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Isomerism

N Goalby
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1. Chain isomerism
These isomers arise because of the carbon chains can be
branched. For example, there are two isomers of butane,
C4H10. In one of them, the carbon atoms lie in a "straight
chain" whereas in the other the chain is branched
H H H
H H H H
H C C C H
H C C C C H
H H
H C H
H H H H
H

butane methyl propane

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False Isomers
Do not draw "false" isomers which are just twisted versions
of the original molecule.

H H H H H H H

H C C C H
H C C C C H
H H
H C H
H H H H
H

H C HH
These are all exactly the
same compound.
H C C H

H
H C H

Pentane, C5H12, has three chain isomers.

H H H H
H H H H H
H C C C C H

H C C C C C H H H H
H C H
H H H H H H

pentane 2-methyl butane

H C H
H H

H C C C H

H H
H C H

2,2-dimethyl propane

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Number of Possible Isomers for Selected Alkanes

Molecular Formula Number of possible

isomers
C4H10 2
C5H12 3
C6H14 5
C7H16 9
C8H18 18
C9H20 35
C10H22 75
C15H32 4,347
C20H42 336,319
C30H62 4,111,846,763

2. Position isomerism
In position isomerism, the basic carbon skeleton remains
unchanged, but functional groups are moved around on that
skeleton.

For example, there are two structural isomers with the molecular
formula C3H7OH. In one of them the hydroxyl group is on the end of
the chain, whereas in the other it's attached in the middle.
H H H
H H H

H C C C H
H C C C O H

H O H
H H H
H
Propan-1-ol Propan-2-ol
It is possible to have a mixture of chain isomerism and position
isomerism – it is not restricted to one or the other

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3. Functional group isomerism

In this variety of structural isomerism, the isomers have the
same molecular formula but contain different functional
groups - eg an aldehyde or a ketone.
H H H
H

H C C O H H C O C H

H H H H

ethanol: an alcohol Methoxy methane: an ether

H H O H O H

H C C C H C C C H

H H H
H H

Propanal: an aldehyde Propanone: a ketone

Structural isomerism in alkenes

This can be a result of:

Positional Isomerism
CH2 CH CH2 CH
H3 C CH2 CH2 H 3C CH3
CH

Pent-1-ene Pent-2-ene

• Chain Isomerism (Branching)

CH CH3
H 2C CH
3-methylbut-1-ene
CH3

KEY