Iniciar sesión

Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acidreacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halidewith one less carbon. This reaction is called the Hunsdiecker reaction.

Figure1

Unlike monocarboxylic acids, ꞵ-keto acids bearing a keto group at the β position to the carboxyl group, readily undergo decarboxylation under an acid medium to form a ketone and releases carbon dioxide gas.

Figure2

Decarboxylation reaction is biologically relevant while oxidizing food materials in the tricarboxylic acid (TCA) cycle. In this cycle, oxalosuccinic acid is formed as an intermediate that bears three carboxyl groups and one carbonyl group. However, as the carbonyl group is at the ꞵ-position to only one carboxyl group, only one of the three carboxyl groups undergoes decarboxylation to produce α-ketoglutaric acid by losing CO2.

Figure3

Tags

DecarboxylationketoacidsCarboxylic AcidsHunsdiecker ReactionTCA CycleOxalosuccinic Acidketoglutaric AcidCarbon DioxideKetoneOxidation

Del capítulo 13:

article

Now Playing

13.16 : Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

Carboxylic Acids

3.1K Vistas

article

13.1 : Nomenclatura IUPAC de ácidos carboxílicos

Carboxylic Acids

8.4K Vistas

article

13.2 : Propiedades físicas de los ácidos carboxílicos

Carboxylic Acids

4.3K Vistas

article

13.3 : Acidez de los ácidos carboxílicos

Carboxylic Acids

6.4K Vistas

article

13.4 : Efectos sustitutivos sobre la acidez de los ácidos carboxílicos

Carboxylic Acids

6.4K Vistas

article

13.5 : Espectroscopía IR y UV-Vis de ácidos carboxílicos

Carboxylic Acids

3.6K Vistas

article

13.6 : RMN y espectroscopia de masas de ácidos carboxílicos

Carboxylic Acids

3.5K Vistas

article

13.7 : Preparación de ácidos carboxílicos: descripción general

Carboxylic Acids

2.4K Vistas

article

13.8 : Preparación de ácidos carboxílicos: hidrólisis de nitrilos

Carboxylic Acids

3.7K Vistas

article

13.9 : Preparación de ácidos carboxílicos: carboxilación de reactivos de Grignard

Carboxylic Acids

4.1K Vistas

article

13.10 : Reacciones de los ácidos carboxílicos: Introducción

Carboxylic Acids

2.8K Vistas

article

13.11 : Ácidos carboxílicos a ésteres: Descripción general de la esterificación catalizada por ácido (Fischer)

Carboxylic Acids

17.6K Vistas

article

13.12 : Ácidos carboxílicos a ésteres: mecanismo de esterificación catalizado por ácido (Fischer)

Carboxylic Acids

7.5K Vistas

article

13.13 : Ácidos carboxílicos a ésteres metílicos: alquilación con diazometano

Carboxylic Acids

2.0K Vistas

article

13.14 : Ácidos carboxílicos a cloruros ácidos

Carboxylic Acids

6.3K Vistas

See More

JoVE Logo

Privacidad

Condiciones de uso

Políticas

Investigación

Educación

ACERCA DE JoVE

Copyright © 2025 MyJoVE Corporation. Todos los derechos reservados