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JEE Advanced levelSingle correct optionDifficulty 3 of 3o3109

2-Bromopropane is treated separately with (i) sodium ethanethiolate in ethanol and (ii) potassium tert-butoxide in tert-butanol, each at . The major products are, respectively,

  1. A(i) and (ii)
  2. B(i) and (ii)
  3. C(i) and (ii)
  4. D(i) and (ii)

Answer: A

Thiolates are excellent nucleophiles but weak bases (thiols are far more acidic than alcohols), so with a secondary halide they give the SN2 product, the sulfide. tert-Butoxide is a strong, bulky base and a poor nucleophile, so it removes a beta proton in E2 and gives propene. The bulky ether would require SN2 by a hindered nucleophile at a secondary carbon.
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