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An aromatic compound 'A' on heating with aqueous ammonia forms compound 'B'. Compound 'B' on heatingAmines Chemistry Question

Question

An aromatic compound 'A' on heating with aqueous ammonia forms compound 'B'. Compound 'B' on heating with $Br_2$ and $KOH$ produces a compound 'C' with the molecular formula $C_6H_7N$. Identify the starting compound 'A'.

Answer: A

💡 Solution & Explanation

Compound 'C' is aniline ($C_6H_5NH_2$). It is produced from 'B' via the Hofmann bromamide degradation using $Br_2/KOH$. This dictates that 'B' must be benzamide ($C_6H_5CONH_2$). Benzamide is synthesized by reacting benzoic acid ('A', $C_6H_5COOH$) with ammonia to form ammonium benzoate, followed by thermal dehydration.

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