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Regular Claisen condensation is a base-promoted reaction involving identical esters with two α hydrogens, condensing to produce β-ketoesters. It is a nucleophilic acyl substitution reaction wherein one of the ester molecules, upon deprotonation by the base, forms a nucleophilic enolate ion, while the other molecule serves as an electrophile.

Figure1

The condensation reaction requires specific nonaqueous bases, such as alkoxide, which must be similar to the alkoxy group of the ester molecule. The use of different alkoxide ions often leads to the transesterification product. Also, the use of hydroxide bases is avoided as they result in irreversible hydrolysis of the esters to carboxylate ions.

Figure2

Tags
Claisen CondensationketoestersNucleophilic Acyl SubstitutionEnolate IonEsterTransesterificationBaseAlkoxideHydrolysisCarboxylate Ion

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15.26 : Esters to β-Ketoesters: Claisen Condensation Overview

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15.1 : Reactividad de los enoles

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15.2 : Reactividad de los iones enolato

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15.3 : Tipos de Enoles y Enolatos

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15.4 : Convenciones del mecanismo de enolato

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15.5 : Formación regioselectiva de enolatos

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15.6 : Efectos estereoquímicos de la enolización

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15.8 : α-halogenación de aldehídos y cetonas promovida por bases

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15.9 : Halogenación múltiple de metilcetonas: reacción de haloforme

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15.10 : α-Halogenación de derivados del ácido carboxílico: descripción general

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15.11 : α-bromación de ácidos carboxílicos: reacción Hell-Volhard-Zelinski

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15.12 : Reacciones de compuestos α-halocarbonílicos: sustitución nucleofílica

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15.13 : Nitrosación de enoles

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15.14 : Formación de enlaces C-C: descripción general de la condensación aldólica

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