BASE
(CH₃CH₂)₂S (diethyl sulfide)
NUCLEOPHILE
SOLVENT
SOLVOLYSIS REACTION?
Fair Nucleophiles
1-Butanol (CH₃CH₂CH₂CH₂OH)
Protic Solvent
Acetic acid (CH₃CO₂H)
Protic Solvent
Acetone (CH₃COCH₃)
Aprotic Solvent
Br⁻ (Halide)
Weak Base
CH₃⁻ (methyl anion, very strong carbanion)
Strong Base
CH₃CO₂⁻ (acetate)
Weak Base
Fair Nucleophiles
Protic Solvent
Solvolysis Reaction
CH₃OH (methanol)
Weak Base
Weak Nucleophiles
Protic Solvent
Solvolysis Reaction
CH₃S⁻ (methanethiolate)
Weak Base
CH₃S⁻ (methanethiolate)
Good Nucleophiles
Solvolysis Reaction
Very Good Nucleophiles
Cl⁻ (Halide)
Weak Base
CR₃⁻ (general carbanions)
Strong Base
Fair Nucleophiles
Solvolysis Reaction
DMF (dimethylformamide)
Aprotic Solvent
DMSO (dimethyl sulfoxide)
Aprotic Solvent
Ethanol (CH₃CH₂OH)
F⁻ (fluoride)
Protic Solvent
Weak Base
Weak Nucleophiles
Weak Base
Weak Nucleophiles
Formic acid (HCO₂H)
H₂O (water)
Protic Solvent
HMPA
Protic Solvent
Solvolysis Reaction
Aprotic Solvent
HS⁻ (Hydrosulfide ion)
Very Good Nucleophiles
I⁻ (Halide)
Weak Base
N₃⁻ (azide)
Weak Base
N₃⁻ (azide)
Very Good Nucleophiles
Solvolysis Reaction
Good Nucleophiles
NC⁻/ CN- (cyanide)
Weak Base
NH₂⁻ (amide ion)
Strong Base
NH₃ (ammonia)
Good Nucleophiles
Solvolysis Reaction
Fair Nucleophiles
OCH₃⁻/CH3O- (methoxide)
Strong Base
Good Nucleophiles
Solvolysis Reaction
OH⁻ (hydroxide)
Strong Base
Good Nucleophiles
Solvolysis Reaction
R₂N⁻ (Dialkylamide ion)
Strong Base
RO⁻ (alkoxides in general)
Strong Base
t-Butyl alcohol ((CH₃)₃COH)
tBuO⁻ (tert-butoxide)/strong & bulky
Protic Solvent
Strong Base