Compounds having the same molecular formula, but differing in physical and chemical properties are known as

isomers. This phenomenon is known as isomerism. The isomers can be identified and distinguished from one
another because of difference in their physical and chemical properties.

Types of Isomerism
Isomerism may be classified into two types viz.,

 Structural isomerism

 Stereo isomerism

These are further classified into different classes as follows:

Structural Isomerism
Structural isomerism arises due to the difference in the arrangement of atom in the molecule i.e., the isomers
have different structure. There are five different ways in which the structural isomerism arises. These are:

Chain isomerism
This type of isomerism arises from the difference in the nature, structure of the carbon chain. For example, for
butane (C4H10), the following arrangements are possible.

Pentane (C5H12) exhibits the following three structures.

 

Butanol (butyl alcohol) has the following two structures of the carbon chain.

For butanal, (C3H7CHO), the following chain isomers are possible.

Position isomerism
This isomerism arises due to the difference in the position of the same functional group or the same substituent
while the arrangement of carbon atoms remains same. For example,

Chloropropane (C3H7Cl) can have two positional isomers given below.

 
 

Butene (C4H8) can have two positional isomers.

Propanol (C3H7OH) has the following positional isomers.

Functional isomerism
The compounds having the same molecular formula but different functional groups are said to exhibit functional
isomerism. Such compounds are termed functional isomers. For example, there are two compounds having the
molecular formula C2H6O viz.,

Ether

 
 

Alcohol

The molecular formula C3H6O represents two functional isomers.

Aldehyde

Ketone

Metamerism
This type of isomerism arises from the unequal distribution of carbon atoms on either side of the functional
group in the molecule of compounds belonging to the same homologous series. For example, diethyl ether and
methylpropyl ether are metamers.

A ketonic compound having the molecular formula C5H10O, has the following two metamers.

Tautomerism
This is a special case of functional isomerism. Certain substances can

exhibit properties of two functional groups as for instance, acetoacetic ester behaves like a ketone as well as an
alcohol. This arises due to the migration of a labile hydrogen atom from one place to another.In acetoacetic ester,
the inter-conversion between keto and enolic group takes place as follows.

 
 

In amides, it happens as follows:

Both these forms of the same molecule exist in equilibrium in a sample of compound. The migration of a labile
hydrogen between two polyvalent atoms in the same molecule causes this type of dynamic isomerism. This is
termed as tautomerism or keto-enol tautomerisn. Such isomers are termed as tautomers.

Problems
1. An alkane has a molecular mass of 72. Draw its possible chain isomers.

Solution
First of all, we will derive the molecular formula.

Molecular formula of alkane is CnH2n+2

As molecular mass = 72,

12n + 2n + 2 = 72

n=5

The alkane is C5H12. The possible chain isomers are

and

 
2. What are the possible structures for a carboxylic acid with the molecular formula C4H8O2?

Solution
The possible structures for the carboxylic acid are:

3. Write structural formulas for all the isomeric amines with molecular formula C4H11N.

Solution