Title

Synthesizing Stilbene by Olefin Metathesis Reaction Using Guided Inquiry to Compare and Contrast Wittig and Metathesis Methodologies

Document Type

Article

Date of Original Version

1-8-2019

Abstract

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 1H 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.

Publication Title

Journal of Chemical Education

Volume

96

Issue

1

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