Chapter 7: Alkyl Halides
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Strong base Weak nucleophile List common reagents
• DBN • DBU • t−butO
Strong base Strong nucleophile List common reagents
• OH− • MeO− • EtO−
Weak base Strong nucleophile List common reagents
• I− • Br− • Cl− • RS− • HS− • RSH • H2S (hydrogen sulfide)
Weak base Weak nucleophile List common reagents
• H2O • MeOH • EtOH
DBN Reagent category
Strong base Weak nuclephile
DBU Reagent category
Strong base Weak nuclephile
t−butO Reagent category
Strong base Weak nucleophile
OH− Reagent category
Strong base Strong nucleophile
MeO− Reagent category
Strong base Strong nucleophile
EtO− Reagent category
Strong base Strong nucleophile
I− Reagent category
Weak base Strong nucleophile
Br− Reagent category
Weak base Strong nucleophile
Cl− Reagent category
Weak base Strong nucleophile
RS− Reagent category
Weak base Strong nucleophile
HS− Reagent category
Weak base Strong nucleophile
RSH Reagent category
Weak base Strong nucleophile
H2S Reagent category
Weak base Strong nucleophile
H2O Reagent category
Weak base Weak nucleophile
MeOH Reagent category
Weak base Weak nucleophile
EtOH Reagent category
Weak base Weak nucleophile
Primary alkyl halide treated with a S. Base/W. Nuc Expected mechanism
E2
Secondary alkyl halide treated with a S. Base/W. Nuc Expected mechanism
E2
Tertiary alkyl halide treated with a S. Base/W. Nuc Expected mechanism
E2
Primary alkyl halide treated with a S. Base/S. Nuc Expected mechanism
SN2 * major product E2 minor product