What is the difference between tautomerism and metamerism?

Jul 11, 2016

Tautomerism and metamerism are different types of structural isomerism.

Explanation:

Structural isomerism is a form of isomerism in which molecules have the same molecular formula but their atoms are connected in different orders.

Structural isomerism is divided into:

• Chain isomerism
• Positional isomerism
• Functional group isomerism
• Tautomerism
• Metamerism

Tautomerism

Tautomerism is a dynamic equilibrium between two compounds with same molecular formula.

The most common form of tautomerism is keto-enol tautomerism.

A carbonyl compound containing at least one α-hydrogen atom is converted to an enol by the transfer of an α-hydrogen onto the oxygen atom. For example,

(from chemwiki.ucdavis.edu)

Metamerism

Metamerism is a type of structural isomerism in which different alkyl groups are attached to the same functional group.

For example, diethyl ether and methyl propyl ethers are metamers.

$\underbrace{\text{CH"_3"CH"_2"-O-CH"_2"CH"_3)_color(red)("diethyl ether}}$ and $\underbrace{\text{CH"_3"-O-CH"_2"CH"_2"CH"_3)_color(red)("methyl propyl ether}}$

They both contain the ether functional group, but they have different alkyl groups attached to the oxygen atom.