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C-, N-, O-, charge trapped
Good Nucleophile Strong Base
OH-, OR-, NR2-, -C-=CR
Good Nucleophile Strong base
O-. C-, N-, charge delocalized
Good Nucleophile Weak Base
Bulky Atoms
T-Butoxide, LDA
-OC(CH3)3, -NC2(CH3)4
Poor Nucleophile, Strong Base
H2O, Neutral O Species, HOCH3
Bad Nu, Weak Base
Poor Nu Weak Base - 2*, 3*
Sn1/E1 Reaction
Poor Nu Weak Base - Below 2*
No reaction
Good Nu Weak Base - 3*
Sn1/E1G
Good Nu Weak Base - Below 3*
Sn2
Good Nu Strong Base - methyl/1* unhindered
Sn2
Good Nu Strong base - everything else
E2
Poor Nu Strong Base - methyl
Sn2
Poor Nu Strong Base
E2