A Wet-Lab Approach to Stereochemistry Using [superscript 31]P NMR Spectroscopy

Understanding stereochemistry is an important and difficult task for students to master in organic chemistry. In both introductory and advanced courses, students are encouraged to explore the spatial relationships between molecules, but this exploration is often limited either to the lecture hall or the confines of the library. As such, we sought to develop an experiment-based approach that would facilitate investigation of stereochemical principles in an organic chemistry laboratory. Herein is reported a [superscript 31]P NMR-based experiment that allows students to explore the different stereochemical outcomes when enantiopure or racemic alcohols are coupled to an achiral phosphorous center. (Contains 1 figure and 2 schemes.)