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ERIC Number: EJ1202236
Record Type: Journal
Publication Date: 2019-Jan
Pages: 5
Abstractor: As Provided
ISSN: ISSN-0021-9584
Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry to Compare and Contrast Wittig and Metathesis Methodologies
Bannin, Timothy J.; Datta, Partha P.; Kiesewetter, Elizabeth T.; Kiesewetter, Matthew K.
Journal of Chemical Education, v96 n1 p143-147 Jan 2019
In this experiment, students are asked to conduct a catalytic cross-metathesis experiment and compare this reaction to the Wittig reaction within the confines of green chemistry. Students synthesize stilbene from styrene using Grubbs second-generation catalyst. Products can be minimally characterized by IR spectroscopy and melting point, but using [superscript 1]H NMR spectroscopy is preferred. Students find that the Wittig reaction is selective for "cis"-stilbene while the metathesis reaction produces >98% "trans"-stilbene. Students determine the "cis/trans" selectivity, turnover number, and maximum turnover frequency of the reaction. The experiment is conducted alongside the synthesis of stilbene using Wittig chemistry from a published procedure.
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