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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3215

1-Methylcyclohexene oxide (the epoxide of 1-methylcyclohexene) is treated with methanol containing a catalytic amount of . Which product is formed mainly?

  1. Atrans-2-methoxy-2-methylcyclohexan-1-ol (OH and OMe trans)
  2. Btrans-2-methoxy-1-methylcyclohexan-1-ol
  3. Ccis-2-methoxy-1-methylcyclohexan-1-ol
  4. Dcis-2-methoxy-2-methylcyclohexan-1-ol

Answer: A

In acid the tertiary carbon (C-1, bearing methyl) has the larger partial positive charge, so methanol attacks there. The attack is from the face opposite to the epoxide oxygen (anti opening), so OMe at C-1 is trans to the OH produced at C-2. The product is trans-2-methoxy-2-methylcyclohexan-1-ol. Under basic conditions the regiochemistry would be reversed.
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