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ERIC Number: EJ1117362
Record Type: Journal
Publication Date: 2016-Oct
Pages: 6
Abstractor: As Provided
ISSN: ISSN-0021-9584
Comparing Amide-Forming Reactions Using Green Chemistry Metrics in an Undergraduate Organic Laboratory
Fennie, Michael W.; Roth, Jessica M.
Journal of Chemical Education, v93 n10 p1788-1793 Oct 2016
In this laboratory experiment, upper-division undergraduate chemistry and biochemistry majors investigate amide-bond-forming reactions from a green chemistry perspective. Using hydrocinnamic acid and benzylamine as reactants, students perform three types of amide-forming reactions: an acid chloride derivative route; a coupling reagent promoted method; and a boric acid catalyzed condensation. After isolation of the common product, students assess the reactions using the 12 Principles of Green Chemistry and several green chemistry metrics: atom economy; reaction mass efficiency; process mass intensity; and the EcoScale. In addition to assessing what route is the greenest, students also compare the metrics to discern what aspects of green chemistry each metric captures. In order to extend sustainability to economic considerations, the projected "front-end" cost of synthesizing a kilogram of the amide is calculated based on data from each reaction. The experimental work is conducted over two 3 hour laboratory periods.
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 - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A
Grant or Contract Numbers: N/A