Although the principles of green chemistry have been well-defined for almost two decades, very little green chemistry has made its way into traditional organic chemistry textbooks. This allows for an opportunity in the organic chemistry laboratory to introduce new green chemistry experiments in a guided-inquiry based fashion. Use of green reaction conditions in the lab can thus be used to serve two purposes: 1) to introduce students to the principles of green chemistry and 2) to better simulate a research environment, where experiments are conducted in order to test a hypothesis, rather than to obtain a pre-determined result. Two experiments were developed that demonstrate green chemical principles and address electrophilic additions to pi bonds, a key topic in the first semester of organic chemistry. The addition of bromine to trans-cinnamic acid using in situ generation of bromine in an alcohol solvent is described. The hydration of phenylacetylene using a gold catalyst to replace the standard mercury-catalyzed reaction is also discussed. Product analyses for both experiments are accomplished using a variety of physical and spectroscopic techniques, allowing the experiments to be adapted to many laboratory environments.

Green chemistry as a basis for developing guided-inquiry experiments for the undergraduate organic chemistry laboratory

247th National Meeting (2014)

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