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Question: Answered & Verified by Expert
Assertion : Rate of hydrolysis of methyl chloride to methanol is higher in DMF than in water.
Reason : Hydrolysis of methyl chloride follows second order kinetics.
ChemistryHaloalkanes and HaloarenesAIIMSAIIMS 2005
Options:
  • A If both assertion and reason are true and reason is the correct explanation of assertion
  • B If both assertion and reason are true but reason is not the correct explanation of assertion
  • C If assertion is true but reason is false
  • D If both assertion and reason are false.
Solution:
1712 Upvotes Verified Answer
The correct answer is: If both assertion and reason are true and reason is the correct explanation of assertion
Hydrolysis of methyl chloride to methanol follows $\mathrm{S}_{\mathrm{N}} 2$ reaction. The rates of many $\mathrm{S}_{\mathrm{N}} 2$ reactions are affected by the solvent. Protic solvents - those that contain $-\mathrm{OH}$ or $-\mathrm{NH}$ group are generally the worst solvents for $\mathrm{S}_{\mathrm{N}}$. Polar protic solvents, (like water, alcohols and carboxylic acids), which have strong dipoles but don't have $-\mathrm{OH}$ or $-\mathrm{NH}$ groups are the best. In contrast to protic solvents, which decrease the rates of $\mathrm{S}_{\mathrm{N}} 2$ reactants by lowering the ground state energy of nucleophile, polar aprotic solvents (DMF) increase the rates of $\mathrm{S}_{\mathrm{N}} 2$ reactions by raising the ground state energy of nucleophile.

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