Compound (A) `(C_(6)H_(12)O_(2))` on reduction with `LiAlH_(4)` yielded two compounds (B) and (C ). The compound (B) on oxidation gave (D), which on treatment with aqueous alkail and subsequent heating furnished (E ). The latter on catalytic hydrogenation gave (C ). The compound (D) was oxidised further to give (F) which was found to be a monobasic acid (molecular formula weight `= 60.0`). Deduce the structures of (A), (B), (C ), (D), and (E ).

Explanation

Proceed reverse form (F): `(R-COOH=R+45=60, R=15`, therefore `R=CH_(3)-)`

Structure of (A): Reduction of (A) with LAH produces two alcohols, so (A) must be an esiter.