Nucleophile & Bases

N3-

strong nucleophile, weak base

CN-

strong nucleophile, weak base

HS-

strong nucleophile, weak

base

RS-

strong nucleophile, weak base

HO-

strong nucleophile, strong base

RO-

strong nucleophile, strong base

Protonated alkyne

strong nucleophile, strong base

F-

weak nucleophile (unless it is in aprotic solvent), weak base

Cl-

strong nucleophile, weak base

Br-

strong nucleophile, weak base

I-

strong nucleophile (unless it is in aprotic solvent), weak base

R-SH

strong nucleophile, weak base

R3N

strong nucleophile, weak base

R2NH

strong nucleophile, weak base

RNH2

strong nucleophile, weak base

H2O

weak nucleophile, weak base

R-OH

weak nucleophile, weak base

COOH

weak nucleophile, weak base

tertbutyloxide

weak nucleophile, strong base

H-

weak nucleophile, strong base

HSO4-

weak nucleophile, weak base

TsO-

weak nucleophile, weak base

-NH2

strong nucleophile, strong base

R-

strong nucleophile, strong base

-NR2

strong nucleophile, strong base

DBU

strong bulky base, non-nucleophilic

DBN

strong bulky base, non-nucleophilic

LDA

strong bulky base, non-nucleophilic

Et3N

strong bulky base, non-nucleophilic

OH w/ Strong Acid

Alcohol Activation

TsCl & Pyridine

Alcohol Activation