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JEE Advanced levelSingle correct optionDifficulty 3 of 3ro216

2-Methylpropene is treated with mCPBA, and the epoxide formed is then treated with in methanol, followed by a neutral work-up. The major product is

  1. A1-methoxy-2-methylpropan-2-ol
  2. B2-methoxy-2-methylpropan-1-ol
  3. C2-methoxy-2-methylpropane
  4. D2-methylpropane-1,2-diol

Answer: A

The first step gives 2,2-dimethyloxirane. Under basic conditions the strong nucleophile methoxide attacks by SN2 at the less hindered CH2 carbon, so oxygen remains on the tertiary carbon. The product is . Acid-catalysed methanolysis would instead give the other regioisomer.
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