ACID-CATALYZED HYDROLYSIS OF 2-METHOXYPROPENAL

Article abstract of DOI:10.1016/0008-6215(83)88137-3

2-Methoxypropenal in acid media undergoes general acid-catalyzed hydrolysis with formation of 2-oxopropanal.The kinetics of this reaction were studied, the rate constants established, and a reaction mechanism is suggested.Hydrolysis of 2-methoxypropenal is governed by a mechanism of the vinyl ether type, and the presence of the aldehyde group causes a decrease in the reaction rate.The analogy of the acid-catalyzed hydrolysis of 2-methoxypropenal to that of a vinyl ether was shown by the solvent isotope-effect, k_D/k_H=0.41, and the value of the Broensted exponent, α=0.60.The activation parameters found and quantum-chemical calculations of charge distribution in 2-methoxypropenal and other model compounds were also utilized to explain the mechanism of the acid-catalyzed hydrolysis of the title compound.