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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro260

The cis diol shown is cleaved with excess periodic acid, and the product is then stirred with aqueous and heated, which causes an intramolecular aldol condensation. Which structure is the final product?

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

Answer: B

The compound is cis-1,2-dimethylcyclohexane-1,2-diol. cleaves the ring C1-C2 bond to give the diketone octane-2,7-dione. With base, the enolate formed at C3 attacks the C7 carbonyl, closing a five-membered ring (C3-C4-C5-C6-C7), and dehydration gives 1-acetyl-2-methylcyclopentene. Attack from the C1 methyl would give a seven-membered ring, which is less favourable, and the aldol adduct without loss of water is not the condensation product.
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