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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3211

(R)-2-Methyloxirane is treated with aqueous NaCN (basic nucleophilic conditions). What is the product?

  1. Aa racemic mixture of 3-hydroxybutanenitrile
  2. B(S)-3-hydroxy-2-methylpropanenitrile
  3. C(R)-3-hydroxybutanenitrile
  4. D(S)-3-hydroxybutanenitrile

Answer: C

Cyanide attacks the less hindered carbon (SN2), so the stereocentre bearing O and is not touched and keeps its spatial arrangement. Its priorities are O (ring carbon, then ) H in both compounds, so the descriptor stays R. Attack at the carbon would give 3-hydroxy-2-methylpropanenitrile, but this is not the pathway.
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