Question: An optically active compound D has the molecular formula C6H10 and shows a peak at about 3300 cm-1 in its IR spectrum. On catalytic hydrogenation

An optically active compound D has the molecular formula C6H10 and shows a peak at about 3300 cm-1 in its IR spectrum. On catalytic hydrogenation D yields E (C6H14). Compound E is optically inactive and cannot be resolved. Propose structures for D and E.

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