|
|
| Home > JCE Print > Journal of Chemical Education > Issues >
2001
>
May
> |
|
In the Laboratory
|
|
|
|
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences
|
Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
Ecole Nationale Supérieure d'Ingénieur de Caen, Université de Caen, ISMRA, 6Bd du Maréchal Juin, F-14050 Caen, France
|
|
May 2001
Vol. 78 No. 5
p. 654
|
|
|
|
| Abstract |
|
The synthesis of substituted butenolide is reported in two 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile). The molecules were designed to have pedagogical interest for IR and NMR spectroscopy, such as the observation of the diastereotopic effect. Molecular modeling calculations and a proton-proton homonuclear decoupling experiment for one of these compounds were carried out to demonstrate the presence of a diastereotopic effect.
|
| Supplement |
Supplemental material available includes the data used to draw Figures 2 and 3, obtained by geometry optimization of each conformation of compounds 1 and 2 accordinig to AM1 method; notes for the instructor; and NMR and IR assignments.
|
 Contents |
JCE2001p0654W.doc (MS Word)
|
| Download |
|
|
| More Information |
Citation |
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001 78 654.
|
Keywords |
IR Spectroscopy; Laboratory Instruction; Molecular Modeling / Dynamics; NMR Spectrometry; Organic Synthesis; Undergraduate Research
|
History |
Created:
Last Updated: |
March 22, 2001
August 31, 2005
|
|
|
|
|
|
| Home > JCE Print > Journal of Chemical Education > Issues >
2001
>
May
> Page
654
|
|
|
| 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. |
|
