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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3ro219

Which of the following sequences convert cyclohexene into trans-cyclohexane-1,2-diol (as the racemic mixture)?

  1. AmCPBA, then dilute aqueous
  2. B, then in water
  3. Ccyclohexene oxide with aqueous NaOH, then acidification
  4. D/, then NaOH, then dilute aqueous

Answer: A, C, D

Hydrolysis of an epoxide proceeds by backside (anti) attack, giving the trans diol. This applies to the mCPBA route, to the base opening of cyclohexene oxide, and to the bromohydrin route, which makes the epoxide before the acid opening. OsO4 adds the two OH groups on the same face and gives the cis diol.
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