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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3212

(2R,3R)-2,3-Dimethyloxirane reacts with in aqueous solution (followed by protonation). Azide attacks one ring carbon by SN2. The product is

  1. A(2S,3R)-3-azidobutan-2-ol
  2. B(2S,3S)-3-azidobutan-2-ol
  3. C(2R,3S)-3-azidobutan-2-ol
  4. D(2R,3R)-3-azidobutan-2-ol

Answer: C

Attack at either carbon gives the same compound because the epoxide has symmetry. The carbon attacked by azide is inverted, and its priority order (N or O the other stereocentre H) is unchanged, so its label changes from R to S. The carbon that keeps the oxygen is untouched and stays R. This gives the C-2 (OH) = R, C-3 (N3) = S product.
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