Question

An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C₇H₈O which on oxidation with CrO₃ gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

Answer 1

Benzaldehyde has a characteristic odour. Reaction of ‘A’ with NaOH appears to be Cannizzaro reaction which gives ‘B’ (benzyl alcohol) and ‘C’ (Sodium salt of benzoic acid). Oxidation of alcohols gives aldehydes. Sodium salt of benzoic acid on heating with soda lime given benzene (D).