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JEE Main levelSingle correct optionDifficulty 2 of 3o3072

-2-Bromobutane is treated with in DMSO and the reaction proceeds entirely by SN2. The product is

  1. Aracemic 2-methylbutanenitrile
  2. B-butan-2-yl isocyanide
  3. C-2-methylbutanenitrile
  4. D-2-methylbutanenitrile

Answer: C

Inversion occurs at the stereocentre. The priorities at the carbon are in the substrate and in the product (the cyano carbon has substituents (N,N,N), higher than (C,H,H)). The order is the same, so the descriptor changes from to . Cyanide in DMSO attacks through carbon, so the product is a nitrile: -2-methylbutanenitrile.
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