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An aromatic compound 'A' on treatment wi...

An aromatic compound 'A' on treatment with aqueous ammonia and heating forms compounds 'B' which on heating with `Br_2` and KOH forms a compound 'C' of molecular formula `C_6 H_7 N`.
The compound 'B' is

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(i) Since the compound C of molecular formula `C_(6)H_(7)N` is formed from B on treatment with `Br_(2)` and KOH (Hoffmann bro- mamide reaction), therefore, the compound .B. must be an amide and .C. must be an amine. The only aromatic amine having molecular formula `C_(6)H_(7)N` is `C_(6)H_(5)NH_(2)` (aniline).
(ii) Since .C. is aniline, the amide from which is formed by must be benzamide `(C_(6)H_(5)CONH_(2))`.
`underset("Aniline (C)")(C_(6)H_(5)NH_(2)) overset(Br_(2),KOH)(larr) underset("Benzamide (B)")(C_(6)H_(5)CONH_(2))`
Thus, B is benzamide.
(iii) Since B is formed from A with aqueous ammonia and heating, therefore, compound ‘A’ must be benzoic acid.
`underset("Benzoic (A)")(C_(6)H_(5)COOH underset("Heat")overset(aq. NH_(3))(to) underset("Benzamide (B)")(C_(6)H_(5).CONH_(2))`
Thus, A = `C_(6)H_(5)COOH`, B = `C_(6)H_(5)CONH_(2)`, C = `C_(6)H_(5)NH_(2)`.
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