SINHA IIT CHEMISTRY

Strong Nucleophiles –
Usually anions with a full negative charge ( recognizable by the presence of sodium, lithium or potassium ions.) • Participate in SN2-type substitutions Examples: NaOCH3 , LiCH3 , NaOH or KOH, NaCN or KCN, NaCCR , NaNH2, NaNHR, NaNR2, NaI, KI, NaN 3 •

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

Strong Bases –

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
• Usually anions that are very sterically hindered, preventing them from attacking as nucleophiles • Participate in E2 ONLY Examples: Tert-butyl Lithium : tBuLi PotassiumTert-butoxide : KOtBu Lithium Diisopropylamide : LDA ( LiN(CH(CH3)2)2)

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SI C N H I H E IT A M IS TR Y

Usually anions with a full negative charge ( recognizable by the presence of sodium, lithium or potassium ions) • 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 , LiCH3 , NaOH or KOH, NaCN or KCN, NaCCR , NaNH2, NaNHR, NaNR2