An experimental protocol that provides an excellent way to discuss concepts at the crossroads of organic chemistry and biochemistry employing biocatalysis is presented. By evaluating several reaction parameters (enzyme source, organic solvent, and acyl donor), it was possible to conduct an enzymatic kinetic resolution experiment using 1-phenylethanol as a model compound. Students were then challenged to revisit and explore a variety of basic principles already addressed in previous organic chemistry or biochemistry courses to stimulate interdisciplinary research.