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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o2050

1-Methylcyclohexene is treated with different reagents. For which reagents does the major product contain two stereocentres (formed as a racemate)?

  1. A, then
  2. B in
  3. Cdilute in water
  4. D in the dark

Answer: A, B

Hydroboration-oxidation gives trans-2-methylcyclohexanol (C-1 and C-2 are stereocentres). Bromine gives 1,2-dibromo-1-methylcyclohexane (C-1 and C-2 are stereocentres). Acid hydration gives 1-methylcyclohexanol and HBr gives 1-bromo-1-methylcyclohexane, which have no stereocentre.
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