Distinguishing Substitution and Elimination Reactions

Substrate: Me > 1° > 2° Strong Nucleophile, Polar Aprotic Solvent, Good Leaving Group

Sn2

Substrate: 3° > 2° > 1°, Strong Base, Polar Aprotic* Solvent, Good Leaving Group

E2

Substrate: 3° > 2°, Weak Nucleophile, Polar Protic Solvent, Good Leaving Group

Sn1

Substrate: 3° > 2°, Weak Nucleophile, Polar Protic Solvent, Good Leaving Group

E1

H2O

Weak Nucleophile, Weak Base

ROH

Weak Nucleophile, Weak Base

RCOOH

Weak Nucleophile, Weak Base

CN-

Strong Nucleophile, Weak Base

N3-

Strong Nucleophile, Weak Base

CI-

Strong Nucleophile, Weak Base

Br-

Strong Nucleophile, Weak Base

I-

Strong Nucleophile, Weak Base

RS-

Strong Nucleophile, Weak Base

HS-

Strong Nucleophile, Weak Base

RSH

Strong Nucleophile, Weak Base

H2S

Strong Nucleophile, Weak Base

RNH2

Strong Nucleophile, Weak Base

R3P

Strong Nucleophile, Weak Base

OH-

Strong Nucleophile, Strong Base

RO-

Strong Nucleophile, Strong Base

tBuO-

Strong, Bulky Base

DBN

Strong, Bulky Base

DBU

Strong, Bulky Base

LDA

Strong, Bulky Base

Weak Nucleophile/Weak Base Reaction(s)

Sn1 & E1

Strong Nucleophile/Weak Base Reaction(s)

Sn2

Strong Nucleophile/ Strong Base Reaction(s)

Sn2 & E2

Strong, Bulky Base Reactions

E2