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Synthesis of Phenols II

A monobasic a...

Question

A monobasic acid A has neutralization equivalent 116 and does not decolorize Bayer's regent. Also, A is enantiomeric. A on treatment with $B r_{2} / r e d$ phosphorus produces B which is still resolvable. B on dehydrobromination produced C which shows stereoisomerism C on decarboxylation produced. D which does not show stereoisomerism. Deduce structures of A, B, C, and D.

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Solution

$P B r_{3}$ will attach the $B r$ at the suitable substitute $H$ of compound $A$ .
In the presence of alc. $K O H$ dehydrohalogenation will occur and form the product $C$ , it is showing stereoisomerism i.e. cis and trans.
After decarboxylation final product $D$ will form.

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