ISOMERISM

The existence of two or more substances with the same molecular formula, but different
structures, is called isomerism. The structures are isomers. Since isomers are different
substances, they have different properties such as melting point, boiling point, etc.
There are several kinds of isomers:
a) structural (or skeleton isomers),
b) positional isomers
c) functional isomers
d) geometric isomers
1) STRUCTURAL (SKELETON) ISOMERS. They have different carbon chains, for example:

Molecular formula: C5H12

Condensed structural formulae:
CH3
|
CH3 C CH3
|
CH3
(neo pentane)

CH3 CH2 CH2 CH2 CH3

(pentane)

2) POSITIONAL ISOMERS. They are two compounds that differ only in the position of
something such as a double bond or an atom other than hydrogen and carbon (a functional
group), for example:

a) Molecular formula: C4H10O

Condensed structural formulas:
OH
|
CH3 CH2 CH2 CH2

OH
|
CH3 CH2 CH CH3

(1 butanol )

(2 butanol )

b) Molecular formula: C4H8

Condensed structural formulas:
CH2 = CH CH2 CH3
( 1 butene )

CH3 CH = CH CH3
( 2 butene )

3) FUNCTIONAL
groups.

ISOMERS. They have the same atoms arranged in different functional

There are several pairs of functional groups that can be functional isomers:

a)
b)
c)
d)
e)
f)

Aldehyde ketone
Alcohol ether
Carboxylic acid ester
Alkene cycloalkane
Alkyne cycloalkene
Alkyne alkene with 2 double bonds

Aldehyde ketone
CH3 CH2 CH = O
O
||
CH3 C CH3

alcohol ether

carboxylic acid ester

CH3 CH2 CH2 OH

CH3 CH2 COOH

CH3 CH2 O CH3

CH3 COO CH3

alkene cycloalkane

Alkyne cycloalkene

CH3 CH = CH CH3

CH3 C C CH3

CH2 CH2
|
|
CH2 CH2

CH = CH
|
|
CH2 CH2

4) GEOMETRIC ISOMERS. They are composed of the same atoms bonded in the
same order, but with different arrangement of atoms around a double bond. They are
called cis and trans forms
Example:
Molecular formula: C4H8
Condensed structural formula: CH3 CH = CH CH3
Space arrangement:
CH3

CH3
/
CH = CH

CH3
/
CH = CH
/
CH3

Cis 2-butene

Trans 2- butene

( CH3 on the same side of the double bond )

bond )

( CH3 in opposite sides of the double

Tips to avoid making mistakes

a) Carbon atoms chains can turn in a 180 angle, so the following pairs of formulae
ARE NOT ISOMERS, they are the same compound:
CH3 CH2 CH2 OH

HO CH2 CH2 CH3

CH3 CH CH2 CH3

|
Cl

CH3 CH2 CH CH3

|
Cl

b) The carbon atoms in a chain can bend the single bonds that join them, so the
following pairs of formulae ARE NOT ISOMERS, they are the same compound:

CH3 CH2 CH2 CH2

|
CH3

CH3
|
CH3 CH2 CH2 CH CH3

CH3 CH2 CH2 CH2 CH3

CH3
|
CH3 CH2 CH2 CH
|
CH3