Mechanochemistry is maturing as a discipline and continuing to grow, so it is important to continue understanding the rules governing the system. In a mechanochemical reaction, the reactants are added into a vessel along with one or more grinding balls and the vessel is shaken at high speeds to facilitate a chemical reaction. The dielectric constant of the solvent used in liquid-assisted grinding (LAG) and properly chosen counter-ion pairing increases the percentage conversion of stilbenes in a mechanochemical Wittig reaction. Utilizing stepwise addition/evaporation of ethanol in liquid-assisted grinding also allows for the tuning of the diastereoselectivity in the Wittig reaction.

Green chemistry and sustainability have garnered more awareness in the chemical industry in recent years, but green chemistry classes are still not commonplace for either the undergraduate or graduate student curriculum. Additionally, many departments are seeking avenues to reach greater numbers and types of learners through online courses. To address both needs, a small group of chemistry graduate students set out to design a 3-credit-hour upper-level online green chemistry course targeted at students most likely to apply green chemistry concepts in their future careers. The goals for the course included education in the basics of green chemistry (history, metrics, methodologies) along with opportunities to apply what they have learned and communicate it to a general audience. This process of developing modules and assessments for the discovery and application of green chemistry principles has enabled a supplementary education for the graduate students as well. Herein, the specific motivations of the graduate students to design the course, how green chemistry was presented to students in an online format, and how students responded to this type of class are provided.

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The oxidation of primary alcohols under mechanochemical conditions in a Spex8000M Mixer/Mill was investigated. To facilitate ease of separation and recyclability, a polystyrene-bound version of a TEMPO catalyst was employed. When paired with Oxone® in a stainless-steel vial with a stainless-steel ball, several primary alcohols were successfully oxidized to the corresponding carboxylic acids. The product was isolated using gravity filtration, which also allowed for the polystyrene-bound TEMPO catalyst to be recovered and reused in subsequent oxidation reactions. Furthermore, it was demonstrated that the size and steric hindrance of the primary alcohol does not hinder the rate of the reaction. Finally, the aldehyde was selectively obtained from a primary alcohol under ball milling conditions by using a combination of non-supported TEMPO with a copper vial and copper ball.

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