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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2038

1-Methylcyclohexene is treated with in methanol as the solvent. The major product is

  1. Atrans-2-bromo-1-methoxy-1-methylcyclohexane
  2. Btrans-1-bromo-2-methoxy-1-methylcyclohexane
  3. Ctrans-1,2-dibromo-1-methylcyclohexane
  4. Dcis-2-bromo-1-methoxy-1-methylcyclohexane

Answer: A

The bromonium ion is opened by the solvent methanol, which is in huge excess, at the tertiary carbon (more positive charge). The attack is anti, so Br and OMe are trans. The product has OMe and on the same carbon (C-1) and Br on the adjacent secondary carbon (C-2): trans-2-bromo-1-methoxy-1-methylcyclohexane.
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