Using advanced spectroscopic techniques to provide a fresh look at the Diels-Alder reaction in undergraduate organic chemistry

CHED 107

Timm A. Knoerzer, tknoerz7@naz.edu, Department of Chemistry, Nazareth College of Rochester, 4245 East Avenue, Rochester, NY 14618 and Norman Heimer, norm.heimer@usafa.af.mil, Department of Chemistry, U.S. Air Force Academy, 2355 Fairchild Drive Suite 2N 225, HQ USAFA/DFC, USAF Academy, CO 80840.
The Diels-Alder reaction is a standard reaction taught in undergraduate organic chemistry courses and laboratories. One of the best examples involves the reaction of alpha-phellandrene with maleic anhydride in refluxing ether to produce a wonderful white crystalline product. However, standard analyses of this reaction product rarely proceed past the level of melting point determination. An excellent opportunity exists here for students to explore in depth the three-dimensional structure of this Diels-Alder adduct. Herein, we report the utilization of several spectroscopic strategies that students can employ to elucidate the structure of the adduct. In particular, several NMR techniques can be used to assign proton and carbon signals and X-ray analysis can be utilized to assign the stereochemistry to the single chiral center in the product molecule.
 

General Posters
7:30 PM-9:30 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Sci-Mix

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008