JEE Main Chemistry question
An ester (A), C₁₁H₁₄O₂, was treated with LiAlH₄ to give compound (B), C₉H₁₂O, and (C), C₂H₆O. (B) on slight heating with an acid forms (D), C₉H₁₀. Compound (D) on vigorous oxidation with KMnO₄ gives terephthalic acid. The compound (A) is
Answer: (A)
Solution
LiAlH₄ reduces ester (A) to two alcohols: (C), C₂H₆O, is ethanol (so A is an ethyl ester), and (B), C₉H₁₂O, is the alcohol from the acyl portion. (B) dehydrates on heating with acid to (D), C₉H₁₀ (loss of H₂O), which on vigorous oxidation gives terephthalic acid — meaning (D) has a para-disubstituted benzene ring,
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