In order to introduce the concepts of biocatalysis and its utility in synthesis to organic chemistry students, a multistep synthesis of endogenous cannabinergic ligand 2-arachidonoylglycerol (2-AG) was tailored for use as a laboratory exercise. Over four weeks, students successfully produced 2-AG, purifying and characterizing products at each…

As nonrenewable resources deplete and educators seek relevant interdisciplinary content for organic chemistry instruction, biobased laboratory experiments present themselves as potential alternatives to petroleum-based transformations, which offer themselves as sustainable variations on important themes. Following the principles of green chemistry…

A problem-solving scaffold approach to synthesis was developed and implemented in two intervention sections of Chemistry 2211K (Organic Chemistry I) at Georgia Gwinnett College (GGC). A third section of Chemistry 2211K at GGC served as the control group for the experiment. Synthesis problems for chapter quizzes and the final examination were…

Students often struggle with solving mechanism problems in organic chemistry courses. They frequently focus on surface features, have difficulty attributing meaning to symbols, and do not recognize tasks that are different from the exact tasks practiced. To be more successful, students need to be able to extract salient features, map similarities…

The first-semester introductory organic chemistry laboratory has been adapted to include mini postlab assignments that students must complete correctly, through as many attempts as prove to be necessary. The use of multiple drafts of writing assignments is a standard approach to improving writing, so the system was designed to require drafts for…

The traditional assignment of oxidation states to organic molecules is problematic. Accordingly, in 1999, Calzaferri proposed a simple and elegant solution that is based on the similar electronegativities of carbon and hydrogen: hydrogen would be assigned an oxidation state of zero when bonded to carbon. Here, we show that X-ray photoelectron…

A laboratory experiment is described that extracts the tetrapyrrolic teal-colored biliverdin IXa, as its dimethyl ester, from commercially available emu eggshells. The extraction of ~10 mg samples of biliverdin is simple and requires two 3 h lab periods: A two-step acid digestion and liquid-liquid extraction, followed by short silica gel flash…

When new concepts, models, or theories are introduced in a course, their presentation should be accurate, even if depth is not the goal. In a recent publication in this Journal, the Woodward-Hoffmann rules were invoked in the context of a new laboratory experiment, but the associated description was inaccurate. Here we aim to clarify the…

Sense of smell is one of the important senses that enables us to interact with our environment. The molecular basis of olfactory signal transduction is a fascinating area for organic chemistry educators to explore in terms of developing undergraduate laboratory activities at the interface of chemistry and biology. In this paper, a guided-inquiry…

Mastering the ability to construct and manipulate Lewis structures is an important first step along the journey to reaching representational competence. Lewis structures serve as a convenient organizational scheme that can help students to scaffold their chemical knowledge and help them to apply it to predict a variety of physical and chemical…

Web-based classroom response systems offer a variety of benefits versus traditional clicker technology. They are simple to use for students and faculty and offer various question types suitable for a broad spectrum of chemistry classes. They facilitate active learning pedagogies like peer instruction and successfully engage students in the…

A green, aza-Michael reaction is described that can be used to teach undergraduate students conjugate addition of nitrogen nucleophile to an a,ß-unsaturated ester. Students analyze spectral data of the product obtained from the assigned reaction to determine product structure and propose the mechanism of its formation. The experiment requires…

This study describes the development and application of a three-tier test as a valid and reliable tool in diagnosing students' misconceptions regarding some basic concepts about carbohydrates. The test was administrated to students of the Pharmacy Department at the University of Bijeljina (Serb Republic). The results denoted construct and content…

A simple, microscale experiment was developed with the aim of demonstrating the concept of umpolung in synthetic organic chemistry. Starting from a common alkyl sulfinate, students perform a polarity inversion by performing a Grignard-based sulfoxide synthesis and a Mannich-type formamide synthesis. The products are purified without chromatography…

A significant redesign of the introductory organic chemistry curriculum at the authors' institution is described. There are two aspects that differ greatly from a typical functional group approach. First, organic reaction mechanisms and the electron-pushing formalism are taught before students have learned a single reaction. The conservation of…