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Chapter 14

Carboxylic Acid Derivatives

Dérivés de l’acide carboxylique : aperçu
Dérivés de l’acide carboxylique : aperçu
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic ...
Nomenclature des dérivés de l’acide carboxylique : halogénures acides, esters et anhydrides acides
Nomenclature des dérivés de l’acide carboxylique : halogénures acides, esters et anhydrides acides
Naming Acid Halides The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to ...
Nomenclature des dérivés de l’acide carboxylique : amides et nitriles
Nomenclature des dérivés de l’acide carboxylique : amides et nitriles
Naming Amides The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and ...
Structures des dérivés de l’acide carboxylique
Structures des dérivés de l’acide carboxylique
Structure of Carboxylic Acid Derivatives Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or ...
Propriétés physiques des dérivés de l’acide carboxylique
Propriétés physiques des dérivés de l’acide carboxylique
Intermolecular forces dictate several physical properties such as boiling points, melting points, solubilities, and so forth. They are classified into ...
Acidité et basicité des dérivés de l’acide carboxylique
Acidité et basicité des dérivés de l’acide carboxylique
Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In ...
Spectroscopie des dérivés de l’acide carboxylique
Spectroscopie des dérivés de l’acide carboxylique
Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond ...
Réactivité relative des dérivés de l’acide carboxylique
Réactivité relative des dérivés de l’acide carboxylique
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying degrees of ...
Substitution d’acyle nucléophile de dérivés d’acide carboxylique
Substitution d’acyle nucléophile de dérivés d’acide carboxylique
Nucleophilic acyl substitution is an important class of substitution reactions involving a nucleophile and an acyl compound, such as carboxylic acids and ...
Halogénures acides en acides carboxyliques : hydrolyse
Halogénures acides en acides carboxyliques : hydrolyse
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction ...
Halogénures acides en esters : alcoolyse
Halogénures acides en esters : alcoolyse
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce ...
Halogénures acides en amides : aminolyse
Halogénures acides en amides : aminolyse
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react ...
Halogénures acides en alcools : réduction du LiAlH<sub>4</sub>
Halogénures acides en alcools : réduction du 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. ...
Halogénures acides en alcools : réaction de Grignard
Halogénures acides en alcools : réaction de Grignard
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the ...
Halogénures acides en cétones : réactif Gilman
Halogénures acides en cétones : réactif Gilman
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at ...
Préparation des anhydrides acides
Préparation des anhydrides acides
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic ...
Réactions des anhydrides acides
Réactions des anhydrides acides
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in ...
Esters en acides carboxyliques : saponification
Esters en acides carboxyliques : saponification
Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution ...
Esters en acides carboxyliques : hydrolyse catalysée par l’acide
Esters en acides carboxyliques : hydrolyse catalysée par l’acide
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in ...
Esters en alcools : réduction de l’hydrure
Esters en alcools : réduction de l’hydrure
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of ...
Des esters aux alcools : la réaction de Grignard
Des esters aux alcools : la réaction 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 ...
Préparation des amides
Préparation des amides
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC). The ...
Amides aux acides carboxyliques : hydrolyse
Amides aux acides carboxyliques : hydrolyse
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis requires ...
Amides à amines : réduction de LiAlH<sub>4</sub>
Amides à amines : réduction de LiAlH4
Amide reduction with strong reducing agents like lithium aluminum hydride proceeds through a nucleophilic acyl substitution to form amines. Primary, ...
Préparation des nitriles
Préparation des nitriles
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or ...
Nitriles en acides carboxyliques : hydrolyse
Nitriles en acides carboxyliques : hydrolyse
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate. The ...
Nitriles en cétones : réaction de Grignard
Nitriles en cétones : réaction de Grignard
Organomagnesium halides, commonly known as Grignard reagents, convert nitriles to ketones and proceed through a nucleophilic acyl substitution. Nitriles ...
Nitriles en amines : réduction de LiAlH<sub>4</sub>
Nitriles en amines : réduction 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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