Substitution and Elimination

Strong base, weak nucleophile

NaH

Strong base, weak nucleophile

DBN

Strong base, weak nucleophile

DBU

Strong base, weak nucleophile

OtBu

Strong base, strong nucleophile

HO-

Strong base, strong nucleophile

MeO-

Strong base, strong nucleophile

EtO-

Weak base, strong nucleophile

I-

Weak base, strong nucleophile

Br-

Weak base, strong nucleophile

Cl-

Weak base, strong nucleophile

RS-

Weak base, strong nucleophile

HS-

Weak base, strong nucleophile

RSH

Weak base, strong nucleophile

H2S

Weak base, strong nucleophile

CN-

Weak base, strong nucleophile

N3-

Weak base, strong nucleophile

Ester

Weak base, weak nucleophile

H2O

Weak base, weak nucleophile

MeOH

Weak base, weak nucleophile

EtOH

Strong base, weak nucleophile

Elimination only (E2)

Weak base, strong nucleophile

Substitution only (primary and secondary = SN2, tertiary = SN1)

Concerted reaction

one step reaction

Stepwise reaction

involves more than one step

SN2 Rate

rate = k[substrate][nucleophile]

SN1 Rate

rate = k[substrate]

Acid base chemistry

Thermodynamics

Nucleophilic attack

Kinetics/pathways