good nucleophile/strong base
RO- (ex. CH3CH2O-)
good nucleophile/strong base
-OH
good nucleophile/strong base
-NH2
good nucleophile/poor base
I-
good nucleophile/poor base
-SH
good nucleophile/poor base
RS-
good nucleophile/poor base
CN-
good nucleophile/poor base
N3-
good nucleophile/poor base
Br-
good nucleophile/weaker base
Cl-
good nucleophile/weaker base
NH3
good nucleophile/weaker base
F-
good nucleophile/weaker base
RCO2-
poor nucleophile/good base
bulky oxides (ex. RO- when R is tertiary)
poor nucleophile/poor base
H2O
poor nucleophile/poor base
ROH
poor nucleophile/poor base
R-COOH
Sn2
strong n/strong b w/ methyl
Sn2
strong n/strong b primary
E2
strong n/strong b secondary
E2
strong n/strong b tertiary
Sn2
strong n/weak b w/ methyl
Sn2
strong n/weak b primary
Sn2
strong n/weak b secondary
no reaction
strong n/weak b tertiary
no reaction
weak n/strong b w/ methyl
E2
weak n/strong b primary
E2
weak n/strong b secondary
E2
weak n/strong b tertiary
no reaction
weak n/weak b w/ methyl
no reaction
weak n/weak b primary
Sn1/E1
weak n/weak b secondary
Sn1/E1
weak n/weak b tertiary
alcohol
What type of compound has an -OH bond?
thiol
What type of compound has an -SH bond?
ether
What type of compound has an R-O-R bond?
sulfide
What type of compound has an R-S-R bond?