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JEE Main levelSingle correct optionDifficulty 2 of 3ap027

(R)-Butan-2-ol is treated with in the presence of pyridine (the reaction proceeds by SN2 with inversion of the geometry at the stereocentre). The product is

  1. A(R)-2-chlorobutane
  2. B(S)-2-chlorobutane
  3. Cracemic 2-chlorobutane
  4. D1-chlorobutane

Answer: B

Pyridine converts the intermediate alkyl chlorosulphite to a free chloride ion, which attacks from the back side. The priority order (heteroatom > ethyl > methyl > H) is the same in the alcohol and the chloride, so inversion of geometry changes R to S. The product is (S)-2-chlorobutane.
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