An investigative case study involving the preparation of a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver esterase and orange peel esterase is described. Students work collaboratively to prepare and characterize the library of esters and complete and evaluate the feasibility of the enzymatic hydrolysis for the goals of the case. Students make extensive use of [superscript 1]H NMR to characterize products and to determine the product or products of the enzymatic reaction. The interdisciplinary nature of this experiment in the context of a case study allows students to make connections to biology; see how chemical and biological approaches to a problem differ and complement each other; gain experience in a sequential three-step synthesis and the characterization of mixtures; and develop group skills and reflective judgment. (Contains 1 schema.)