|
|
| Home > JCE Print > Journal of Chemical Education > Issues >
1997
>
December
> |
|
In the Laboratory
|
|
|
|
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course
|
Keith F. McDaniel and R. Matthew Weekly
Ohio University, Department of Chemistry, Clippinger Laboratories, Athens, OH 45701-2979
|
|
December 1997
Vol. 74 No. 12
p. 1465
|
|
|
|
| Abstract |
|
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session. The resulting product, which contains four new stereocenters, crystallizes upon cooling of the reaction mixture to give the pure product. Careful analysis of the 1H nuclear magnetic resonance spectrum, which contains a variety of cleanly split signals with no overlapping peaks, allows for assignment of all twelve hydrogens. A COSY spectrum of the product is also presented and interpreted.
|
|
| More Information |
 Citation |
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997 74 1465.
|
Keywords |
Organic Chemistry, Laboratory Instruction, Organic Synthesis, Pericyclic Reactions, and NMR Spectrometry
|
History |
Created:
Last Updated: |
July 20, 1999
June 23, 2005
|
|
|
|
|
|
| Home > JCE Print > Journal of Chemical Education > Issues >
1997
>
December
> Page
1465
|
|
|
| JCE HS CLIC |
|
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.
|
| Contributions Welcome |
| JCE welcomes your submission |
| Advertisers |
| 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. |
| Be An Ambassador |
| 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. |
|
