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NEET levelSingle correct optionDifficulty 1 of 3o3116

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

  1. Aracemic 2-chlorobutane
  2. B(S)-2-chlorobutane
  3. C(R)-2-chlorobutane
  4. Dbutan-2-one

Answer: B

Pyridine removes HCl and supplies free chloride ion, which attacks the alkyl chlorosulfite by SN2 with inversion. Priorities are in both compounds, so inversion changes R to S: (S)-2-chlorobutane.
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