medium · MCAT chem-phys

A student compares the S_N1 and S_N2 mechanisms in organic chemistry.

Which of the following conditions most favors the S_N2 pathway for a substitution reaction?

  1. A primary substrate in a polar aprotic solvent with a strong nucleophile.
  2. A tertiary substrate in a polar protic solvent with a weak nucleophile.
  3. A primary substrate in a polar protic solvent with a sterically hindered base.
  4. A secondary substrate at high temperatures in a nonpolar solvent.

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