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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro108

1-Methylcyclohexene oxide (the epoxide of 1-methylcyclohexene) is opened in three ways. Which statements are correct?

  1. A/ gives 2-methoxy-2-methylcyclohexan-1-ol (OMe on the carbon that bears the methyl).
  2. B/ gives 2-methoxy-1-methylcyclohexan-1-ol (OMe on the carbon without the methyl).
  3. CIn both cases the OH and OMe groups are trans to each other.
  4. DUnder acidic conditions methanol attacks the less substituted epoxide carbon.

Answer: A, B, C

Acid catalysis: the more substituted (tertiary) carbon bears more positive charge and is attacked, so statement 1 is true and statement 4 is false. Base catalysis: attack occurs at the less hindered secondary carbon, so statement 2 is true. Both openings are backside attacks, so the new C-O bond and the remaining C-O bond are anti, giving trans products (statement 3).
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