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Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

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...

Catalysis

Catalysis

Catalysis influences the rate of chemical reactions by providing an alternative reaction pathway with lower activation energy. A catalyst speeds up a reaction, but it is not consumed during the process. The fundamental principle of catalysis is the ability of a catalyst to alter the reaction mechanism, often introducing a more efficient pathway than the uncatalyzed process.In a catalyzed reaction, the catalyst participates directly in the reaction mechanism. It interacts with reactants to form...

Catalysis

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

Acid Halides to Carboxylic Acids: Hydrolysis

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.

Acid-Catalyzed Hydration of Alkenes

Acid-Catalyzed Hydration of Alkenes

Alkenes react with water in the presence of an acid to form an alcohol. In the absence of acid, hydration of alkenes does not occur at a significant rate, and the acid is not consumed in the reaction. Therefore, alkene hydration is an acid-catalyzed reaction.

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Related Experiment Video

Updated: Jul 15, 2026

Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins

Expression, Purification, Crystallization, and Enzyme Assays of Fumarylacetoacetate Hydrolase Domain-Containing Proteins

Published on: June 20, 2019

Acid catalysis in basic solution: a supramolecular host promotes orthoformate hydrolysis.

Michael D Pluth¹, Robert G Bergman, Kenneth N Raymond

¹Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720, USA.

Science (New York, N.Y.)

|April 7, 2007

Summary

Synthetic catalysts can now accelerate chemical reactions in basic solutions. A novel metal-ligand assembly stabilizes protonated substrates, enabling efficient orthoformate hydrolysis with significant rate enhancements.

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Last Updated: Jul 15, 2026

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Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

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Published on: August 23, 2018

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks (MOFs)

Published on: January 17, 2020

Area of Science:

Supramolecular Chemistry
Catalysis
Organic Synthesis

Background:

Enzymes utilize electrostatic environments for substrate tuning, a challenging strategy for synthetic systems.
Mimicking enzyme active sites in artificial host-guest complexes remains an area of active research.

Purpose of the Study:

To design and synthesize a novel metal-ligand assembly capable of catalyzing reactions in basic media.
To investigate the stabilization of protonated substrates within a hydrophobic cavity.
To achieve significant rate accelerations for orthoformate hydrolysis using a synthetic catalyst.

Main Methods:

Construction of a highly charged, water-soluble metal-ligand assembly with a hydrophobic interior.
Kinetic studies to determine reaction rates and mechanisms, including Michaelis-Menten kinetics and inhibition assays.
Evaluation of substrate scope and selectivity based on molecular size.

Main Results:

The metal-ligand assembly successfully catalyzed the hydrolysis of orthoformates in basic solution.
Rate accelerations of up to 890-fold were observed compared to uncatalyzed reactions.
The catalytic process demonstrated Michaelis-Menten kinetics, competitive inhibition, and size-selective substrate binding.

Conclusions:

The developed supramolecular catalyst effectively mimics enzymatic strategies by stabilizing charged intermediates.
This system provides a novel approach for performing acid-catalyzed reactions under basic conditions using synthetic hosts.
The observed kinetics and selectivity highlight the potential of rationally designed host-guest systems in catalysis.