登录

Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.

In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals readily can be protected from undergoing undesirable reactions. For instance, if a compound contains a ketone and an ester group, the ketone can be protected by converting it into acetal. On the other hand, the ester does not form acetal; hence it can be subjected to the desired reaction, and inthe end, the ketone can be deprotected.

Figure1

The sulfur-containing analogs of acetals are called thioacetals thatcan act as an efficient protecting group for aldehydes and ketones. The thioacetals are stable in acidic conditions. Due to this, they cannot be deprotected by acid hydrolysis. Instead, mercuric chloride in aqueous acetonitrile is used for its deprotection.

Figure2

Apart from acting as protecting groups, thioacetals also play a major role in organic synthesis, especially in reduction reactions. Thioacetals can undergo desulfurization in the presence of Raney nickel and hydrogen to form hydrocarbons.

Figure3

Tags

AcetalsThioacetalsProtecting GroupsAldehydesKetonesAcid HydrolysisSelective ReductionDesulfurizationRaney Nickel

来自章节 12:

article

Now Playing

12.14 : Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

Aldehydes and Ketones

3.8K 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

3.3K Views

article

12.5 : 醛和酮的红外和紫外-可见光谱

Aldehydes and Ketones

5.0K 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

3.3K 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

5.1K Views

article

12.13 : 醛类和酮类的保护基团:简介

Aldehydes and Ketones

6.0K Views

article

12.15 : 醛和酮与 HCN:氰醇形成概述

Aldehydes and Ketones

2.5K 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。