Hofmann Degradation

Amide is treated with bromine or chlorine in alkali solution converts to primary amine

This reaction was discovered by hofmann in 1882 and results in the formation of primary amine by elimination of carbonyl group from an amide this reaction is called hofmann degradation 

Mechanism :-

Step1 : Base catalysed bromination of amide produces N-bromo amide.

Step2 : N-bromo amide react with alkali (sodium hydroxide) to yield acyl nitrene ion.

Step3 : The R-group of nitrene then migrates or rearrangement to form a relatively stable intermediate called isocyanate.

Step4 : The isocyanate finally react with water to give unstable carbonic acid which eliminates a molecule of carbon dioxide to yield primary amine.

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