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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1041

(R)-Butan-2-ol is treated with (i) (TsCl), pyridine; (ii) , DMF. The final product is

  1. Aracemic 2-bromobutane
  2. B(R)-2-bromobutane
  3. C(S)-butan-2-ol
  4. D(S)-2-bromobutane

Answer: D

Tosylation takes place on oxygen and leaves the C-O bond at the stereocentre intact (retention), converting the poor leaving group into good tosylate. Bromide then displaces tosylate by in DMF with inversion of configuration. The CIP priorities (X > ethyl > methyl > H) are in the same order for and , so inversion changes R to S.
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