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Question

Propanamide on treatment with bromine in an aqueous solution of sodium hydroxide gives:

A
Propanamine
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B
Butanamine
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C
Ethanamine
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D
Methanamine
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Solution

The correct option is C Ethanamine
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.

The general reaction is as follows:
RCONH2AmideBr2+4NaOH−−−−−−−RNH21Amine+Na2CO3+2NaBr+2H2O

The reaction is as follows:

Hence c is the correct option.

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