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Question

An optically active alcohol A (C6H10O) 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 CrO3 and does not show any optical activity. Deduce the structures of A and B.

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Solution

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 CrO3. Hence, in it OH group is attached with tertiary C-atom i.e. it is a tertiary alcohol.
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