Write a short note on Hoffmann bromamide degradation.
Explain Hoffmann bromamide degradation reaction
Solution 1
(a)Hoffmann Bromanide degradation
(1) The conversion of amides into amine in presence of bromine and alkali is known on Hoffmann degradation of amides.
(2) An important characteristic of this reaction is that on amine with one carbon less than those in the amide is formed.
(3) This reaction is an example of molecular rearrangement and involves migration of an alkyl or aryl group from the carbonyl carbon to this adjacent nitrogen atom.
Example:
Solution 2
Hoffmann bromamide reaction:
a) Primary amine can be prepared by reaction of amide with bromine and aqueous or
alcoholic sodium hydroxide.
eg. Ethanamine is prepared by reaction of propanamide with bromine and aqueous or
alcoholic sodium hydroxide.
b) This reaction is known as Hoffmann bromamide degradation. It involves molecular
rearrangement. An alkyl or aryl group migrates from the carbonyl carbon to the
adjacent nitrogen atom.
c) This reaction is useful for decreasing the length of carbon chain by one carbon atom.
