Ranking Nucleophiles and Leaving Groups, Hammond's Postulate

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Some Common <strong>Nucleophiles</strong>Comparing Nucleophile Quality withPotential Energy DiagramsbetterWe said HS - thanCl - (based on electronegativity).+++E+reaction coordinate

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What Makes a Good Nucleophile?3. Not too sterically hindered.t-butoxide anionstrong base,hindered nucleophilemethoxide anionsmaller, attacksmore easilyWhat Makes a Good Nucleophile?4. Not obscured by too polar a solvent.solvent hindersnucleophile fromapproachingelectrophile.So, S N 2 reactions are usually run in medium polarity solvents;polar enough to dissolve ionic species, not so polar to cage the nucleophile.

Some Common <strong>Nucleophiles</strong>Comparing Nucleophile Quality withPotential Energy DiagramsbetterWe said HS - thanCl - (based on electronegativity).+++E+reaction coordinate

Page 1: What Makes a Good Nucleophile?+ +1.
Page 5 and 6: What Makes a Good Leaving Group?1.
Page 7: Inhibition of S N 2 by Neopentyl Gr

Ranking Nucleophiles and Leaving Groups, Hammond's Postulate

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