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Curtius and Hofmann Rearrangements

An aromatic c...

Question

An aromatic compound $A$ on treatment with aqueous ammonia and heating forms compound $B$ which on heating with $B r_{2}$ and $K O H$ forms a compound $C$ of molecular formula $C_{6} H_{7} N$ . Write the structures and IUPAC names of compounds $A, B$ and $C$ .

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Solution

The aromatic compound $A$ is benzoic acid $C_{6} H_{5} C O O H$ .
On treatment with aqueous ammonia and heating forms compound B, which is benzamide $C_{6} H_{5} C O N H_{2}$ .
Benzamide on heating with bromine and $K O H$ forms a compound $C$ of molecular formula $C_{6} H_{7} N$ , which is aniline $C_{6} H_{5} N H_{2}$ . The reaction is called Hoffmann bromamide degradation.

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