Lecture18outline

Lecture18outline - I Review Enolates can react on carbon or...

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I. Review • Enolates can react on carbon or oxygen, the difference is that poor electrophiles have later transition states that reflect the stability of the carbonyl group while more reactive electrophiles like silyl chlorides react through an earlier transition state that reflects the charge density on oxygen • The aldol reaction is very useful in synthesis because it combines carbon-carbon bond formation with stereocenter generation • From a conceptual viewpoint, the aldol reaction is attractive because it combines the abilities of ketones to act as both nucleophiles and as electrophiles • Enolates can be considered as reversible nucleophiles, making aldol reactions reversible through a process called the retro aldol reaction • Because of the near enthalpic equivalence of aldol starting materials and products, variations in temperature can be used to manipulate the equilibrium (T Δ S) • Aldol reactions also proceed under acidic conditions, with enol nucleophiles and protonated aldehydes as electrophiles
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

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Lecture18outline - I Review Enolates can react on carbon or...

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