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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3257

The beta-thio chloride shown (racemic) hydrolyses in water. Select all correct statements about the reaction.

  1. AA cyclic episulfonium ion is an intermediate
  2. BThe rate is higher than that of 1-chlorobutane
  3. CBoth 1-(methylthio)propan-2-ol and 2-(methylthio)propan-1-ol can form
  4. DA free primary carbocation is formed in the slow step

Answer: A, B, C

The compound is 1-chloro-2-(methylthio)propane. Sulfur displaces chloride intramolecularly to form a cyclic episulfonium ion, so the rate is higher than for 1-chlorobutane. Ionisation is the slow step and the rate is first order in substrate. Water can open the ring at either carbon, giving two isomeric hydroxy sulfides. A free primary carbocation is not required (the sulfur assists), and the rate is not second order in water.
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