The synthesis of N-benzyl-2-azanorbornene via aqueous hetero Diels–Alder reaction of cyclopentadiene and benzyliminium chloride formed in situ from benzylamine hydrochloride and formaldehyde is described. Characterization of the product was achieved by IR and NMR spectroscopies. The spectral data acquired are thoroughly discussed. Numerous coupling constants were extracted from the 1H NMR spectrum. They provide a valuable material to familiarize students with the different types of proton–proton coupling patterns and their typical ranges. Karplus type correlations served to calculate 3J vicinal coupling constants as a function of dihedral angles. These computational studies involved molecular modeling. Because the synthetic part is rather straightforward and easy to carry out, this experiment is suitable for an introductory laboratory course where it can serve to illustrate the concepts of green chemistry and atom efficiency. Emphasis can also be placed on structural analysis for use within a spectroscopy course even if there is no activity component associated with it. Last but not least, the whole project provides ample materials for an advanced undergraduate laboratory in green chemistry that combines organic synthesis, structural analysis, and theoretical calculations.
Supplement
A handout for the students; answers to questions and notes for the instructor; analytical data and detailed structural analysis of N-benzyl-2-azanorbornene together with its full IR, 1H, 13C, COSY, and HETCOR NMR spectra; and CAS registry numbers for all chemicals; A poster and a slideshow presenting the main features of this project are also available as Apple Keynote, Microsoft PowerPoint, or pdf files.
Experiments, laboratory exercises, lecture demonstrations, and other descriptions of the use of chemicals, apparatus, instruments, computers, and computer interfaces are presented in the Journal of Chemical Education as illustrative of new or improved ideas or concepts in chemistry instruction and are directed at qualified teachers. Although every effort is made to assure and encourage safe practices and safe use of chemicals, the Journal of Chemical Education cannot assume responsibility for uses made of its published materials. Many chemicals are hazardous. Precautions for the safe use of hazardous chemicals and directions for their proper disposal are described in the Material Safety Data Sheets and on the labels. We strongly urge all those planning to use materials from our pages to make choices and to develop procedures for laboratory and classroom safety in accordance with local needs and situations.
Our Secondary School editors work hard to distill all the JCE materials to produce a fraction of particular interest to high school teachers. We call it CLIC.
In recent years we have worked hard to better match our advertisers with our readers. When shopping for chemistry education materials, visit our advertisers' WWW sites first.
Take JCE along on your outreach missions. Copies of the Journal, guest access to JCE Online, our publications catalog, and more are available for your participants.
Caution! 
