OH⁻
Strong Nucleophile
Strong Base
⁻O-R
Strong Nucleophile
CH3COO⁻
Strong Nucleophile
Weak Base
⁻O-tBut
Strong Bulky Base
Weak Nucleophile
⁻OCH3
Strong Base
Strong Nucleophile
I⁻, Br⁻, Cl⁻
Weak Base
Strong Nucleophile
Usually seen with spectator ion
⁻OCH2CH3
Strong Base
Strong Nucleophile
CH3-OH
Weak Base
Weak Nucleophile
H2O
Weak Base
Weak Nucleophile
CH3COOH
Weak Base
Weak Nucleophile
CN
Weak Base
Strong Nucleophile
N3
Weak Base
Strong Nucleophile
R-OH
Weak Base
Weak Nucleophile
DBU, DBN
Strong Bulky Base
Non-nucleophilic
HI, HBr, HCl
Strong Acid
TsOH
Strong Acid
H2SO4
Strong Acid
SOCl2 / Pyridine
Only used in Alcohol rxns
Sn2
PBr3
Only used in Alcohol rxs
Sn2
POCl3 / Pyridine
Only used in Alcohol rxns
E2