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An optically active alcohol A (C(6)H(10)...

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.

Text Solution

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`underset("(Optically active)") (C_(6)H_(10)O(A) ) overset(2H_(2))rarr B underset(CrO_(3))overset((O))rarr ` resists oxidation
Clearly, A has `a-C-=C-` bond and B should be a `3^(@)` alcohol as they resist oxidation.
Now visualise the structure of A keeping in mind a chiral central ( optically active).
A is : `CH_(3)CH_(2)-underset(CH_(3))underset(|)overset(OH)overset("|"**)C-=CHoverset(2H_(2))rarrCH_(2)CH_(3)-underset("Optically inactive")underset(CH_(3))underset(|)overset(OH)overset(|)C-CH_(2)CH_(3)` ( `**`:chiral Centre)
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