Related Experiment Video
Updated: Jul 11, 2026

A Simple, Low-cost, and Robust System to Measure the Volume of Hydrogen Evolved by Chemical Reactions with Aqueous Solutions
Published on: August 17, 2016
The proton inventory technique in a dual mechanistic system: the spontaneous hydrolysis of ethyl formate
1Laboratory of Bio-organic Chemistry, School of Chemistry, University of Costa Rica. jmata@cariari.ucr.ac.cr
Abstract:
Ethyl formate undergoes spontaneous hydrolysis through two parallel mechanistic pathways: water catalysis and specific hydrogen-ion catalysis. The proton inventory of the water reaction at 37.0 ( degrees )C was determined from the overall conversion curves, in H(2)O/D(2)O mixtures of deuterium atom fraction n, resulting in k(1)(n)=(2.1+/-0.1)x10(-5) s(-1) (1-n+0.42 n) (1-n+0.83 n)(2), in agreement with the results of six other cases of carboxylic acid derivatives. This result contributes to the validation of the accuracy of the proton inventory technique.
Related Concept Videos
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis
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...
Regioselective Formation of Enolates
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

