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ERIC Number: EJ814862
Record Type: Journal
Publication Date: 2008-Nov
Pages: 2
Abstractor: As Provided
Reference Count: 17
ISSN: ISSN-0021-9584
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.)
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 - Evaluative
Education Level: Higher Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A