Question
Write short notes on the following:
Hofmann’s bromamide reaction.
Hofmann’s bromamide reaction.
✓
Answer
Hoffmann bromamide degradation reaction: Hoffman develops a method for preparation of primary amines by treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide.
In this reaction migration of an alkyl or aryl group takes place from carbonyl carbon of the amide to the nitrogen atom. The amine so formed contains one carbon less than that present in the amide.
$ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{O}\\\ \ \ \ \ \ \ \ \ \ \ \ \ ||\\\text{CH}_3-\text{C}-\text{NH}_2+\text{Br}_2+4\text{KOH}\rightarrow{\\\\\\\\\\\\}\text{CH}_3\text{NH}_2\\\text{Ethanamide} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Methanamine}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ +\text{K}_2\text{CO}_3+2\text{KBr}+2\text{H}_2\text{O}$
In this reaction migration of an alkyl or aryl group takes place from carbonyl carbon of the amide to the nitrogen atom. The amine so formed contains one carbon less than that present in the amide.
$ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{O}\\\ \ \ \ \ \ \ \ \ \ \ \ \ ||\\\text{CH}_3-\text{C}-\text{NH}_2+\text{Br}_2+4\text{KOH}\rightarrow{\\\\\\\\\\\\}\text{CH}_3\text{NH}_2\\\text{Ethanamide} \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \text{Methanamine}\\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ +\text{K}_2\text{CO}_3+2\text{KBr}+2\text{H}_2\text{O}$
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