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Nucleophiles Overview PDF
Nucleophiles Overview PDF
• 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