Iniciar sesión

The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.

Figure1

Suppose the carboxylic acid bears an electron-withdrawing substituent. In that case, it stabilizes the conjugate base through the electron-withdrawing inductive effect, thereby decreasing the electron density on the carboxylate anion and enhancing the carboxylic acid's acidity. The presence of an electron-donating substituent destabilizes the conjugate carboxylate anion via the electron-donating inductive effect and, thus, decreases the acidity of the carboxylic acid.

The acidity of carboxylic acids also depends on the electronegativity of the substituent, the number of substituents bonded, and the proximity of the substituent from the –COOH group. Thus, fluoroacetic acid is more acidic than chloroacetic acid, as fluorine is more electronegative than chlorine. Trichloroacetic acid is more acidic than di- and monochloro acetic acid.

Tags
Substituent EffectsAcidityCarboxylic AcidsConjugate BaseCarboxylate AnionElectron withdrawing SubstituentElectron donating SubstituentInductive EffectElectronegativityFluoroacetic AcidChloroacetic AcidTrichloroacetic Acid

Del capítulo 13:

article

Now Playing

13.4 : Substituent Effects on Acidity of Carboxylic Acids

Carboxylic Acids

6.2K Vistas

article

13.1 : Nomenclatura IUPAC de ácidos carboxílicos

Carboxylic Acids

8.1K 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

6.3K Vistas

article

13.5 : Espectroscopía IR y UV-Vis de ácidos carboxílicos

Carboxylic Acids

3.5K 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

17.5K Vistas

article

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

Carboxylic Acids

7.4K 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

6.0K Vistas

article

13.15 : Ácidos carboxílicos a alcoholes primarios: reducción de hidruros

Carboxylic Acids

2.4K Vistas

See More

JoVE Logo

Privacidad

Condiciones de uso

Políticas

Investigación

Educación

ACERCA DE JoVE

Copyright © 2025 MyJoVE Corporation. Todos los derechos reservados