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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hc035

Which of the following statements are correct?

  1. AThe heat of hydrogenation of (E)-but-2-ene is smaller in magnitude than that of (Z)-but-2-ene
  2. BHydroboration-oxidation of 1-methylcyclohexene gives trans-2-methylcyclohexan-1-ol
  3. COxymercuration-demercuration of 3,3-dimethylbut-1-ene gives 3,3-dimethylbutan-2-ol without skeletal rearrangement
  4. DAddition of to cyclohexene in gives mainly cis-1,2-dibromocyclohexane

Answer: A, B, C

B and H add syn: B goes to and H to on the same face, so the new OH and the methyl on are trans. The mercurinium ion does not allow a carbocation rearrangement, so Markovnikov OH appears on . The E alkene is more stable, so it releases less heat on hydrogenation. Bromination is anti, giving trans-1,2-dibromocyclohexane.
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