| |
poor nucleophiles in protic solvents catalyzed by acids |
good nucleophiles in aprotic solvents |
strong bases |
strong sterically hindered bases |
| methyl |
very slow or no reaction |
SN2 |
SN2 |
SN2 |
| primary |
rearrangements |
SN2 |
SN2 |
E2 |
| primary hindered |
rearrangements |
SN2 |
E2 |
E2 |
| secondary |
SN1, E1 with heat (Saytzeff) |
SN2 |
E2 (Saytzeff) |
E2 (Hofmann) |
| tertiary |
SN1, E1 with heat (Saytzeff) |
SN1, E1 with heat (Saytzeff) |
E2 (Saytzeff) |
E2 (Hofmann) |