登录

The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed conditions. Both the reactions involve the same steps—protonation and deprotonation— although in the reverse order.

Figure1

The base-catalyzed reaction is initiated by the abstraction of the α hydrogen from the carbonyl compound. This abstraction forms a carbanion that is stabilized by delocalization of the negative charge across the carbonyl bond.

Figure2

The resonance results in a more stable enolate ion with negative change concentrated on the oxygen atom. The enolate ion thus formed is protonated to give the enol tautomer.

In acid-catalyzed keto–enol tautomerism, the acid protonates the carbonyl oxygen to form an oxonium ion intermediate. The oxonium ion undergoes resonance stabilization by moving the π electrons from the C=O bond towards the protonated oxygen. The α hydrogen is then deprotonated to form the enol tautomer.

Figure3

Tags
Keto enol TautomerismTautomersTautomerizationAcid catalyzed ReactionBase catalyzed ReactionProtonationDeprotonationCarbanionEnolate IonResonance StabilizationOxonium IonCarbonyl CompoundNegative ChargeEnol Tautomer

来自章节 12:

article

Now Playing

12.25 : Keto–Enol Tautomerism: Mechanism

Aldehydes and Ketones

4.8K Views

article

12.1 : 醛和酮的结构

Aldehydes and Ketones

7.5K Views

article

12.2 : IUPAC 醛类命名法

Aldehydes and Ketones

5.1K Views

article

12.3 : IUPAC 酮的命名法

Aldehydes and Ketones

5.2K Views

article

12.4 : 醛类和酮类的俗名

Aldehydes and Ketones

3.2K Views

article

12.5 : 醛和酮的红外和紫外-可见光谱

Aldehydes and Ketones

4.9K Views

article

12.6 : 醛和酮的 NMR 波谱和质谱

Aldehydes and Ketones

3.5K Views

article

12.7 : 从醇、烯烃和炔烃制备醛和酮

Aldehydes and Ketones

3.2K Views

article

12.8 : 从腈和羧酸制备醛和酮

Aldehydes and Ketones

3.2K Views

article

12.9 : 从羧酸衍生物制备醛和酮

Aldehydes and Ketones

2.4K Views

article

12.10 : 羰基的亲核加成:一般机制

Aldehydes and Ketones

4.5K Views

article

12.11 : 醛和酮与水:水合物的形成

Aldehydes and Ketones

2.9K Views

article

12.12 : 醛类和酮类与醇类:半缩醛形成

Aldehydes and Ketones

5.0K Views

article

12.13 : 醛类和酮类的保护基团:简介

Aldehydes and Ketones

5.8K Views

article

12.14 : 缩醛和硫代缩醛作为醛和酮的保护基团

Aldehydes and Ketones

3.8K Views

See More

JoVE Logo

政策

使用条款

隐私

科研

教育

关于 JoVE

版权所属 © 2025 MyJoVE 公司版权所有,本公司不涉及任何医疗业务和医疗服务。