Investigation of 1H NMR Chemical Shift in Various Systems

A set of five advanced undergraduate experiments teaching specialized 1D 1H NMR topics is presented. The organization of these laboratory projects is such that students carry out one experiment then teach the concepts covered to the rest of the class through brief oral presentations of their data. Student learning is assessed through a written report where students must analyze and explain all five experiments. With this arrangement, five distinct topics in 1H NMR are covered in depth in one or two laboratory meetings, compared to five separate sessions. The projects contained here illustrate the interpretation of spectra from compounds with exchangeable protons, intramolecular hydrogen bonding, keto-enol tautomers and the use of lanthanide shift reagents. References to supplemental experiments are included so instructors can select the experiments and depth of analysis based on laboratory time, NMR instrumentation, student background and class size.