In undergraduate chemistry curricula that include computational modeling, students may gain first-hand experience in both introductory and advanced applications of this technique. However, although students can be exposed to the predictive power of computational work, its capabilities are often limited to determining the intrinsic properties of…

This communication describes a variety of virtual student assessment strategies employed at the University of Toronto during the academic disruption caused by the 2020 COVID-19 global pandemic. Instructors focused their efforts toward maintaining a positive learning environment and offering meaningful evaluation methods for students in each of…

The Chemistry Teaching Fellowship Program (CTFP) is offered to graduate students and postdoctoral researchers at the University of Toronto as an opportunity to undertake curriculum development and chemistry education research. Projects are run with faculty supervision and focus on designing new laboratory activities, lectures, tutorials,…

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…

The ability of science undergraduate students to capably communicate course content and their understanding of scientific phenomena through writing has long been considered a problem. Effective methods for improving student writing skills are often fragmented and undertaken on a course-by-course basis rather than as a coordinated approach. This…

A synthetic procedure is outlined where upper-level undergraduate organic chemistry students perform a two-week, semimicroscale "aza"-Baylis-Hillman reaction to generate an allylic sulfonamide product. Students evaluate several green chemistry reaction metrics of industrial importance (process mass intensity (PMI), E factor, and reaction…

NMR spectroscopy has great potential as an instrumental method for environmental chemistry research and monitoring but may be underused in teaching laboratories because of its complexity and the level of expertise required in operating the instrument and interpreting data. This laboratory experiment introduces environmental NMR spectroscopy to…

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…

This article describes the organic chemistry of five compounds that are directly associated with the Christmas season. These substances and related materials are presented within the framework of the five senses: silver fulminate (sound), alpha-pinene (sight), sodium acetate (touch), tryptophan (taste), and gingerol (smell). Connections with the…

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…

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…

An introductory organic classroom demonstration is discussed where analogies are made between common societal hand contact and covalent bond formation. A handshake signifies creation of a [sigma] bond ("head-on" orbital overlap), whereas the action of praying illustrates "sideways" overlap and generation of a [pi] bond. The nature of orbital and…

An upper-level mechanistic organic experiment is outlined where undergraduates measure kinetic rate constants for decarboxylation of pyrrole-2-carboxylic acid by the initial-rates method. UV spectroscopy is used to monitor reactant disappearance in both hydrochloric acid and deuterium chloride at different temperatures. Individual data are pooled…

A short, semi-microscale synthesis of two 1,4-dihydropyridine drug analogues via a Hantzsch reaction is described, which is appropriate for a second-year undergraduate organic laboratory. Products are specifically chosen to highlight the biological relevance of this compound type while introducing the notion of a privileged structure.…