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Chapter 14

Carboxylic Acid Derivatives

Derivados del ácido carboxílico: descripción general
Derivados del ácido carboxílico: descripción general
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic ...
Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos
Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos
Naming Acid Halides The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to ...
Nomenclatura de los derivados del ácido carboxílico: amidas y nitrilos
Nomenclatura de los derivados del ácido carboxílico: amidas y nitrilos
Naming Amides The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and ...
Estructuras de los derivados del ácido carboxílico
Estructuras de los derivados del ácido carboxílico
Structure of Carboxylic Acid Derivatives Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or ...
Propiedades físicas de los derivados del ácido carboxílico
Propiedades físicas de los derivados del ácido carboxílico
Intermolecular forces dictate several physical properties such as boiling points, melting points, solubilities, and so forth. They are classified into ...
Acidez y basicidad de los derivados del ácido carboxílico
Acidez y basicidad de los derivados del ácido carboxílico
Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In ...
Espectroscopía de derivados del ácido carboxílico
Espectroscopía de derivados del ácido carboxílico
Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond ...
Reactividad relativa de los derivados del ácido carboxílico
Reactividad relativa de los derivados del ácido carboxílico
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of ...
Sustitución nucleofílica de acilo de derivados del ácido carboxílico
Sustitución nucleofílica de acilo de derivados del ácido carboxílico
Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and ...
Halogenuros ácidos a ácidos carboxílicos: hidrólisis
Halogenuros ácidos a ácidos carboxílicos: hidrólisis
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction ...
Halogenuros ácidos a ésteres: alcoholisis
Halogenuros ácidos a ésteres: alcoholisis
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce ...
Halogenuros ácidos a amidas: aminolis
Halogenuros ácidos a amidas: aminolis
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react ...
Halogenuros ácidos a alcoholes: reducción de LiAlH<sub>4</sub>
Halogenuros ácidos a alcoholes: reducción de LiAlH4
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride. The mechanism proceeds in three steps. ...
Halogenuros ácidos a alcoholes: reacción de Grignard
Halogenuros ácidos a alcoholes: reacción de Grignard
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the ...
Halogenuros ácidos a cetonas: reactivo de Gilman
Halogenuros ácidos a cetonas: reactivo de Gilman
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at ...
Preparación de anhídridos ácidos
Preparación de anhídridos ácidos
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic ...
Reacciones de los anhídridos ácidos
Reacciones de los anhídridos ácidos
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in ...
Ésteres a ácidos carboxílicos: saponificación
Ésteres a ácidos carboxílicos: saponificación
Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution ...
Ésteres a ácidos carboxílicos: hidrólisis catalizada por ácido
Ésteres a ácidos carboxílicos: hidrólisis catalizada por ácido
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in ...
Ésteres a alcoholes: reducciones de hidruros
Ésteres a alcoholes: reducciones de hidruros
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of ...
Ésteres a alcoholes: reacción de Grignard
Ésteres a alcoholes: reacción de Grignard
The reaction of an ester with a Grignard reagent, followed by hydrolysis of the magnesium alkoxide salt in aqueous acid, yields a tertiary alcohol. In the ...
Preparación de amidas
Preparación de amidas
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC). The ...
Amidas a los ácidos carboxílicos: hidrólisis
Amidas a los ácidos carboxílicos: hidrólisis
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires ...
Amidas a Aminas: Reducción de LiAlH<sub>4</sub>
Amidas a Aminas: Reducción de LiAlH4
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, ...
Preparación de nitrilos
Preparación de nitrilos
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or ...
Nitrilos a ácidos carboxílicos: hidrólisis
Nitrilos a ácidos carboxílicos: hidrólisis
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate. The ...
De nitrilos a cetonas: reacción de Grignard
De nitrilos a cetonas: reacción de Grignard
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles ...
De nitrilos a aminas: reducción de LiAlH<sub>4</sub>
De nitrilos a aminas: reducción de LiAlH4
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. ...
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