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Primary
Strong Base
Poor Nucleophile
E2
Secondary
Strong Base
Poor Nucleophile
E2
Tertiary
Strong Base
Poor Nucleophile
E2
Primary
Weak Base
Poor Nucleophile
no rxn
Secondary
Weak Base
Poor Nucleophile
Sn1 + E1
Tertiary
Weak Base
Poor Nucleophile
Sn1 + E1
Primary
Weak Base
Good Nucleophile
SN2
Secondary
Weak Base
Good Nucleophile
SN2
Tertiary
Weak Base
Good Nucleophile
SN1 (RARE)
Primary
Strong Base
Good Nucleophile
Sn2>E2
Secondary
Strong Base
Good Nucleophile
E2>SN2
Tertiary
Strong Base
Good Nucleophile
E2
CH3X
Strong Base
Weak Nucleophile
no rxn
CH3X
Strong Base
Strong Nucleophile
sn2
CH3X
Weak Base
Strong Nucleophile
sn2
CH3X
Weak Base
Weak Nucleophile
no rxn
-OC(CH3)3 (text-butoxide), DBN, DBU, LDA
bulky bases
-Oh, -OCH3, -OCH2CH3, NaOMe
small bases
-OC(CH3)3 (tert-butoxide)
strong base, weak nucleotide
DBN, DBU, LDA
Strong base, weak nucleophile
-OH
strong base, strong nucleophile
-OCH2CH3, NaOEt
strong base, strong nucleophile
-OCH3, NaOMe
strong base, strong nucleophile
-I, -Br, -Cl, -N3
weak base, strong nucleophile
-CN
weak base, strong nucleophile
-SH, -SR, -H2S, -RSH
weak base, strong nucleophile
CH3CO2- (acetate)
weak base, strong nucleophile
H2O
weak base, weak nucleophile
CH3OH (methanol)
weak base, weak nucleophile
CH3CH2OH (ethanol)
weak base, weak nucleophile