The Fisher esterification reaction is ideally suited for the undergraduate organic laboratory because it is easy to carry out and often involves a suitable introduction to basic laboratory techniques including extraction, distillation, and simple spectroscopic (IR and NMR) analyses. Here, a Fisher esterification reaction is described in which the product is also ideally suited for more in-depth analyses of NMR assignments using standard 2D NMR techniques as well as incorporating molecular modeling arguments and the Karplus relationship between torsional angles and vicinal coupling constants to assign [superscript 1]H NMR signals to specific diastereotopic hydrogens. (Contains 2 figures.)