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Question

An aromatic compound A on treatment with aqueous ammonia and heating forms compound B which on heating with Br2 and KOH forms a compound C of molecular formula C6H7N. Write the structures and IUPAC names of compounds A,B and C.

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Solution

The aromatic compound A is benzoic acid C6H5COOH.
On treatment with aqueous ammonia and heating forms compound B, which is benzamide C6H5CONH2.
Benzamide on heating with bromine and KOH forms a compound C of molecular formula C6H7N, which is aniline C6H5NH2. The reaction is called Hoffmann bromamide degradation.

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