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ERIC Number: EJ913063
Record Type: Journal
Publication Date: 2010-Jan
Pages: 3
Abstractor: As Provided
Reference Count: 13
ISBN: N/A
ISSN: ISSN-0021-9584
Microwave-Enhanced Organic Syntheses for the Undergraduate Laboratory: Diels-Alder Cycloaddition, Wittig Reaction, and Williamson Ether Synthesis
Baar, Marsha R.; Falcone, Danielle; Gordon, Christopher
Journal of Chemical Education, v87 n1 p84-86 Jan 2010
Microwave heating enhanced the rate of three reactions typically performed in our undergraduate organic chemistry laboratory: a Diels-Alder cycloaddition, a Wittig salt formation, and a Williamson ether synthesis. Ninety-minute refluxes were shortened to 10 min using a laboratory-grade microwave oven. In addition, yields improved for the Wittig salt and ether preparations. The Diels-Alder cycloaddition of "N"-phenylmaleimide and 1,3-cyclohexadiene in absolute ethanol in a closed vessel and 130 [degree]C gave 84-90% yields. Formation of the Wittig salt, benzyltriphenylphosphonium chloride, from triphenylphosphine and benzyl chloride gave yields greater than 90% when heated in acetonitrile at 200 [degree]C Yields doubled in the Williamson ether synthesis of 2-ethoxynaphthalene, from 2-naphthol, methanolic potassium hydroxide, and iodoethane with microwave heating at 130 [degree]C. (Contains 1 table and 7 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: eic@jce.acs.org; Web site: http://pubs.acs.org/jchemeduc
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A