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Related Concept Videos

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.0K
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...
3.0K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

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

8.0K
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.
8.0K
Acid Halides to Esters: Alcoholysis01:12

Acid Halides to Esters: Alcoholysis

2.9K
Alcoholysis is a nucleophilic acyl substitution reaction in which an alcohol functions as a nucleophile. Acid halides react with alcohol to produce esters. The mechanism proceeds in three steps:
2.9K
Esters to β-Ketoesters: Claisen Condensation Mechanism01:08

Esters to β-Ketoesters: Claisen Condensation Mechanism

3.7K
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...
3.7K
Esters to Carboxylic Acids: Saponification01:25

Esters to Carboxylic Acids: Saponification

4.5K
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...
4.5K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview01:20

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

18.2K
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.
18.2K

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Updated: Jul 17, 2025

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

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Reaction Pathways in Carbonates and Esters.

Pietro Tundo1,2, Fabio Aricò3

  • 1Ca' Foscari University of Venice, Campus Scientifico, via Torino 155, 30172, Venezia Mestre, Italy.

Chemsuschem
|September 1, 2023
PubMed
Summary
This summary is machine-generated.

This review explores the intricate reaction mechanisms of carbonates, comparing their reactivity to esters. It proposes a theoretical model for understanding these intertwined processes, highlighting greener synthesis pathways.

Keywords:
CO2 ChemistryDialkyl carbonatesEstersGreen ChemistryReaction mechanisms

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Area of Science:

  • Organic Chemistry
  • Physical Chemistry
  • Green Chemistry

Background:

  • Carbonates and esters exhibit complex reactivity influenced by various catalytic mechanisms.
  • Understanding the interplay between acyl and alkyl cleavage is crucial for predicting reaction outcomes.
  • Existing literature provides experimental data on these reactions, necessitating a unifying theoretical framework.

Purpose of the Study:

  • To analyze and compare the reactivity of carbonates and esters.
  • To propose a theoretical model for the intertwined base- and acid-catalyzed mechanisms (BAc2/BAl2, AAc2/AAl2, AAl1).
  • To investigate the role of entropic and anchimeric effects in carbonate reactions.

Main Methods:

  • Comprehensive review and analysis of existing experimental data from scientific literature.
  • Development of a theoretical model to explain energy profiles of competing reaction mechanisms.
  • Comparative analysis of carbonate and ester reactivity under various catalytic conditions.

Main Results:

  • A theoretical model was proposed, outlining energy profile differences for BAc2/BAl2 and AAc2/AAl2/AAl1 mechanisms.
  • Carbonate reactions are driven by precise sequences of BAc2-BAl2 or AAl2-AAc2 mechanisms.
  • Entropic and anchimeric effects reduce Gibbs activation energy, enabling transformations at lower temperatures and requiring only catalytic base amounts.

Conclusions:

  • Carbonate chemistry involves tightly interconnected reaction pathways crucial for product formation.
  • Specific effects like cyclization and anchimeric assistance significantly lower activation energy barriers.
  • Carbonates offer greener synthesis alternatives compared to chlorine chemistry, reducing environmental impact.