PrepRung

JEE Main 2021 · Chemistry · Alcohols, Phenols, Ethers and Haloalkanes · medium

(R)-2-Bromobutane is treated with aqueous NaOH under conditions that favour SN2 to give an alcohol X. X is converted to its tosylate with…

Single correct option

(R)-2-Bromobutane is treated with aqueous NaOH under conditions that favour SN2\mathrm{S_N2} to give an alcohol X\mathrm{X}. X\mathrm{X} is converted to its tosylate with pp-toluenesulfonyl chloride, and the tosylate is then heated with NaBr in acetone to give Y\mathrm{Y}. Y\mathrm{Y} is
  1. A. (S)-2-bromobutane
  2. B. racemic 2-bromobutane
  3. C. (R)-2-bromobutane
  4. D. butan-2-ol
Show answer and solution

Answer: (C) (R)-2-bromobutane

Step 1 is SN2\mathrm{S_N2} with inversion: (R)-2-bromobutane gives (S)-butan-2-ol (the priority order Br or OH >> ethyl >> methyl >> H is the same, so inversion flips the descriptor). Step 2 forms the tosylate at oxygen; the C–O bond is not broken, so the configuration is retained, giving the (S)-tosylate. Step 3 is another SN2\mathrm{S_N2} displacement of OTs−\mathrm{OTs^-} by Br−\mathrm{Br^-} with a second inversion, giving (R)-2-bromobutane. Net: two inversions and one retention, so Y\mathrm{Y} has the same configuration as the starting bromide.
Report a mistake

Original question written in the JEE Main 2021 pattern and checked twice for the correct answer. Not an official question paper. How we write and check questions · Corrections policy · Report a mistake