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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx213

(R)-2-Bromo-1-methoxypropane, , reacts with in DMSO by a pure SN2 mechanism at the stereocentre. The product is (3-methoxy-2-methylpropanenitrile). Its CIP label is

  1. AR, because the spatial inversion is offset by a change in priority order
  2. BS, because SN2 always changes R to S
  3. Cracemic
  4. DS, because retention occurs

Answer: A

In the substrate the order is Br > > > H. In the product, (O,H,H) outranks (N,N,N), so the order is > > > H. The entering group takes second rank where Br was first, which reverses the effect of geometric inversion, so the label remains R.
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