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Anomalous Behaviour of Fluorine

An optically ...

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 $C r O_{3}$ 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 $C r O_{3}$ . Hence, in it $- O H$ group is attached with tertiary C-atom i.e. it is a tertiary alcohol.

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