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JEE Main levelSingle correct optionDifficulty 2 of 3hx209

(R)-Butan-2-ol is treated with in the presence of pyridine. The main product is

  1. Abutan-1-ol
  2. B(R)-2-chlorobutane
  3. Cracemic 2-chlorobutane
  4. D(S)-2-chlorobutane

Answer: D

Pyridine takes up HCl and supplies free chloride, which attacks the chlorosulfite by SN2 from the back side, so there is inversion. The priority order is unchanged, so R becomes S.
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