This study explored what cognitive resources (i.e., units of knowledge necessary to learn) first-semester organic chemistry students used to make decisions about acid strength and how those resources guided the prediction, explanation and justification of trends in acid strength. We were specifically interested in the identifying and…

The nature of laboratory work has changed in the past decade. One example is a shift from working individually or in pairs on single traditional verification experiments to working collaboratively in larger groups in inquiry and research-based laboratories, over extended periods in and outside of the lab. In this increased era of collaboration, we…

This laboratory experiment was developed to provide a safe, economical, and effective way to instruct undergraduate organic chemistry students about the unimolecular nucleophilic substitution (S[subscript N]1) reaction. Students treat 2,5-dimethyl-2,5-hexanediol with excess concentrated hydrochloric acid to synthesize…

An instructional method is described that was used in a large, introductory organic chemistry course to ask online, post-class questions and to use the students' answers to design the lesson and learning activities for the following class. Additional goals of this method were to provide relevant, regular, and prompt feedback to students and the…

Chiral oxazolidinone chemistry is used as a framework for an advanced multi-step synthesis lab. The cost-effective and robust preparation of chiral starting materials is presented, as well as the use of chiral auxiliaries in a synthesis scheme that is appropriate for students currently in the second semester of the organic sequence. (Contains 1…

A major approach for implementing green chemistry is the discovery and development of synthetic strategies that reduce the quantity of solvent needed, eliminate it altogether, or rely on new reaction media. An increasing number of examples have demonstrated that greener reaction solvents or media can enhance performance as well as reduce hazard.…

A critical stage in the process of developing a conceptual understanding of organic chemistry is learning to use curved arrow notation. From this stems the ability to predict reaction products and mechanisms beyond the realm of memorization. Since evaluation (i.e., testing) is known to be a key driver of student learning, it follows that a new…

Water is the ideal green solvent for organic reactions. However, most organic molecules are insoluble in it. Herein, we report a laboratory module that takes advantage of this property. The Passerini reaction, a three-component coupling involving an isocyanide, aldehyde, and carboxylic acid, typically requires [similar to] 24 h reaction times in…

A series of experiments involving the synthesis and characterization of a benzene-1,3,5-tricarboxamide derivative and its self-assembly properties are reported. These laboratory experiments combine organic synthesis, self-assembly, and physical characterization and are designed for upper-level undergraduate students to introduce the topic of…

The generally accepted method to determine iron content in food is by acid digestion or dry ashing and subsequent flame atomic absorption spectrometry or inductively coupled plasma atomic emission spectrometry. We have developed an experiment that chemically extracts the iron from an egg yolk and quantifies it using UV-vis absorption…

The original use of the prefix "meso" was to refer to an optically inactive, non-resolvable member of a set of stereoisomers, some of which were optically active. More recently there have been attempts to define meso in terms of the structural features that can account for the existence of meso forms. It is unlikely that an effort of this kind…

In this article I review one of the most significant accomplishments of Frank H. Westheimer, one of the most respected chemists of the 20th century. This accomplishment was a series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize what we now call the enantiotopic and diastereotopic relationships of…

Research about motivation indicates that a student's attention must be gained and sustained for learning to occur. As a result, motivational tactics, including adding interesting words, sounds and visuals to instructional materials, are commonly used by designers of instruction to trigger and sustain learners' interest and engagement…

This study examined the historical performance of students at Michigan State University in a two-part biochemistry series Biochem I (n = 5,900) and Biochem II (n = 5,214) for students enrolled from 1997 to 2009. Multiple linear regressions predicted 54.9-87.5% of the variance in student from Biochem I grade and 53.8-76.1% of the variance in…

Stereochemistry is an important topic in organic chemistry. It is also a difficult topic for students to learn. This study investigated the relative effectiveness on students' understanding of three kinds of molecular representations of stereochemistry concepts. Instructional activities compared the use of either: (i) computer-based molecular…