Spectroscopic Properties of Some Simple Esters. A Practical Application of Synthesis and Spectroscopy in the Undergraduate Organic Laboratory

Abstract

This exercise, the synthesis and spectroscopic analysis of the allyl esters of some aromatic carboxylic acids, consists of a series of open-ended experiments. It was designed for the honors organic chemistry student, but can be easily adapted to fit the regular second-semester organic chemistry program. The primary objective of this exercise is to prepare students for research in organic synthesis. Thus, a series of synthetic transformations are described, incorporating the basic techniques of isolation, TLC and flash chromatographic purification, IR and NMR analyses, as well as the method of synthesis involving phase transfer catalysis. These experiments allow the students to monitor the effect of hydrogen bonding on the IR stretching frequencies for the hydroxyl and carbonyl groups, as well as to provide them with an excellent opportunity to examine the phenomenon of proton spin-coupling in the NMR spectra of simple organic systems.