Write a note on Hofmann bromamide degradation.

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Solution

Hofmann bromamide degradation:
Treatment of an $a m i d e$ with $b r o m i n e$ and aqueous / alcoholic $s o d i u m h y d r o x i d e$ gives a $p r i m a r y a m i n e$
$R - C O N H_{2} + B r_{2} + 4 N a O H \to R - N H_{2} + N a_{2} C O_{3} + 2 N a B r + 2 H_{2} O$
The product $a m i n e$ contains one carbon atom less than starting $a m i d e$ . This reaction involves migration of an alkyl or aryl group from the carbonyl carbon to the adjacent nitrogen atom.
For example, $p r o p a n a m i d e$ on Hofmann bromamide degradation gives $e t h a n a m i n e$
$C H_{3} - C H_{2} - C O N H_{2} + B r_{2} + 4 N a O H \to C H_{3} - C H_{2} - N H_{2} + N a_{2} C O_{3} + 2 N a B r + 2 H_{2} O$

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