Accedi

This lesson delves into the aldol condensation catalyzed by bases, where aldols undergo dehydration to enals. As shown in Figure 1, the β-hydroxy aldehyde formed in a base-catalyzed aldol addition reaction dehydrates on heating to yield an unsaturated carbonyl product, which is commonly referred to as an enal.

Figure1

Figure 1. The dehydration of a β-hydroxy aldehyde to an enal.

This process follows a two-step mechanism, as depicted in Figure 2. Here, the base first deprotonates the mildly acidic hydrogen at the α carbon to form an enolate ion intermediate. Subsequently, the hydroxide ion leaves via an E1cB elimination reaction to generate an enal as the final product. The trans stereoisomer of the enal is obtained as the major product.

Figure2

Figure 2. The base-catalyzed aldol condensation mechanism for dehydration of aldol to enals.

Tags

Aldol CondensationDehydrationEnalEnolate IonE1cB EliminationUnsaturated Carbonylhydroxy AldehydeBase CatalysiscarbonTrans Stereoisomer

Dal capitolo 15:

article

Now Playing

15.17 : Dehydration of Aldols to Enals: Base-Catalyzed Aldol Condensation

α-Carbon Chemistry: Enols, Enolates, and Enamines

5.1K Visualizzazioni

article

15.1 : Reattività degli Enoli

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.9K Visualizzazioni

article

15.2 : Reattività degli ioni enolato

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.4K Visualizzazioni

article

15.3 : Tipi di enoli ed enolati

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.4K Visualizzazioni

article

15.4 : Convenzioni del Meccanismo Enolato

α-Carbon Chemistry: Enols, Enolates, and Enamines

1.9K Visualizzazioni

article

15.5 : Formazione regioselettiva di enolati

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.5K Visualizzazioni

article

15.6 : Effetti stereochimici dell'enolizzazione

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.0K Visualizzazioni

article

15.7 : α-alogenazione catalizzata da acido di aldeidi e chetoni

α-Carbon Chemistry: Enols, Enolates, and Enamines

3.5K Visualizzazioni

article

15.8 : α-alogenazione di aldeidi e chetoni promossa da basi

α-Carbon Chemistry: Enols, Enolates, and Enamines

3.3K Visualizzazioni

article

15.9 : Alogenazione multipla di metilchetoni: reazione di aloformio

α-Carbon Chemistry: Enols, Enolates, and Enamines

1.9K Visualizzazioni

article

15.10 : α-alogenazione dei derivati dell'acido carbossilico: panoramica

α-Carbon Chemistry: Enols, Enolates, and Enamines

3.2K Visualizzazioni

article

15.11 : α-Bromurazione degli acidi carbossilici: reazione di Hell-Volhard-Zelinski

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.9K Visualizzazioni

article

15.12 : Reazioni dei composti α-alocarbonilici: sostituzione nucleofila

α-Carbon Chemistry: Enols, Enolates, and Enamines

3.1K Visualizzazioni

article

15.13 : Nitrosazione degli Enoli

α-Carbon Chemistry: Enols, Enolates, and Enamines

2.4K Visualizzazioni

article

15.14 : Formazione del legame C-C: Panoramica sulla condensazione aldolica

α-Carbon Chemistry: Enols, Enolates, and Enamines

13.3K Visualizzazioni

See More

JoVE Logo

Riservatezza

Condizioni di utilizzo

Politiche

Ricerca

Didattica

CHI SIAMO

Copyright © 2025 MyJoVE Corporation. Tutti i diritti riservati