Lesson35 - The Aldol Addition Reaction In this reaction two molecules of an aldehyde or ketone combine to produce a-hydroxycarbonyl One molecule

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The Aldol Addition Reaction In this reaction, two molecules of an _________________ combine to produce a β -hydroxycarbonyl . One molecule serves as the nucleophile (enol or enolate) and the other is the electrophile which undergoes carbonyl addition. The reaction is acid or base catalyzed. aldehyde or ketone New C–C bond α β
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Base-Catalyzed Aldol Addition H C O CH 2 H H C O CH 3 + H C O CH 2 H C OH CH 3 H C O CH 2 Na OH H C O CH 2 enolate anion H C O CH 2 H C O CH 3 + H OH a β -hydroxyaldehyde H O H OH H C O CH 3 OH [pt] [pt] [Ad N ] Under basic conditions the intermediates bear negative charges
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Acid-Catalyzed Aldol Addition H C O CH 2 H H C O CH 3 + H C O CH 2 H C OH CH 3 H C O CH 3 H C OH CH 2 H C O CH 2 H C OH CH 3 H O H H H + H H O H H H O H H H OH H OH [pt] [Ad N ] [pt] [taut] enol Under acidic conditions the intermediates bear positive charges
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Dehydration of β -Hydroxy Carbonyl Compounds Is Common in Aldol Reactions H C O CH CH OH CH 3 H C O CH CH CH 3 H warm acid or base H C
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This note was uploaded on 01/25/2012 for the course CHEM 232 taught by Professor Miller during the Spring '08 term at University of Illinois, Urbana Champaign.

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Lesson35 - The Aldol Addition Reaction In this reaction two molecules of an aldehyde or ketone combine to produce a-hydroxycarbonyl One molecule

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