Green Chemistry Decision-Making in an Upper-Level Undergraduate Organic Laboratory

Abstract

A self-directed independent synthesis experiment was developed for a third-year undergraduate organic laboratory. Students were provided with the CAS numbers of starting and target compounds and devised a synthetic plan to be executed over two 4.5 h laboratory periods. They consulted the primary literature in order to develop and carry out an azlactone synthesis incorporating green chemistry principles and techniques without detailed guidance from course instructors. Final products were analyzed via proton NMR spectroscopy, IR spectroscopy, and melting point analysis to determine if students were successful in forming their assigned material. Extremely positive feedback about the experiment was collected and is presented.

Synthesis of a Biologically Active Oxazol-5-(4H)-one via an Erlenmeyer–Plöchl Reaction

“…19 The observed lack of reactivity for aldehydes containing electron donating groups in the para position is consistent with the results of the Hammett equation (ρ = 0.91) for the involved reaction mechanism (see Supporting Information).…”

“…18 One way to measure the "environmental acceptability" of a given reaction or process is the calculation of an E-factor that quantifies the amount of waste generated per mass of product. 19 In the educational literature, the green chemistry concept has also been implemented, and the number of educational laboratory experiments published to introduce students to environmentally friendly reactions has been increasing. 20 The synthesis of 2-phenyloxazol-5(4H)-ones by the Erlenmeyer−Plochl reaction 21 is an example of an environ- Laboratory Experiment pubs.acs.org/jchemeduc mentally friendly reaction feasible in a teaching laboratory.…”

Sustainability in the Chemistry Curriculum: A Call for Action

“…Notably, this green chemistry supplement highlights the importance of systems thinking; that is, the need to view components as part of a greater whole, acknowledging the interactions among them . Additionally, recent journal articles and the references within them offer excellent resources for teaching and learning green chemistry …”

The Green Chemistry Initiative’s contributions to education at the University of Toronto and beyond

“…Through this program, several GCI members have successfully implemented green chemistry concepts into undergraduate classes, assignments, and teaching laboratories. As one example of this, Organic Synthesis Techniques (CHM 343H) is a third-year chemistry undergraduate course with an enrollment of 30-40 students per year (9,10). In 2014, a GCI member developed a novel assignment for CHM 343H that targets the use of industrial solvent and reagent selection guides (11)(12)(13)(14).…”