In which of the following reaction a primary amine with loss of carbon is produced?

R - C O N H_{2} + N a O H B r_{2} \to

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R - C O N H_{2} L i A l H_{4} \to

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R - C O N H_{2} N a B H_{4} \to

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All of the above

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Solution

The correct option is A $R - C O N H_{2} + N a O H B r_{2} \to$
a) Amine is formed but with one carbon atom lesser than present in the amide. It is called Hoffmann bromamide degradation.
$R - C O N H_{2} + N a O H B r_{2} \to R - N H_{2}$
b)

c) $N a B H_{4}$ reduces aldehydes, ketones and acid halides but can not reduce amides to amines.

Hence, the correct answer is option (a).

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