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JEE Main levelSingle correct optionDifficulty 2 of 3ro083

cis-Cyclohexane-1,2-diol and trans-cyclohexane-1,2-diol are each treated with in benzene under identical conditions. Which statement is correct?

  1. AThe trans diol reacts faster because the OH groups are further apart.
  2. BNeither reacts because the diol is in a ring.
  3. CBoth react at the same rate.
  4. DThe cis diol reacts faster because it can form a cyclic lead ester.

Answer: D

The Criegee mechanism needs a cyclic lead(IV) diester. The cis diol (axial-equatorial) can span the two oxygens to form the five-membered ring easily. The diequatorial trans diol (or its diaxial form) cannot, so it reacts much more slowly.
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