SN1/SN2/E1/E2 + Protic/Aprotic Solvents

Br-

strong nuc, weak base

I-

Strong nuc, weak base

Cl-

strong nuc, weak base

Cyanide (CN-)

strong nuc, weak base

RCOO-

strong nuc, weak base

SH-

strong nuc, weak base

RS-

strong nuc, weak base

N3

strong nuc, weak base

CH3O

strong nuc, strong base

NaOEt

strong nuc, strong base

-OH

strong nuc, strong base

H-C=C (pretend that’s a triple bond)

strong nuc, strong base

t-BuOK

strong bulky

DBN

weak nuc, strong base

DBU

weak nuc, strong base

H2O

weak nuc, weak base

EtOH

weak nuc, weak base

CH3OH

weak nuc, weak base

Primary

Strong nuc, weak base

SN2

Primary

Strong nuc, strong base

SN2

Primary

Strong bulky

E2

Primary

Weak nuc, strong base

E2

Secondary

Strong nuc, weak base

SN2

Secondary

Strong nuc, strong base

E2

secondary

Weak nuc, strong base

E2

Secondary

weak nuc, weak base

SN1

Secondary

weak nuc, weak base

heat

E1

Tertiary

Strong nuc, weak base

SN1

Tertiary

Strong nuc, strong base

E2

Tertiary

Strong base

E2

Tertiary

Weak nuc, weak base

SN1

Tertiary

Weak nuc, weak base

Heat

E1

polar aprotic

acetone

polar aprotic

DMSO

Acetonitrile

polar aprotic

polar aprotic

DMF

polar aprotic

diethyl ether

polar aprotic

THF

polar aprotic

HMPA

polar protic

t-butanol

polar protic

ammonia

polar protic

acetic acid

polar protic

water