As shown in Figure 1, under acidic conditions, the β-hydroxy ketone undergoes dehydration via an E1 elimination reaction to form an enone.
Figure 1. The dehydration reaction of a β-hydroxy ketone.
Figure 2 depicts the sequential processes involved in the mechanism of the reaction. Here, the acid protonates the hydroxyl group in the β-hydroxy ketone to form a hydrated hydroxyl group, which then departs to form a tertiary carbocation intermediate. Subsequently, the loss of the hydrogen atom from the α carbon yields an enone as the final product.
Figure 2. The mechanism of the dehydration reaction of a β-hydroxy ketone.
Aus Kapitel 15:
Now Playing
15.18 : Dehydration of Aldols to Enones: Acid-Catalyzed Aldol Condensation
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.0K Ansichten
15.1 : Reactivity of Enols
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.8K Ansichten
15.2 : Reactivity of Enolate Ions
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.3K Ansichten
15.3 : Types of Enols and Enolates
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.4K Ansichten
15.4 : Enolate Mechanism Conventions
α-Carbon Chemistry: Enols, Enolates, and Enamines
1.9K Ansichten
15.5 : Regioselective Formation of Enolates
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.4K Ansichten
15.6 : Stereochemical Effects of Enolization
α-Carbon Chemistry: Enols, Enolates, and Enamines
1.9K Ansichten
15.7 : Acid-Catalyzed α-Halogenation of Aldehydes and Ketones
α-Carbon Chemistry: Enols, Enolates, and Enamines
3.4K Ansichten
15.8 : Base-Promoted α-Halogenation of Aldehydes and Ketones
α-Carbon Chemistry: Enols, Enolates, and Enamines
3.2K Ansichten
15.9 : Multiple Halogenation of Methyl Ketones: Haloform Reaction
α-Carbon Chemistry: Enols, Enolates, and Enamines
1.8K Ansichten
15.10 : α-Halogenation of Carboxylic Acid Derivatives: Overview
α-Carbon Chemistry: Enols, Enolates, and Enamines
3.2K Ansichten
15.11 : α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.9K Ansichten
15.12 : Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution
α-Carbon Chemistry: Enols, Enolates, and Enamines
3.1K Ansichten
15.13 : Nitrosation of Enols
α-Carbon Chemistry: Enols, Enolates, and Enamines
2.3K Ansichten
15.14 : C–C Bond Formation: Aldol Condensation Overview
α-Carbon Chemistry: Enols, Enolates, and Enamines
13.2K Ansichten
See More
Copyright © 2025 MyJoVE Corporation. Alle Rechte vorbehalten