Chapter 14
Carboxylic Acid Derivatives
![Carboxylic Acid Derivatives: Overview](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12354.jpg)
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common…
![Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12355.jpg)
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid”…
![Structures of Carboxylic Acid Derivatives](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12356.jpg)
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or…
![Physical Properties of Carboxylic Acid Derivatives](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12826.jpg)
Intermolecular forces dictate several physical properties such as boiling points, melting points, solubilities, and so forth. They are classified…
![Spectroscopy of Carboxylic Acid Derivatives](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12358.jpg)
Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl…
![Relative Reactivity of Carboxylic Acid Derivatives](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12359.jpg)
Carboxylic acid derivatives such as acid halides, anhydrides, esters, and amides undergo nucleophilic acyl substitution reactions with varying…
![Acid Halides to Carboxylic Acids: Hydrolysis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12361.jpg)
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction…
![Acid Halides to Esters: Alcoholysis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12362.jpg)
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce…
![Acid Halides to Alcohols: LiAlH<sub>4</sub> Reduction](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12364.jpg)
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps.…
![Acid Halides to Alcohols: Grignard Reaction](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12827.jpg)
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the…
![Preparation of Acid Anhydrides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12366.jpg)
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of…
![Reactions of Acid Anhydrides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12367.jpg)
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ…
![Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12369.jpg)
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction…
![Esters to Alcohols: Hydride Reductions](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12370.jpg)
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents…
![Preparation of Amides](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12371.jpg)
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The…
![Amides to Carboxylic Acids: Hydrolysis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12372.jpg)
Amides can undergo either acid-catalyzed hydrolysis or base-promoted hydrolysis through a typical nucleophilic acyl substitution. Each hydrolysis…
![Preparation of Nitriles](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12374.jpg)
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide…
![Nitriles to Carboxylic Acids: Hydrolysis](https://cloudfront.jove.com/files/media/science-education/science-education-thumbs/12375.jpg)
Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide…
![Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile](https://cloudfront.jove.com/files/thumbs/58803_t.png)
The Steglich esterification is a widely-used reaction for the synthesis of esters from carboxylic acids and alcohols. While efficient and mild, the…
![Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts](https://cloudfront.jove.com/files/thumbs/52401_t.png)
Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
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Ynones are a valuable functional group and building block in organic synthesis. Ynones serve as a precursor to many important organic functional…