Chapter 2 Hydrolysis and Formation of Esters of Organic Acids

Abstract

The hydrolysis and formation of esters have been extensively studied than any other chemical reaction. This chapter brings together in one place a representative selection of the data to set them in the perspective of an overall view of the subject and to offer the interpretation of each type of reaction that seems most acceptable in the light of current knowledge. Simple carboxylic acids and their esters are weak bases. They are completely protonated only in very strong acidic media. The chapter reviews the recent investigations of ester hydrolysis in concentrated solutions of strong mineral acids. It is now possible to study the hydrolysis reactions of esters under conditions where the substrate is completely protonated. The properties of the protonated ester, however, are more conveniently examined using more strongly acidic media, in the absence of water, where bimolecular reactions are reduced to insignificance. At sufficiently low temperatures under these conditions, the rates of exchange of the added protons are slow and the detailed structures of protonated carboxylic acids and esters can be investigated, particularly by proton nuclear magnetic resonance (NMR) techniques.