Nucleophiles_Overview.pdf

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Department
Chemistry
Course
CHE 118A
Professor
Vahid Eskandari
Semester
Fall

Description
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: NaOCH (a3y NaOR), LiCH (any3RLi), NaOH or KOH, NaCN or KCN, NaCCR (acetylide anion), NaNH ,2NaNHR, NaNR , NaI2 LiBr, KI, NaN 3 Weak Nucleophiles – • Typically neutral molecules • Participate in SN1-type substitutions Examples: H 2, ROH, H S2 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 nuc
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