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NaOH
Unhindered, Strong Base (H2O = 16 > 12), Strong Nucleophile (O- and unhindered)
H2O
Unhindered, Weak Base (H3O + = -2.5 < 12), Weak Nucleophile (positive)
Alcohols (CH3OH), (CH3CH2OH)
Unhindered, Weak Base (OH+ = -2.5 < 12), Weak Nucleophile (positive O)
CH3CH2ONa
Unhindered, Strong Base (when it gains a proton, the negative on the oxygen turns neutral, and neutral O = pka 16 > 12), Strong Nucleophile (O- and unhindered)
NaH
Unhindered, Strong Base (MEMORIZE - know that CA has a high pKa), Strong Nucleophile (negative charge on Hydrogen)
NaNH2
Unhindered, Strong Base (neutral N = 38), Strong Nucleophile (negative N, unhind)
NH3(1)
unhindered, Weak Base (Positive N = 10 < 12), Weak Nucleophile (neutral N)
NaSH
(memorized), Unhindered, Strong Base, Strong Nucleophile (negative S, unhind)
(CH3)3COH
Hindered! (tert-butyl), Weak Base (O+= -2.5 < 12), Weak Nucleophile (hindered)
(CH3)3COK
Hindered! (tert-butyl), Strong Base (neutral O = 16 >12), Weak Nucleophile (hindered)
LDA LiN(i-Pr)2
Hindered! (LDA), Strong Base (neutral N = 38 > 12), Weak Nucleophile (hindered)
CH3CO2Na
(memorize) CARBOXYLATE: Unhindered, WEAK base, Strong Nucleophile
CH3CO2H
Unhindered, Weak Base (Positive O = -2.5 < 12), Weak Nucleophile (neutral O)
KCN
unhindered, Weak Base (MEMORIZE), Strong Nucleophile (negative, unhind)
NaCCH
Unhindered, Strong Base (MEMORIZE), Strong Nucleophile (negative C, unhind)