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JEE Advanced levelSingle correct optionDifficulty 3 of 3o2211

1-Methylcyclohexene reacts with (i) in the dark with no peroxide and (ii) with peroxide. Which pair gives the constitution of the major products?

  1. A(i) 1-bromo-2-methylcyclohexane; (ii) 1-bromo-2-methylcyclohexane
  2. B(i) 1-bromo-1-methylcyclohexane; (ii) 1-bromo-1-methylcyclohexane
  3. C(i) 1-bromo-1-methylcyclohexane; (ii) 1-bromo-2-methylcyclohexane
  4. D(i) 1-bromo-2-methylcyclohexane; (ii) 1-bromo-1-methylcyclohexane

Answer: C

The ionic path goes through the tertiary cation and gives the Markovnikov tertiary bromide. In the radical path adds to the less substituted carbon to give the tertiary radical, so Br ends on the secondary carbon next to C-CH3. The product is 1-bromo-2-methylcyclohexane.
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