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ERIC Number: EJ1050709
Record Type: Journal
Publication Date: 2015-Jan
Pages: 4
Abstractor: As Provided
Reference Count: 11
ISBN: N/A
ISSN: ISSN-0021-9584
Operationally Simple Synthesis of N,N-Diethyl-3-Methylbenzamide (DEET) Using COMU as a Coupling Reagent
Withey, Jonathan M.; Bajic, Andrea
Journal of Chemical Education, v92 n1 p175-178 Jan 2015
A novel procedure is described where students use COMU [(1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate], as a nonhazardous partner, in the one-pot coupling of a carboxylic acid and amine producing N,N-diethyl-3-methylbenzamide (DEET). Fundamental principles of carbonyl reactivity are understood, with potential for expansion to new methods of amide bond formation. The reaction can be monitored visually by virtue of the color change associated with the conversion, and all byproducts are conveniently water-soluble. This modern, microscale reaction is appropriate for a second-semester introductory undergraduate organic chemistry course: it can be performed during a 3 h laboratory period and is operationally straightforward. Curricular flexibility allows for this protocol to serve as a meaningful discussion of mechanistic organic chemistry and spectroscopy.
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
Identifiers - Location: Canada (Edmonton)