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

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'.

Prashant Kotian · Accepted Answer

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

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