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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1055

Solvents are: water, DMSO, hexane, methanol. Which pair correctly names the solvent giving the fastest solvolysis of and the solvent giving the fastest reaction of with (among these four that dissolve the salt)?

  1. A: hexane; : methanol
  2. B: water; : DMSO
  3. C: DMSO; : water
  4. D: water; : methanol

Answer: B

needs strong stabilisation of an ion-pair-like transition state and of the leaving anion by hydrogen bonding, so water is best (nonpolar hexane is worst). with an anionic nucleophile needs an aprotic solvent that leaves the anion unsolvated, so DMSO beats the protic water and methanol.
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