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Question

Propylamine can be obtained from Hoffmann bromamide reaction by using which of the following amide?

A
Propanamide
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B
Methanamide
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C
Ethanamide
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D
Butanamide
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Solution

The correct option is D Butanamide
When an amide is treated with bromine in an aqueous or ethanolic solution of sodium hydroxide, degradation of amide takes place leading to the formation of primary amine. This reaction involving degradation of amide and is popularly known as Hoffmann bromamide degradation reaction. The primary amine thus formed contains one carbon less than the number of carbon atoms in that amide.

CH3CH2CH2CONH2Br2+4NaOH−−−−−−−CH3CH2CH2NH2

It is Hoffmann bromamide degradation reaction in which an amide (butanamide) is converted to an amine (propylamine) containing one carbon atom lesser than in the amide. Hence, the correct answer is option (c).

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