I would presume soft nucleophiles as resonance increases the energy of the HOMO and therefore they favour SN2 over E2?

  • $\begingroup$ Well, many properties like nucleophilicity are expressed while comparing it to another chemical species'. Creating an absolute scale of nucleophilicity only relies on our current knowledge of the "poorest nucleophiles" and the "best nucleophiles" $\endgroup$ – SteffX Jan 5 '19 at 13:57
  • $\begingroup$ Preference of SN2 over E2 is controlled by basicity and solvent. Stronger bases shift preference toward E2. Protic solvents favor E2; polar aprotic solvents favor SN2. $\endgroup$ – Ben Norris Jan 5 '19 at 15:48

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.