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ENOL AND ENOLATE

By German Fernandez, 30 May, 2024

Formation of enols and enolates

Aldehydes and ketones have acidic hydrogens on the $\alpha$ carbon, which can be removed using strong bases, forming resonance-stabilized enolate ions.

Alkylation of enolate ions

Enolate ions are alkylated by attacking carbon electrophiles such as haloalkanes, epoxides, other carbonyls, etc.

Halogenation of aldehydes and ketones

The $\alpha$ position of aldehydes and ketones is halogenated through enol or enolate intermediates.

Hydrogen - Deuterium Exchange

Hydrogens located at position a of aldehydes and ketones are replaced by deuterium upon treatment with D+/D2O or DO-/D2O

Aldol condensation

Aldehydes and ketones undergo base-catalyzed condensations in which the enolate of one molecule attacks the carbonyl of another. This reaction is known as the aldol condensation.

Preparation of a,b-unsaturateds

$\alpha, \beta$-unsaturated compounds can be prepared by four types of reactions:
1. Aldol condensation
2. Oxidation of allylic alcohols with manganese dioxide
3. Halogenation of the a-position of a carbonyl followed by elimination
4. Wittig reaction

Michael and Robinson

Enolates also attack $\alpha,\beta$-unsaturated carbonyls, forming 1,5-dicarbonyl compounds that can subsequently condense via an intramolecular aldol reaction. These are known as the Michael and Robinson reactions.


To learn more........

  • Formación de Enolatos
  • Alquilación de Enolatos
  • Alquilación mediante el empleo de enaminas
  • Intercambio Hidrógeno-Deuterio
  • Isomerización vía enoles o enolatos
  • Halogenación de Carbonilos
  • Reacción del yodoformo
  • Condensación Aldólica
  • Condensación aldólica con cetonas
  • Condensación aldólica cruzada
  • Condensación aldólica intramolecular
  • Preparación de \(\alpha,\beta\)-insaturados
  • Adiciones \(\alpha,\beta\)-insaturados
  • Adición de Michael y Ciclación de Robinson
  • Retrosíntesis del producto de Robinson

Enlaces transversales de Book para ENOLES Y ENOLATOS

  • Formación de Enolatos

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