SN1 / SN2 / E1 / E2 Cheat Sheet

Weak base, Weak base, Strong base, Strong base,

poor nucleophile good nucleophile unhindered hindered
(e.g. H2O, ROH) (e.g. I–, RS–) (e.g. RO–) (e.g. t-BuO–, i-Pr2N–)
1° (not allylic or benzylic) SN2 SN2 SN2/E2 E2
2° (not allylic or benzylic) SN1/E1 SN2 SN2/E2 E2
3° (not allylic or benzylic) SN1/E1 SN1/E1 SN1/E1/E2 E1/E2
1°/2° allylic or benzylic SN1/E1 SN2 SN1/SN2/E1/E2 E1/E2
3° allylic or benzylic SN1/E1 SN1/E1 SN1/E1/E2 E1/E2

 Watch out for rearrangements of carbocation intermediates in SN1 or E1 reactions (if the
rearrangement product is more stable than initial carbocation, the rearrangement can probably
occur).
 Also, solvent effects can favor SN1/E1 or SN2/E2 (cannot decide between SN1 and E1 or between SN2
and E2 using solvent effects).

SN1 SN2 E1 E2
Substrate Stable carbocation Minimize steric Stable carbocation Forms most
3° > 2° >> 1° crowding 3° > 2° >> 1° substituted alkene
1° > 2° >> 3° 3° > 2° > 1°
Nucleophile/Base Not important Strong nucleophile Weak base Strong base
Mechanism Carbocation Concerted, Carbocation Concerted,
intermediate no intermediate intermediate no intermediate
Stereochemistry Racemization Inversion Forms most Antiperiplanar
substituted alkene transition state
Rate Law rate = k[RX] rate = k[RX][Nu] rate = k[RX] rate = k[RX][B]
Solvent Protic Polar aprotic Protic Polar aprotic