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ERIC Number: EJ824929
Record Type: Journal
Publication Date: 2008-Jan
Pages: 3
Abstractor: As Provided
Reference Count: 17
ISSN: ISSN-0021-9584
Extensions of a Basic Laboratory Experiment: [4+2] and [2+2] Cycloadditions
Amarne, Hazem Y.; Bain, Alex D.; Neumann, Karen; Zelisko, Paul M.
Journal of Chemical Education, v85 n1 p104-106 Jan 2008
We describe an extended third-year undergraduate chemistry laboratory exercise in which a number of techniques and concepts are applied to the same set of chemical reactions. The reactions are the photochemical and thermal cycloadditions of [beta]-nitrostyrene and 2,3-dimethylbutadiene. This can be viewed as a single long lab or a series of connected exercises exploring a number of themes. This serves as an example of the goals and pedagogy used in a course designed to prepare students for a fourth-year undergraduate thesis. The exercises include synthesis, NMR spectroscopy, and computer-based molecular modeling. The same reagents are used, but the photochemical reaction gives the [2+2] product and the thermal reaction produces the [4+2] product. These reactions are used as a basis for discussions of a number of topics: the Woodward-Hoffmann rules, stereochemistry and regiochemistry, kinetic versus thermodynamic control of reactions, analysis of stereochemistry by 1D NMR, introduction of 2D NMR methods, molecular modeling, and use of computer programs for accurate visualization. This set of exercises is an example of an extension of the typical three-hour lab into more detailed investigations and an introduction to research methods.
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A