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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro073

1,2-Dimethylcyclohexene is heated with hot alkaline and the mixture is acidified. The product is

  1. A7-oxooctanoic acid
  2. Bcis-1,2-dimethylcyclohexane-1,2-diol
  3. Coctane-2,7-dione
  4. Doctanedioic acid

Answer: C

Both carbons of the double bond carry two alkyl groups (no H), so each becomes a ketone on cleavage and no acid can form. The ring opens to give , octane-2,7-dione (8 carbons retained). Ketones are stable to the conditions.
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