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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3049

Choose the correct statement(s) about the leaving group in SN1 reactions of tertiary substrates.

  1. AThe order of reactivity is .
  2. B reacts faster than because the C-F bond is more polar.
  3. CProtonating with a strong acid makes the leaving group neutral and greatly increases the rate.
  4. D is more reactive than .

Answer: A, C, D

Rate follows the stability of the departing anion: iodide > bromide > chloride, and tosylate (the anion of a strong acid, delocalised) leaves even faster than bromide, so statements 1 and 4 are true. Protonation converts into (statement 3 true). The C-F bond is the strongest C-halogen bond and fluoride the poorest halide leaving group, so statement 2 is false.
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