1 nucleophilic reactions involving enolate anions aldehydes, ketons and other carbonyl compounds...
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![Page 1: 1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol](https://reader036.vdocuments.site/reader036/viewer/2022062304/56649cd65503460f9499e2aa/html5/thumbnails/1.jpg)
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Nucleophilic reactions involving enolate anions
Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol tautomerization
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Nucleophilic reactions involving enolate anions
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Nucleophilic reactions involving enolate anions
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Nucleophilic reactions involving enolate anions
Enolate anionConjugated base
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Nucleophilic reactions involving enolate anions
Hydrogen Exchange
Racemization
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Nucleophilic reactions involving enolate anions
Conjugation
Enol-Form -> Keto-Form
Progesterone(female sex hormone)
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Nucleophilic reactions involving enolate anions
Halogenation
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Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
Enolate anion acting as carbanion nucleophiles in SN2 reaction
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Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
Reaction not possible with aryl halides
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Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
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Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
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Nucleophilic reactions involving enolate anions
Addition-dehydration: Aldol reaction
Carbonyl compounds reacting as electrophiles -> aldol reaction
Aldehydes are better electrophiles than ketons-> aldol reaction more favourable with aldehydes
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Nucleophilic reactions involving enolate anions
Addition-dehydration: Aldol reaction
mixed aldol reaction
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Nucleophilic reactions involving enolate anions
Addition-dehydration: Aldol reaction
Product from aldol reaction dehydrates by heating in acid or base -> α,β unsaturated carbonyl compound
Under basic conditions -> E1cb (elimination-unimolecular-conjugated base)
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Nucleophilic reactions involving enolate anions
Addition-dehydration: Aldol reaction
Intramolecular aldol reaction
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Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles: nitriles and nitromethane
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Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles: nitriles and nitromethane
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Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles: nitriles and nitromethane
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Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
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Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
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Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
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Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates
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Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates
base
More favourable with ketons and aldehydes
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Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates