This paper describes a graduate-level class project centered on editing chemistry-related entries in Wikipedia. This project enables students to work collaboratively, explore advanced concepts in chemistry, and learn how to communicate science to a diverse audience, including the general public. The format and structure of the project is outlined and assessment metrics are discussed. A panel survey of current students provided an evaluation of the effectiveness of this project in contributing to the learning objectives of the course. Last, a discussion of the challenges involved in implementing this project is provided.

Research experiences are widely understood to be valuable for the intellectual and professional development of undergraduate science students. Course-based undergraduate research experiences (CUREs) have become popular as a means of engaging large numbers of students in research by leveraging institutional supports for laboratory courses. At Willamette University, we have adapted a guided-inquiry experiment that gave unexpected results into a CURE in the lower-division organic chemistry curriculum. This experience has engaged several cohorts of students in a 7 week investigation focused on identifying the mechanistic origin of a nonstereospecific hydroxybromination of Z-stilbene, an observation that contradicts how this addition reaction is presented in standard organic chemistry curricula. Each year, the cohort experimentally “discovers” the anomalous stereochemical outcome of the addition reaction. Students then participate in a workshop focused on developing mechanistic hypotheses that can account for the result and on designing experiments that will address their hypotheses. Over the next three lab sessions, students execute their experiments, reconsidering and revising their hypotheses as their data dictate. The experience culminates in formal oral and written presentations of results. Student perceptions of the pedagogical value of the CURE, the effect of the lab on their self-efficacy, and the novelty of research being conducted were assessed in multiple class cohorts, while faculty perceptions of changes in student behavior and skill were also documented.

A series of aryl trihydroxyborate salts were synthesized and found to form gels in benzene. The compounds were thermally unstable and readily underwent protodeboronation in solution and the solid state. Gelation could be induced without decomposition via sonication. Subsequent characterization studies revealed an unusual dependence of gel properties on alkyl chain length.

The electrochemical reduction of benzoate diesters of glycols has been studied in acetonitrile and N,N-dimethylformamide as solvents. The reductions occur in two closely spaced one-electron steps, and it was found that the dianion diradicals decompose by one of two routes, depending on the substituents on the ethylene moiety: cleavage of two benzoates to produce alkene or formation of benzil by way of a postulated cyclic intermediate to produce also the dianion of the diol. These correspond to cleavage of the R-OC(O)Ar bonds and the RO-C(O)Ar bonds, respectively. When the radical formed by the former cleavage is a primary or secondary radical, the reaction is too slow to compete with the latter reaction that produces benzil. However, when that radical is either tertiary or benzylic, the former cleavage reaction is fast and no benzil is detected. The dianions of p-cyano- and p-nitrobenzoate esters are rather stable on the voltammetric time scale. However, the addition of lithium ions results in detectable formation of 4,4'-dicyanobenzil from four different p-cyanobenzoate diesters.