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ERIC Number: EJ925957
Record Type: Journal
Publication Date: 2011-Mar
Pages: 3
Abstractor: As Provided
Reference Count: 13
ISSN: ISSN-0021-9584
Chemoselective Reactions of Citral: Green Syntheses of Natural Perfumes for the Undergraduate Organic Laboratory
Cunningham, Anna D.; Ham, Eun Y.; Vosburg, David A.
Journal of Chemical Education, v88 n3 p322-324 Mar 2011
Chemoselectivity is a central concept in organic synthesis and may be readily appreciated in the context of the fragrant, polyfunctional natural product citral. We describe three single-step reactions students may perform on citral to synthesize other natural perfumes: citronellal, geraniol, nerol, or epoxycitral. Each of the reactions uses a simple catalyst and results in a crude product that may be analyzed directly. Hazards and waste are kept to a minimum. Product characterization may include thin-layer chromatography, NMR and IR spectroscopy, GC-MS, and smell. These reactions are chemoselective, biomimetic, and illustrate several principles of green chemistry. (Contains 3 schemes and 2 notes.)
Division of Chemical Education, Inc and ACS Publications Division of the American Chemical Society. 1155 Sixteenth Street NW, Washington, DC 20036. Tel: 800-227-5558; Tel: 202-872-4600; 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