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  Home > JCE Print > Journal of Chemical Education > Issues > 2001  > September  >
In the Laboratory
Looking beyond the endo Rule in a Diels-Alder Discovery Lab
Ronald M. Jarret, Jamie New, Rebecca Hurley, and Laura Gillooly
Chemistry Department, College of the Holy Cross, Worcester, MA 01610-2395
Cover
September 2001
Vol. 78 No. 9
p. 1262
Abstract
The commonly described reaction of maleic anhydride and cyclopentadiene generates a Diels-Alder product in accord with the endo rule. Replacing the dienophile with maleic acid or fumaric acid (with modified reaction conditions) allows students to discover or verify that the Diels-Alder reaction is stereospecific with respect to the stereochemistry of the alkene. The recording of NMR spectra is a particularly useful means of establishing cis-trans stereochemistry (symmetry) of the products.
Supplement
Instructor's notes, detail for the procedure and interpretation of the spectra, and some sample spectra are available.
*  Contents JCE2001p1262W.doc (MS Word)
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*  Citation
 Jarret, Ronald M.; New, Jamie; Hurley, Rebecca; Gillooly, Laura. J. Chem. Educ. 2001 78 1262.
*  Keywords
 Inquiry-Based / Discovery Method; Laboratory Instruction; NMR Spectrometry; Organic Synthesis; Pericyclic Reactions; Stereochemistry
*  History
 Created:
Last Updated:		 August 14, 2001
August 31, 2005
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