If acetamide is treated with the following reagents separately, which one of these would yield methylamine?

$H o t c o n c H_{2} S O_{4}$

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Sodalime

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$N a O H - B r_{2}$

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$P C l_{5}$

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Solution

The correct option is C
$N a O H - B r_{2}$

Hoffmann’s bromamide reaction uses $N a O H - B r_{2}$ to convert amides to amines. One of the mechanisms through which this happens is as follows:

For this question, we just need to have a methyl group in the place of $R$ .

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A c e t a m i d e

m e t h y l a m i n e ?

Acetamide is treated separately with the following reagents. Which would give methyl amine

[IIT 1983; CPMT 1988, 94; MP PET 1993;

MP PMT 1996; AIIMS 1998]

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