How well does the undergraduate organic chemistry laboratory curriculum prepare students for academic research, or for a bench job in industry? Running experiments that are more representative of research chemistry has the potential to better equip students for working in a research laboratory, while at the same time giving them insight into a typical outcome in a research project. We describe here an experiment that we have launched in the sophomore organic chemistry lab at UC Davis that presents challenges in chromatographic separation, structural assignment by NMR, and mechanistic interpretation. Optional exercises in computational modeling of the NMR data and chromophore analysis by UV- vis/fluorescence measurements are included.