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Question
Compare SN1 and SN2 reaction mechanisms.
Solution
| SN1 | SN2 | |
| Rate law | Unimolecular (Substrate only) | Biomolecular (substrate and nucleophile) |
| “Big Barrier” | Carbocation stability | Steric hindrance |
| Alkyl halide (electrophile) | 3° > 2° > 1° | 1° > 2° > 3° |
| Nucleophile | Weak (generally neutral) | Strong (generally bearing a negative charge) |
| Solvent | Polar protic (e.g., alcohols) | Polar aprotic (e.g., DMSO, acetone) |
| Stereo Chemistry | Mix of retention and inversion | inversion |
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