Carboxylic Acids Esters

Carboxylic acids and esters are oxygen-containing organic compounds defined by their functional groups and important roles in chemical reactions and materials. Carboxylic acids contain a carbonyl group bonded to a hydroxyl group, whereas esters contain a carbonyl group bonded to an alkoxy group; esters commonly form when a carboxylic acid reacts with an alcohol in acid-catalyzed esterification, producing water as a byproduct. Their properties, including polarity, solubility, boiling point, and characteristic odors, depend on molecular structure. These compounds support applications in fragrances, flavors, solvents, pharmaceuticals, polymers, and biological molecules, while ester hydrolysis provides a key route for converting esters back into acids and alcohols.

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JoVE Core - Organic Chemistry

Esters to Carboxylic Acids: Saponification

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2025

Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats. The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols. During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

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Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group. The mechanism of this reaction was confirmed by Robert and Urey (1938) through a radioisotope labeling experiment, where esterification of a carboxylic acid was carried out using 18O-labeled alcohol. The resulting...

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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Naming Acid Halides The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid. IUPAC: Ethanoic acid Ethanoyl chloride Common: Acetic acid Acetyl chloride Cyclic acid halides are named by replacing the suffix...

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview

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2025

The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water. Hydroxy-functionalized carboxylic acids undergo intramolecular Fischer esterification to form lactones. The cyclic five- and six-membered lactones are formed spontaneously. The reaction rate of Fischer esterification is greatly dependent on steric factors. Primary alcohols react fastest...

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