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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc232

The cyclic alkene shown is treated with ozone and then with . Which structure is the product?

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

Answer: D

The compound shown is 3-methylcyclopentene. The double bond lies between C1 and C2, with the methyl on C3 next to it. Cleavage and oxidation give a carboxylic acid at each end of a five-carbon chain, and the methyl sits on the carbon next to one acid group, so the product is 2-methylpentanedioic acid. The 3-methyl isomer would need the methyl on the middle carbon.
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