JEE Advanced levelSingle correct optionDifficulty 3 of 3hc032
(Z)-But-2-ene is (i) treated with cold dilute alkaline KMnOX4 to give the diol P, and (ii) treated with BrX2 in CClX4 to give the dibromide Q. Which pair is correct?
AP is racemic butane-2,3-diol and Q is meso-2,3-dibromobutane
BP is meso-butane-2,3-diol and Q is meso-2,3-dibromobutane
CP is meso-butane-2,3-diol and Q is a racemic mixture of (2R,3R)- and (2S,3S)-2,3-dibromobutane
DP is racemic butane-2,3-diol and Q is a racemic mixture of 2,3-dibromobutane
Answer: C
Cold KMnOX4 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.