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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro110

A tertiary alcohol X, , containing a six-membered carbocycle, is unaffected by Jones reagent. Heating X with dilute gives the more substituted alkene Y. Y is treated with mCPBA, and the product Z is heated with dilute aqueous acid. The final product is

  1. A2-methylcyclohexanone
  2. Bcyclohexane-1,2-diol
  3. Ctrans-1-methylcyclohexane-1,2-diol
  4. Dcis-1-methylcyclohexane-1,2-diol

Answer: C

A C7 tertiary alcohol with a six-membered ring is 1-methylcyclohexanol. It dehydrates (Zaitsev) to 1-methylcyclohexene (Y), which gives its epoxide Z with mCPBA. Acidic hydrolysis opens the epoxide by anti attack of water, giving the trans diol, trans-1-methylcyclohexane-1,2-diol.
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