A sweet smelling organic compound [ A ] ( C ₉ H ₁₀ O ₂ ) undergoes acid hydrolysis to form an acid [B]. Compound [B] further reacts with Ammonia followed by heating to yield [C]. Compound [ C ] when reacted with Br ₂ in caustic potash gave compound [ D ] ( C ₆ H 7 ~N ) which gives a white precipitate with aqueous Br ₂ . Identify compounds [ A ] & [ D ]

Step-by-step solution

Compound [A] has the molecular formula C ₉ H ₁₀ O ₂ . Acid hydrolysis of [A] yields an acid [B]. Since [A] is a sweet-smelling ester, it is likely an ester of benzoic acid. Ethyl benzoate ( C ₆ H ₅ COOCH ₂ CH ₃ ) has the formula C ₉ H ₁₀ O ₂ . Hydrolysis of ethyl benzoate gives benzoic acid [B] ( C ₆ H ₅ COOH ) and ethanol. Benzoic acid reacts with ammonia to form ammonium benzoate, which upon heating yields benzamide [C] ( C ₆ H ₅ CONH ₂ ). Compound [C] (benzamide) reacts with Br ₂ in caustic potash ( KOH ), which