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 C_nH_2nO₂.

C_nH_2nO₂ = 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-