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JEE Main levelSingle correct optionDifficulty 2 of 3hx041

(S)-2-Bromo-1-chloropropane, , reacts with in DMSO by an reaction in which only the C-Br bond reacts. The product, 3-chloro-2-methylpropanenitrile, is formed with

  1. Aretention of the spatial arrangement, and it is the (S) isomer
  2. Binversion of the spatial arrangement, and it is the (R) isomer
  3. Cinversion of the spatial arrangement, and it is the (S) isomer
  4. Dretention of the spatial arrangement, and it is the (R) isomer

Answer: C

inverts the spatial arrangement. In the substrate the priorities are . In the product (Cl on carbon) outranks (N,N,N), so the order becomes : two groups swap ranks. The swap and the inversion cancel, so the label stays (S).
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