Single correct option
(R)-2-Bromobutane is treated with aqueous NaOH under conditions that favour to give an alcohol . is converted to its tosylate with -toluenesulfonyl chloride, and the tosylate is then heated with NaBr in acetone to give . is
- A. (S)-2-bromobutane
- B. racemic 2-bromobutane
- C. (R)-2-bromobutane
- D. butan-2-ol
Show answer and solution
Answer: (C) (R)-2-bromobutane
Step 1 is 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 displacement of by with a second inversion, giving (R)-2-bromobutane. Net: two inversions and one retention, so has the same configuration as the starting bromide.
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