hard · MCAT

During a laboratory synthesis, a chemist attempts to perform an S_N2 reaction on a tertiary alkyl halide using a strong nucleophile in a polar aprotic solvent.

Which of the following is the most likely outcome of this experiment?

  1. No reaction will occur because polar aprotic solvents stabilize the tertiary carbocation.
  2. An E2 elimination reaction will predominate, forming an alkene.
  3. The reaction will proceed with inversion of configuration at the stereocenter.
  4. The reaction will follow S_N1 kinetics, producing a racemic mixture.

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