Iniciar sesión

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.

In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride ion. In the last step, the amide nitrogen is deprotonated by another equivalent of the amine to give the final substitution product.

Figure1

If the amine is expensive, the reaction is performed with one equivalent of the amine and a second equivalent of an inexpensive base like triethylamine, pyridine, or sodium hydroxide.

Tags
Acid HalidesAminolysisNucleophilic Acyl SubstitutionAmmoniaAminesPrimary AmidesSecondary AmidesTertiary AmidesTetrahedral IntermediateChloride IonDeprotonationTriethylaminePyridineSodium Hydroxide

Del capítulo 14:

article

Now Playing

14.12 : Acid Halides to Amides: Aminolysis

Carboxylic Acid Derivatives

2.5K Vistas

article

14.1 : Derivados del ácido carboxílico: descripción general

Carboxylic Acid Derivatives

3.1K Vistas

article

14.2 : Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos

Carboxylic Acid Derivatives

3.8K Vistas

article

14.3 : Nomenclatura de los derivados del ácido carboxílico: amidas y nitrilos

Carboxylic Acid Derivatives

3.6K Vistas

article

14.4 : Estructuras de los derivados del ácido carboxílico

Carboxylic Acid Derivatives

2.3K Vistas

article

14.5 : Propiedades físicas de los derivados del ácido carboxílico

Carboxylic Acid Derivatives

2.4K Vistas

article

14.6 : Acidez y basicidad de los derivados del ácido carboxílico

Carboxylic Acid Derivatives

3.3K Vistas

article

14.7 : Espectroscopía de derivados del ácido carboxílico

Carboxylic Acid Derivatives

2.2K Vistas

article

14.8 : Reactividad relativa de los derivados del ácido carboxílico

Carboxylic Acid Derivatives

2.4K Vistas

article

14.9 : Sustitución nucleofílica de acilo de derivados del ácido carboxílico

Carboxylic Acid Derivatives

2.7K Vistas

article

14.10 : Halogenuros ácidos a ácidos carboxílicos: hidrólisis

Carboxylic Acid Derivatives

2.4K Vistas

article

14.11 : Halogenuros ácidos a ésteres: alcoholisis

Carboxylic Acid Derivatives

2.6K Vistas

article

14.13 : Halogenuros ácidos a alcoholes: reducción de LiAlH4

Carboxylic Acid Derivatives

2.6K Vistas

article

14.14 : Halogenuros ácidos a alcoholes: reacción de Grignard

Carboxylic Acid Derivatives

2.0K Vistas

article

14.15 : Halogenuros ácidos a cetonas: reactivo de Gilman

Carboxylic Acid Derivatives

2.6K Vistas

See More

JoVE Logo

Privacidad

Condiciones de uso

Políticas

Investigación

Educación

ACERCA DE JoVE

Copyright © 2025 MyJoVE Corporation. Todos los derechos reservados