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13.10     An aromatic compound ‘A’ on treatment with aqueous ammonia and heating forms compound ‘B’ which on heating with Br_{2}  and KOH  forms a  compound ‘C’ of molecular formulaC_{6}H_{7}N.. Write the structures and IUPAC names of compounds A, B and C.

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The molecular formula of C = C_{6}H_{7}N

A\xrightarrow[aq NH_{3}]{\Delta }B

B+Br_{2}+KOH\rightarrow C(C_{6}H_{7}N) it is a Hoffmann bromamide degradation reaction so, the product should be C_{6}H_{5}NH_{2} (aniline)

So B should be benzamide (C_{6}H_{5}CONH_{2}) and A should be benzoic acid (C_{6}H_{5}COOH)

Therefore the above reaction proceeds as-

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