lecture 19.1

lecture 19.1 - 19-19-1Organic Organic...

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Unformatted text preview: 19-19-1Organic Organic ChemistryChemistryWilliam H. BrownWilliam H. BrownChristopher S. FooteChristopher S. FooteBrent L. IversonBrent L. Iverson19-19-2Enolate AnionsEnolate AnionsChapter 19Chapter 1919-19-3Formation of an Enolate AnionFormation of an Enolate AnionEnolate anions are formed by treating an aldehyde or ketone with basemost of the negative charge in an enolate anion is on oxygenCH3-C-HONaOHH CC-HOHH CC-HO -Na+HH2O++An enolate anion19-19-4Enolate AnionsEnolate AnionsEnolate anions are nucleophiles in SN2 reactions and carbonyl addition reactionsAn enolateanionnucleophilicsubstitutionA 1 haloalkaneor sulfonateRRRO+R'BrORRRSN2R'+BrAn enolateanionnucleophilic additionA ketoneA tetrahedral carbonyl addition intermediateRRRO+R'R'OORRROR'R'19-19-5The Aldol ReactionThe Aldol ReactionThe most important reaction of enolate anions is nucleophilic addition to the carbonyl group of another molecule of the same or different compoundalthough these reactions may be catalyzed by either acid or base, base catalysis is more common19-19-6The Aldol ReactionThe Aldol ReactionThe product of an aldol reaction isa -hydroxyaldehydeor a -hydroxyketoneCH3-C-HOCH2-C-HHONaOH3--2--+AcetaldehydeAcetaldehyde3-Hydroxybutanal(a b-hydroxyaldehyde; racemic)OCH3-C-CH3CH3-C-CH3OCH2-C-CH3OHBa(OH)2Ba(OH)233--2--333--2--3Acetone+4-Hydroxy-4-methyl-2-pentanone(a b-hydroxyketone)+Acetone19-...
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This note was uploaded on 03/30/2008 for the course CHEM 262 taught by Professor Forbes during the Spring '08 term at UNC.

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lecture 19.1 - 19-19-1Organic Organic...

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