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JEE Advanced levelSingle correct optionDifficulty 3 of 3hx067

(R)-2-Bromobutane reacts with in dry acetone to give , and reacts with sodium ethanoate to give . Assume each step is a single clean SN2 reaction with inversion. The product is

  1. A(S)-butan-2-yl ethanoate
  2. Bracemic butan-2-yl ethanoate
  3. C(R)-butan-2-yl ethanoate
  4. Dbut-2-ene

Answer: C

Step 1 gives (S)-2-iodobutane, since the priorities keep the same ranking pattern as for Br and inversion changes R to S. In step 2 the oxygen of the ethanoate group again has the highest priority, followed by , and a second inversion converts S back to R. Two inversions give net retention of the spatial arrangement, so is (R)-butan-2-yl ethanoate.
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