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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2219

1-Methylcyclohexene is treated with in water and the first-formed bromonium ion is opened by water. Which statements are correct?

  1. AWater attacks the more substituted carbon of the bromonium ion
  2. BThe intermediate does not undergo hydride shifts
  3. CAttack takes place from the face opposite to the bromine bridge
  4. DThe intermediate is a free tertiary carbocation that is attacked from either face

Answer: A, B, C

The bromonium ion has more positive charge on the tertiary carbon, so water attacks there. The attack is backside, which gives anti addition. A bridged ion is not a free cation, so there is no shift and no loss of stereospecificity.
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