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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro107

tert-Butyl cyclohexyl ketone, ( = cyclohexyl), is treated with mCPBA. The product is then reduced with followed by . The two alcohols obtained are

  1. Acyclohexyl(tert-butyl)methanol only
  2. Bcyclohexanol and 2,2-dimethylpropan-1-ol
  3. Ccyclohexanecarboxylic acid and 2-methylpropan-2-ol
  4. Dcyclohexylmethanol and 2-methylpropan-2-ol

Answer: D

The tertiary tert-butyl group migrates in preference to the secondary cyclohexyl group, giving the ester (tert-butyl cyclohexanecarboxylate). cleaves an ester into two alcohols: the acyl part becomes cyclohexylmethanol, and the alkoxy part gives 2-methylpropan-2-ol.
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