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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc229

The cyclic diene shown is treated with excess ozone and then with . Which structure is the only organic product?

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

Answer: C

The compound shown is cycloocta-1,5-diene. Cleaving both double bonds cuts the eight-membered ring into two identical four-carbon pieces, each ending in two carbonyl carbons. Oxidative work-up turns each aldehyde end into a carboxylic acid, so two molecules of butanedioic (succinic) acid form, which is a single compound.
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