JEE Main Chemistry question
Identify the total number of compounds from the given set (toluene, propylbenzene, cumene, a cyclic alkene, and two further substituted-benzene structures, one bearing a tertiary benzylic carbon with no benzylic H) which will yield a monocarboxylic acid on oxidation with KMnO₄ in acidic medium.
Answer: 3
Solution
Hot acidic KMnO₄ oxidizes any benzylic side chain possessing at least one benzylic C–H all the way back to a single –COOH on the ring (regardless of the original chain length), giving a monocarboxylic (benzoic-type) acid; a side chain with NO benzylic hydrogen (a fully substituted benzylic carbon, e.g., a
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