene
CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
assign numbers to each carbon
ene
CH2 CH2 CH3
1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
attach prefix (according to # of carbons)
1-hexene
ene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
determine name for side chains
1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
attach name of branches alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
CH2 CH2 CH3
ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
group similar branches
2-ethyl-4,4-dimethyl-1-hexene
or 2-ethyl-4,4-dimethyl hex-1-ene
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3
CH3 CH CH CH3
2,4-dimethyl-2-pentene
2-butene 2,4-dimethyl pent-2-tene
CH3 CH3
CH2 CH C CH2 CH3 CH3 C CH CH2
CH3 CH2 CH3
a) 3,3-dimethyl-1-pentene b) same
CH 3
CH 3 C C CH CH CH3
CH3
c) 4,5 dimethyl-2-hexene
