Nucleophilic Subsitution and Elimination Reactions

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?