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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2214

1-Methylcyclohexene is treated with in water to give 2-bromo-1-methylcyclohexan-1-ol. Which statements are correct?

  1. ABromine ends up on C2 and OH on the tertiary carbon C1
  2. BThe product is formed as a racemic mixture
  3. CBr and OH add to the same face of the ring
  4. DBr and OH are trans to each other

Answer: A, B, D

Water attacks the bromonium ion at the more substituted C1, so OH is tertiary and Br is on C2. Attack is anti, so Br and OH are trans. Both enantiotopic faces react equally, giving a racemate, and syn addition is not observed.
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