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JEE Main levelSingle correct optionDifficulty 2 of 3o3079

The tetrabutylammonium salts of the four halide ions () are allowed to react with in dry DMF. The order of the rates of substitution is

  1. Aall four react at nearly the same rate
  2. B
  3. C
  4. D

Answer: B

DMF is polar aprotic and does not hydrogen bond to anions, and the large cation barely ion-pairs. The halides are therefore nearly 'naked' and their intrinsic nucleophilicity follows basicity: is the most reactive and the least. This is the reverse of the order in methanol.
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More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group