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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx055

(R)-2-Bromo-1-chloropropane, , is treated separately with in DMSO (giving A) and with in DMSO (giving B), each by pure at the C-Br bond. The labels of A (1-chloropropan-2-yl acetate) and B (3-chloro-2-methylpropanenitrile) are respectively

  1. AA is (R) and B is (S)
  2. BA is (S) and B is (S)
  3. CA is (S) and B is (R)
  4. DA is (R) and B is (R)

Answer: C

Both reactions invert the spatial arrangement. For the acetate, , the same order as the bromide (), so the label flips to (S). For the nitrile, (Cl,H,H) outranks (N,N,N), so the first two priorities swap, which cancels the effect of inversion and the label remains (R).
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