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JEE Main levelOne or more correct optionsDifficulty 2 of 3o3086

The reaction is run at a given temperature. Which changes will increase the rate constant of this SN2 reaction?

  1. AReplacing by the weaker nucleophile acetate, under otherwise identical conditions
  2. BUsing in acetonitrile together with 18-crown-6, which complexes
  3. CChanging the solvent from DMSO to methanol
  4. DChanging the solvent from methanol to DMF

Answer: B, D

Hydrogen-bonding solvents such as methanol suppress an anionic nucleophile, so going from methanol to DMF increases the rate. A crown ether encapsulates the cation and frees the anion from ion pairing, which also increases the rate. Going from DMSO to methanol decreases the rate. Acetate is a poorer nucleophile than azide toward carbon here, so replacing azide by acetate lowers the rate.
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