Question

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 ).

Answer 1

The compound (F) has molecular mass 60.
RCOOH=R+45=60orR=15,i.e., `CH_(3)`
Hence, the compound (F) is `CH_(3)COOH`. lt is obtained by oxidation of (D). Thus, (D) is `CH_(3)CHO`. (D) is formed by oxidation of (B).
Hence, (B) is `CH_(3)CH_(2)OH`. (D) undergoes aldol condensation which subsequently forms (E) on heating.
`underset((D))(2CH_(3)CHO)toCH_(3)-underset(OH)underset(|)"CH"-CH_(2)CHOoverset("Heating")toCH_(3)CH=underset((E))(CHCHO)overset(H)tounderset((C))(CH_(3)CH_(2)CH_(2)CH_(2)OH)`
(A) is, thus an ester which forms two alcohols with `LiAlH_(4)`
`underset(or)(CH_(3)CH_(2)CH_(2)COOCH_(2)CH_(3))overset(LiAlH_(4))tounderset((C))(CH_(3)CH_(2)CH_(2)CH_(2)OH)+underset((B))(CH_(3)CH_(2)OH)`
`CH_(3)COOCH_(2)CH_(2)CH_(2)CH_(3)`