An advanced undergraduate experiment involving the synthesis and characterization of a series of six unique cinnamamides is described. This experiment allows for a progressive mastery of skills students need to tackle more complex NMR structure elucidation problems. Characterization of the products involves IR spectroscopy, GCMS, and proton, carbon, and nitrogen NMR analyses. Understanding the principles of advanced NMR techniques, including nitrogen NMR spectroscopy, is highly relevant to advanced organic chemistry students.