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Stereoisomerism

An organic co...

Question

An organic compound A has molecular formula $C_{12} H_{14}$ and it can be resolved into enantiomers. Compound $A$ on boiling with dilute alkaline $K M n O_{4}$ solution yield $B (C_{5} H_{10} O_{2})$ and a white crystalline substance $C$ . Compound $C$ on treatment with sodalime produced benzene. Compound B is still resolvable but decarboxylation of $B$ with sodalime renders it non-resolvable. Deduce structures of $A, B$ and $C$ .

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Solution

1-phenyl-3-methyl-pent-1-yne (compound A, optically active) reacts with dil alkaline $K M n O_{4}$ solution to form 2-methyl butanoic acid (compound B, optically active) and benzoic acid (compound C, optically inactive). Th decarboxylation of benzoic acid with sodalime gives benzene.
The decarboxylation of 2-methyl butanoic acid with sodalime gives butane which is optically inactive .

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