Strong Nucleophiles –

• Usually anions with a full negative charge (easily recognizable by the presence of sodium, lithium or
potassium counterions)
• Participate in SN2-type substitutions
Examples:
NaOCH3 (any NaOR), LiCH3 (any RLi), NaOH or KOH, NaCN or KCN, NaCCR (acetylide anion),
NaNH2, NaNHR, NaNR2, NaI, LiBr, KI, NaN 3

Weak Nucleophiles –
• Typically neutral molecules
• Participate in SN1-type substitutions
Examples:
H2O, ROH, H2S, RSH

Strong Bases –
• Usually anions with a full negative charge (easily recognizable by the presence of sodium, lithium or
potassium counterions)
• Participate in E2-type eliminations
• May overlap with strong nucleophile list (causing mixtures of both substitutions and eliminations to be
produced)
• Halides and the azide anion are nucleophilic but not basic – only strong nucleophiles that are not also
strong bases.
Examples:
NaOCH3 (any NaOR), LiCH3 (any RLi), NaOH or KOH, NaCN or KCN, NaCCR (acetylide anion),
NaNH2, NaNHR, NaNR2

Weak Bases –
• Typically neutral molecules
• Participate in E1-type eliminations
• Can occur concurrently with SN1 reactions since both occur under similar conditions (type of halide,
carbocation intermediate, neutral nucleophile/base)
Examples:
H2O, ROH, H2S, RSH

Strong, Non-Nucleophilic Bases (SNNB) –

• Usually anions that are very sterically hindered, preventing them from attacking as nucleophiles (thus the
phrase “non-nucleophilic”)
• Participate in E2 ONLY
Examples:
Tert-butyl Lithium : tBuLi (also written as (CH3)3CLi)
PotassiumTert-butoxide : KOtBu (also written as (KOC(CH3)3)
Lithium Diisopropylamide : LDA (acronym) (also written as LiN(CH(CH3)2)2)