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JEE Main levelSingle correct optionDifficulty 2 of 3ap139

Cyclohexene oxide is treated with methanol containing a catalytic amount of . The major product is

  1. A1,2-dimethoxycyclohexane
  2. Btrans-2-methoxycyclohexan-1-ol (racemic)
  3. Ccyclohexane-1,2-diol
  4. Dcis-2-methoxycyclohexan-1-ol

Answer: B

Acid protonates the epoxide oxygen, and methanol attacks from the face opposite the C-O bond, which opens the ring with inversion at that carbon (anti opening). The product has the methoxy and hydroxyl groups on opposite faces, i.e. trans, and forms as a racemic pair.
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