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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...

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

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.

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

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.

Polyprotic Acids

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Esters to Carboxylic Acids: Saponification

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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.
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Related Experiment Video

Updated: Jun 22, 2026

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

Published on: October 19, 2017

In vitro release of phosphoric acid ester from self-etching primer.

B Wendl¹, P Muchitsch, M Pichelmayer

¹Department of Orthodontics and Dentofacial Orthopedics, University Graz, Auenbruggerplatz 12, A-8036 Graz, Austria. dr.b.wendl@tele2.at

Journal of Dental Research

|June 5, 2009

Summary

A significant portion of self-etching primer (SEP) remains unreacted and extractable after dental resin bonding. Doubling light curing time reduces this extractable amount, but leaching remains a concern for dental materials.

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Synthesis of High Purity Nonsymmetric Dialkylphosphinic Acid Extractants

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Fabrication of Large-area Free-standing Ultrathin Polymer Films

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Published on: June 3, 2015

Area of Science:

Biomaterials
Dental Materials Science
Polymer Chemistry

Background:

Self-etching primers (SEPs) simplify dental resin bonding by eliminating rinsing steps.
Current assumptions suggest complete incorporation of SEPs into the resin matrix.
The potential for unreacted, extractable SEP components has not been thoroughly investigated.

Purpose of the Study:

To quantify the amount of unreacted phosphoric acid ester from SEPs that remains extractable after dental bracket bonding.
To assess the impact of light curing time on the extractability of SEP components.
To determine the kinetics of SEP component leaching.

Main Methods:

Dental brackets were bonded to extracted teeth using SEPs under controlled laboratory conditions.
High-performance liquid chromatography (HPLC) was employed to measure the concentration of extractable phosphoric acid ester.
Extraction kinetics were monitored over time to assess leaching rates.

Main Results:

Approximately 50% of the applied phosphoric acid ester was found to be extractable after standard light curing, indicating incomplete incorporation into the resin.
Increasing the light curing time to double the standard duration reduced the extractable proportion to 40%.
The leaching of acid ester was rapid, with most of the extraction occurring within the first hour post-curing.

Conclusions:

A substantial amount of self-etching primer remains unreacted and extractable after dental bonding procedures.
Standard light curing protocols are insufficient for complete incorporation of SEPs into the resin matrix.
The extractability of SEP components raises potential concerns regarding their release into the oral environment over time.