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JEE Main levelSingle correct optionDifficulty 2 of 3o1023

The rate of the reaction is far greater in DMF than in methanol. The best explanation is that

  1. ADMF has a much higher dielectric constant than methanol, which dissociates the ions
  2. BDMF hydrogen bonds to the transition state and stabilises it
  3. Cin methanol the azide ion is hydrogen bonded and stabilised, whereas in DMF it is weakly solvated and therefore more reactive
  4. DDMF is a stronger acid than methanol and protonates the leaving group

Answer: C

Methanol donates hydrogen bonds to , lowering the reactant energy and raising the activation barrier. DMF has no O-H or N-H hydrogen to donate; it solvates the cation but leaves the anion almost unsolvated, so the nucleophile is more reactive. The dielectric constants of the two solvents are similar (about 37 and 33), so (a) is not the cause.
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