MolSynapsequestion bank
MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / SN1 vs SN2: substrate, nucleophile, solvent, leaving group
JEE Main levelSingle correct optionDifficulty 2 of 3o3026

Assertion (A): solvolyses much faster than in 80% aqueous ethanol. Reason (R): Nucleophilic approach to the tertiary carbon is less hindered than approach to the secondary carbon.

  1. ABoth A and R are true, and R is the correct explanation of A
  2. BBoth A and R are true, but R is not the correct explanation of A
  3. CA is true but R is false
  4. DA is false but R is true

Answer: C

A is true: the tertiary halide gives the more stable tertiary carbocation (inductive effect and hyperconjugation), lowering the ionisation barrier. R is false: the tertiary carbon is more crowded, not less, and ease of approach is not the factor in a slow ionisation step.
Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on SN1 vs SN2: substrate, nucleophile, solvent, leaving group

More questions on SN1 vs SN2: substrate, nucleophile, solvent, leaving group