A Robust, One-Pot Method for Acquiring Kinetic Data for Hammett Plots Used To Demonstrate Transmission of Substituent Effects in Reactions of Aromatic Ethyl Esters

A one-pot method for acquiring kinetic data for the reactions of a series of substituted aromatic esters with potassium hydroxide using C-13 NMR spectroscopy is described, which provides an efficient way to obtain sufficient data to demonstrate the Hammett equation in undergraduate laboratories. The method is time-efficient and robust, and lends itself to group work. The high throughput nature of the method allows collection of sufficient data to explore the transmission of electronic effects between the aromatic moiety and the ester functionality with varying chain lengths.