This article describes the successful implementation of an oral examination format in the organic chemistry curriculum at the University of Toronto. Oral examinations are used to replace traditional written midterm examinations in several courses. In an introductory organic class, each student is allotted 15 min to individually discuss one pre-selected "named" reaction with the course instructors. To stimulate further learning, students must choose a particular reaction that has not been presented during lecture or performed in the laboratory. In upper-level courses, students review selected literature syntheses of either a drug molecule or natural product. The oral examination format provides a dynamic assessment approach that can be individualized to facilitate an in-depth analysis of student comprehension.

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.

An upper-year undergraduate practical examination is presented that utilizes the EcoScale (a semiquantitative tool) and several established mass metrics to assess student understanding of green chemistry principles. This activity focuses on the straightforward preparation of a benzodiazepine via three different catalytic methods, and the analysis of individual experimental data during laboratory time. Students learn about the structure of the EcoScale, apply it as a simplistic life cycle assessment, and critique it as a scientific model. The examination complements more traditional expository and self-design experiments within a synthetic course where green chemistry and sustainability are central themes. ARTICLE HISTORY

Students prepare a tertiary amine antifungal analog in an upper-level undergraduate organic laboratory. A microscale Petasis reaction is performed to generate a liquid compound readily characterized via IR and proton NMR spectroscopy. The biological relevance of the product is highlighted, with the tertiary amine scaffold being an important treatment option for resistant bacterial and fungal infections. The procedure allows for postlaboratory discussion of nitrogen as a stereocenter in an ammonium ion, along with principles of combinatorial chemistry and green chemistry. Deliberation of potential mechanisms for the Petasis reaction provides another valuable learning opportunity for students.

This article describes the integration of a cocurricular "Community" into a first-year undergraduate chemistry course at the University of Toronto. The Community has been in existence since 2006, with over 700 students being involved. Its broad objectives have been three-fold: to inform course members about departmental resources and their significance, to teach skills and provide tips away from formal class content, and to promote the importance of undergraduate research/highlight available opportunities. The Community has received very positive feedback over a number of years and has resulted in a large increase in the number of students enrolling in second-and fourth-year undergraduate science research courses.