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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3104

A small amount of is added to a mixture of 1-chlorobutane in aqueous acetone, in which 1-chlorobutane hydrolyses only slowly. The hydrolysis becomes much faster. Select the correct statements.

  1. AIodide acts as a catalyst because it is a poorer leaving group than chloride.
  2. B1-Iodobutane is attacked by water far more easily than 1-chlorobutane because iodide is a better leaving group.
  3. CIodide is regenerated in the second step, so only a catalytic amount is needed.
  4. DIodide is a much better nucleophile than water and displaces chloride by SN2 to give 1-iodobutane.

Answer: B, C, D

Nucleophilic catalysis: replaces (fast, since iodide is a strong nucleophile) and the resulting alkyl iodide then reacts with water (fast, since iodide is an excellent leaving group). The overall effect is and iodide is recovered. The last statement is wrong: the catalyst works because iodide is a better nucleophile and a better leaving group.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group