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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx228

The bromide shown is treated first with in dry acetone (SN2), and the iodide so formed is then treated with in DMSO (SN2). Which structure is the final product?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

Each SN2 step inverts the stereocentre. Two inversions return the original spatial arrangement (net retention): (R)-2-bromobutane gives (S)-2-iodobutane, which gives (R)-2-methylbutanenitrile (CN attacks through carbon, so a nitrile, not an isocyanide). The enantiomeric nitrile would need an odd number of inversions, and the iodide is only the intermediate.
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