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JEE Main levelSingle correct optionDifficulty 2 of 3hc267

The compound shown has a branched side chain. It is heated with hot alkaline and then acidified. Which structure is the product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: A

The compound shown is isopropylbenzene (cumene). It has one benzylic hydrogen, which is enough for side-chain oxidation. The side chain is oxidised completely to the carboxyl group with loss of the other carbons, so benzoic acid forms. Acetophenone would be an incomplete oxidation product.
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