AIEEE Chemistry UNIT 20A PRINCIPLES OF ORGANIC CHEMISTRY

Isomerism






The existence of two or more compounds with same molecular formula but different properties (physical, chemical or both) is known as isomerism; and the compounds themselves are called isomers.

Isomerism types:

i) Chain, nuclear or skeleton isomerism

This type of isomerism is due to the difference in the nature of the carbon chain (i.e. straight or branched) which forms the nucleus of the molecule,

ii) Position isomerism

It is due to the difference in the position of the substituent atom or group or an unsaturated linkage in the same carbon chain.

iii) Functional isomerism



This type of isomerism is due to difference in the nature of functional group present in the isomers,


iv) Metamerism

It is due to the difference in nature of alkyl groups attached to the same functional group. This type of isomerism is shown by compounds of the same homologous series.

v) Tautomerism

Tautomerism may be defined as the phenomenon in which a single compound exists in two readily interconvertible structures that differ markedly in the relative position of at least one atomic nucleus, generally hydrogen. The two different structures are known as tautomers of each other.

Stereo isomerism

When isomers have the same structural formula but differ in relative arrangement of atoms or groups in space within the molecule, these are known as stereoisomers and the phenomenon as stereoisomerism. The spatial arrangement of atoms or groups is also referred to as configuration of the molecule and thus we can say that the stereoisomers have the same structural formula but different configuration. Stereoisomerism is of two types.

(i) Geometrical isomerism

The isomers which possess the same structural formula but differ in the spatial arrangement of the groups around the double bond are known as geometrical isomers and the phenomenon is known as geometrical isomerism.

ii) Optical isomerism


This type of isomerism arises from different arrangements of atoms or groups in three dimensional space resulting in two isomers which are mirror image of each other. Optical isomers contain an asymmetric (chiral) carbon atom ( a carbon atom attached to four different atoms or groups) in their molecules.