ERIC Number: EJ814862
Record Type: Journal
Publication Date: 2008-Nov
Pages: 2
Abstractor: As Provided
ISBN: N/A
ISSN: ISSN-0021-9584
EISSN: N/A
The Synthesis of a Cockroach Pheromone: An Experiment for the Second-Year Organic Chemistry Laboratory
Feist, Patty L.
Journal of Chemical Education, v85 n11 p1548-1549 Nov 2008
This experiment describes the synthesis of gentisyl quinone isovalerate, or blattellaquinone, a sex pheromone of the German cockroach that was isolated and identified in 2005. The synthesis is appropriate for the second semester of a second-year organic chemistry laboratory course. It can be completed in two, three-hour laboratory periods and uses equipment readily available in most organic chemistry laboratories. In the first step, 2,5-dimethoxybenzyl alcohol reacts with isovaleryl chloride to produce 2,5-dimethoxybenzyl 3-methylbutanoate. In the second step, the 2,5-dimethoxybenzyl 3-methylbutanoate is oxidized using ceric ammonium nitrate to form gentisyl quinone isovalerate. The experiment is interesting to students because it involves the synthesis of a compound that has real-world applications. The experiment affords them practice in the important techniques of extraction, IR spectroscopy, and NMR spectroscopy. (Contains 1 figure.)
Descriptors: Spectroscopy, Organic Chemistry, Science Experiments, Science Laboratories, College Science, Entomology, Science Instruction, Science Process Skills
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: jchemed@egpp.com; Web site: http://www.jce.divched.org
Publication Type: Journal Articles; Reports - Evaluative
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A