Question

Compound A(C6H12O2) on reaction with LiAlH4 yielded two compounds B and C. The compound B on oxidation gave D, which on treatment with aqueous alkali and subsequent heating furnished E. E on catalytic hydrogenation gave C. D was oxidized to form F which is a monobasic carboxylic acid with molecular mass 60. Deduce the structures of A, B, C, D.

Answer 1

Molecular mass of F is 60 and it is a monobasic acid. Thus it contains two oxygen atoms. Let the formula of the acid be CnH2nO2.

CnH2nO2 = 60 12n + 2n + 32 = 60

14n = 60-32 n = 28/14 = 2

Thus F is C2H4O2 or CH3COOH (ethanoic acid). The sequence of the reaction would be-