Question

An optically active alcohol A `(C_(6)H_(10)O)` absorbs 2 mol of hydrogen per mole of A upon catalytic hydrogenation and gives a product B. The compound B is resistant to oxidation by `CrO_(3)` and does not show any optical activity Deduce the structures of A and B.

Answer 1

`overset(A(C_(6)H_(10)O))underset((O.A.alcohol) overset(2H_(2)//Pt)rarr underset((O.I.A.))(B)overset([O])underset(CrO_(3))rarr` Resists oxidation
i. Two DU in (A) suggests that it contains either two `(C=C)` bonds or one `(C-=C)` bond, (B) is `3^(@)` alcohol, since it resists oxidation.
ii. (A) si optically active an d(B) is O.I.A., suggesting two same groups in (B). Structire of (B) is: