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Related Concept Videos

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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

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.
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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...
Esters to Alcohols: Grignard Reaction01:08

Esters to Alcohols: Grignard Reaction

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 case of formate esters, secondary alcohols are formed.
The reaction requires two equivalents of the Grignard reagent and introduces two identical alkyl groups, derived from the Grignard reagent, bonded to the hydroxyl-bearing carbon of the alcohol.
The reaction follows the typical nucleophilic acyl substitution mechanism. The Grignard...
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

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.
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

Regular Claisen condensation involves the synthesis of β-ketoesters by combining identical ester molecules bearing two α hydrogens in the presence of an alkoxide base. The reaction commences with the deprotonation of the acidic α hydrogen by the base to form a resonance stabilized ester enolate. This nucleophilic ion then attacks the carbonyl center of another ester molecule to generate a tetrahedral alkoxide intermediate. Next, the expulsion of the alkoxide group from the intermediate restores...

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Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Efficient and controllably selective preparation of esters using uronium-based coupling agents.

Jean-d'Amour K Twibanire1, T Bruce Grindley

  • 1Department of Chemistry, Dalhousie University, Halifax, NS, Canada B3H 4J3.

Organic Letters
|May 20, 2011
PubMed
Summary
This summary is machine-generated.

New methods enable efficient synthesis of carboxylic acid esters from acids and alcohols at room temperature using peptide coupling reagents like TBTU, TATU, and COMU. Selectivity is achievable in polyols by carefully choosing the base and coupling agent.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

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Last Updated: Jun 1, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
06:52

Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile

Published on: October 30, 2018

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Carboxylic acid esters are vital functional groups in organic chemistry.
  • Traditional esterification methods often require harsh conditions or specialized reagents.

Purpose of the Study:

  • To develop a mild and efficient method for synthesizing carboxylic acid esters.
  • To explore the utility of peptide coupling reagents for ester formation.

Main Methods:

  • Esterification reactions were performed using carboxylic acids and phenols or aliphatic alcohols.
  • Peptide coupling reagents (TBTU, TATU, COMU) and organic bases were employed.
  • Reactions were conducted at room temperature.

Main Results:

  • Excellent yields of carboxylic acid esters were achieved.
  • TBTU and TATU facilitated faster reactions compared to COMU, but were ineffective with tertiary alcohols.
  • Selective esterification of primary or secondary alcohols in diols and polyols was demonstrated by varying the base and coupling agent.

Conclusions:

  • Peptide coupling reagents offer a versatile and effective route for ester synthesis under mild conditions.
  • The choice of coupling agent and base allows for control over reactivity and selectivity, particularly in complex polyol systems.