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JEE Main levelSingle correct optionDifficulty 2 of 3hc266

The compound shown is oxidised with hot alkaline and then acidified. Which structure is the product?

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

Answer: D

The compound shown is p-xylene. Both methyl groups have benzylic hydrogens, so both are oxidised, and the para relationship is kept: benzene-1,4-dicarboxylic (terephthalic) acid. The mono-acid is the product of partial oxidation, and the 1,2- and 1,3-diacids come from o- and m-xylene.
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More questions on Alkene identification from ozonolysis data and side-chain oxidation of alkylbenzenes