Compound (A) with molecular formula C_(2)H_(4)O reduces Tollen's reagent. (A) on treatment with HCN gives compound (B). Compound (B) on hydrolysis with an acid gives compound ( C) with molecular formula C_(3)H_(6)O which is an optically active compound. Compound (A) on reduction with N_(2)H_(4)//C_(2)H_(5)ONa gives a hydrocarbon (D) of molecular formula C_(2)H_(6). Identify (A), (B), ( C) and (D) and explain the reactions.

Compound (A) with molecular formula C_(2)H_(4)O reduces Tollen's reage

1.	Compound (A) with molecular formula C_(2)H_(4)O reduces Tollen's reagent. (A) on treatment with HCN gives compound (B). Compound (B) on hydrolysis with an acid gives compound ( C) with molecular formula C_(3)H_(6)O which is an optically active compound. Compound (A) on reduction with N_(2)H_(4)//C_(2)H_(5)ONa gives a hydrocarbon (D) of molecular formula C_(2)H_(6). Identify (A), (B), ( C) and (D) and explain the reactions.
Answer» Solution :(i) COMPOUND (A) with molecular formula `C_(2)H_(4)O` reduces Tollen's reagent. (ii) (A) on TREATMENT with HCN gives compound (B). `underset((A))(CH_(3)CHO)+HCNtounderset((B))(CH_(3)-underset(OH)underset(\|)(CH)-CN)` (iii) Compound (B) on hydrolysis with an acid gives compound (C) with molecular formula `C_(3)H_(6)O_(3)` which is an optically active compound. `underset((B))(CH_(3)-underset(OH)underset(\|)(CH)-CN)underset(Delta)overset(H^(+)H_(2)O)tounderset((C))(CH_(3)-underset(OH)underset(\|)(CH)-COOH)` (IV) Compound (A) on reduction with `N_(2)H_(4)//C_(2)H_(5)ONa` gives a hydrocarbon (D) of molecular formula `C_(2)H_(6)`. `underset((A))(CH_(3)CHO)underset(N_(2)H_(4)//C_(2)H_(5)ONa)overset([H])tounderset((D))(CH_(3)CH_(3))`