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JEE Advanced levelSingle correct optionDifficulty 3 of 3hc032

(Z)-But-2-ene is (i) treated with cold dilute alkaline to give the diol P, and (ii) treated with in to give the dibromide Q. Which pair is correct?

  1. AP is racemic butane-2,3-diol and Q is meso-2,3-dibromobutane
  2. BP is meso-butane-2,3-diol and Q is meso-2,3-dibromobutane
  3. CP is meso-butane-2,3-diol and Q is a racemic mixture of (2R,3R)- and (2S,3S)-2,3-dibromobutane
  4. DP is racemic butane-2,3-diol and Q is a racemic mixture of 2,3-dibromobutane

Answer: C

Cold adds two OH groups syn, and syn addition to a cis alkene gives the meso diol. Bromine adds anti through the bromonium ion, and anti addition to a cis alkene gives the racemic (R,R)/(S,S) pair.
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