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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap146

(R)-2-Methoxybutane is heated with one equivalent of under mild conditions, so that the reaction takes place by SN2 at the less hindered carbon. The products are

  1. Aracemic 2-iodobutane and methanol
  2. B(S)-2-iodobutane and methanol
  3. C(S)-butan-2-ol and iodomethane
  4. D(R)-butan-2-ol and iodomethane

Answer: D

Iodide attacks the methyl group, so the C-O bond at the stereocentre is never broken and its configuration is retained. The priorities at the stereocentre ( or > ethyl > methyl > H) are unchanged, so the product alcohol is (R)-butan-2-ol along with .
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