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The Synthesis of a Cockroach Pheromone. An Experiment for the Second-Year Organic Chemistry Laboratory

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Patty L. Feist

Department of Chemistry and Biochemistry, University of Colorado, Boulder, CO 80309

J. Chem. Educ., 2008, 85 (11), p 1548

DOI: 10.1021/ed085p1548

Publication Date (Web): November 1, 2008

Section:

History, Education, and Documentation

Abstract

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Esters

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

Molecular Models of Natural Products
William F. Coleman
Journal of Chemical Education2008 85 (11), 1584
- Molecular Models of Natural Products
  William F. Coleman
  Journal of Chemical Education2008 85 (11), 1584
  This month’s Featured Molecules focus on natural products and include blattellquinone, a sex pheromone secreted by female German cockroaches to attract males, and (R)-limonene, a secondary metabolite found in citrus fruit peels.
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