MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN1 mechanism, rate, stereochemistry, rearrangement
JEE Main levelSingle correct optionDifficulty 2 of 3o3021

Tert-butyl chloride is solvolysed in aqueous acetone containing 0.10 M (a good nucleophile). Which statement is correct?

  1. AThe rate doubles because azide takes part in the slow step
  2. BOnly is formed, since azide is more nucleophilic than water
  3. CNo azide product is formed because the cation reacts only with the solvent
  4. DThe substrate disappears at almost the same rate as without azide, but some is formed besides the alcohol

Answer: D

The slow ionisation step does not involve the nucleophile, so the rate of disappearance of the chloride is (to a good approximation) unaffected by azide. The cation is intercepted in a fast second step by whichever nucleophile is available, so both azide (present at 0.10 M) and the solvent give products, and a mixture of and results.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 mechanism, rate, stereochemistry, rearrangement
Previous questionNext question

More questions on SN1 mechanism, rate, stereochemistry, rearrangement