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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx214

(R)-Butan-2-ol is treated with and pyridine to give X. X is then treated with excess hydroxide under conditions of pure SN2 to give Y. Y is

  1. A(R)-butan-2-ol
  2. B(S)-butan-2-ol
  3. Cbutan-1-ol
  4. Dracemic butan-2-ol

Answer: A

Step 1 (SOCl2/pyridine) inverts: (R)-alcohol gives (S)-2-chlorobutane. Step 2 (SN2 with OH-) inverts again: (S)-chloride gives (R)-alcohol. Two inversions return the original configuration.
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