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.

Explanation

`underset("compound A")underset("(optically active )")(C_(6)H_(10)O)+2H_(2) overset("Catalyst")rarr underset("(optically inactive)")underset("compound B")(C_(6)H_(14)O) overset(CrO_(3))rarr"No reaction"`
Compound A is unsaturated monohydric alcohol and it has either two `C=C` bonds or one triple bond .
Compound A is optically active and after hydrogenation optically inactive compound .B. is obtained which is not oxidised with `CrO_(3)`. Hence, in it-OH group is attached with tertiary C -atom ie, it is a tertiary alcohol.
Thus, the possible structure of A is gives as below:
`underset(" "CH_(2)-CH_(3))underset(|)overset(OH)overset(|)overset(**)(" "CH_(3)-C-C-=CH)` Here, `.^(**)C` is an asymmetric C-atom and shows optical activity.
`underset("(optical active)")underset("compound A") underset(|)overset(OH)overset(|)overset(**)(" "CH_(3)-C-C-=CH+2H_(2)) overset("Catalyst")rarr underset("(optical inactive)")underset("compound B") underset(|)overset(OH)overset(|)overset(**)(" "CH_(3)-C-CH_(2)-CH_(3))`