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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx224

The enantiopure bromide shown reacts with in DMSO by a pure SN2 mechanism. Give the CIP descriptors of the reactant and of the nitrile product, in that order.

  1. AS, S
  2. BS, R
  3. CR, S
  4. DR, R

Answer: A

The reactant is (S)-2-bromopropan-1-ol, , with priorities , descriptor S. SN2 inverts the geometry, but in the product the priorities become (O,H,H) (N,N,N) because O outranks N at the first point of difference. The new group CN occupies the old Br position in priority rank 2 rather than 1, so the label does not change: S to S (3-hydroxy-2-methylpropanenitrile, checked with RDKit), even though the geometry is inverted.
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