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Question

Which of the following amines will not give Hoffman-Bromamide reaction?

A
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B
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C
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D
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Solution

The correct option is D
Hoffman-Bromamide reaction is used for preparing primary amine from primary amides. In this degradation reaction, migration of alkyl/aryl group takes place from carbonyl carbon of amide to the nitrogen atom.
(a) It is a primary amide and hence it will give Hoffman-Bromamide reaction.
(b) It is a primary amide and hence it will give Hoffman-Bromamide reaction.
(c) It is a primary amide where nitrogen is attached with bromine atom which is an intermediate of Hoffman-Bromamide reaction.
(d) It is a secondary amide and hence it will not give Hoffman-Bromamide reaction.

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