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JEE Main levelOne or more correct optionsDifficulty 2 of 3o3268

The epoxide shown is subjected to various reagents. Select all correct statements.

  1. AAqueous gives trans-cyclohexane-1,2-diol
  2. BAqueous gives cis-cyclohexane-1,2-diol
  3. C followed by work-up gives cyclohexanol
  4. DThe diol formed with aqueous is a meso compound

Answer: A, C

The compound is cyclohexene oxide. Aqueous hydroxide opens it by backside attack (anti opening) to trans-cyclohexane-1,2-diol (racemic; the trans diol is chiral). delivers hydride to a ring carbon to give cyclohexanol. Acid-catalysed hydrolysis also proceeds with backside attack and gives the trans diol, not cis, and the trans diol is not meso (it is chiral). Correct: first and third.
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