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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3217

Cyclohexene oxide is treated with different reagents. Which products are correctly stated?

  1. Awith : racemic trans-cyclohexane-1,2-diol
  2. Bwith in water: racemic trans-2-azidocyclohexan-1-ol
  3. Cwith in water: cis-2-hydroxycyclohexane-1-carbonitrile
  4. Dwith , then water: cyclohexanol

Answer: A, B, D

Nucleophiles open the epoxide by backside attack, so the new group and the OH are always trans on the ring. Water and azide therefore give trans products, and the achiral epoxide gives racemates. Hydride opens the ring and removes the second substituent, leaving cyclohexanol. Cyanide also gives the trans, not the cis, hydroxynitrile.
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