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)