A method for the synthesis of ibuprofen in introductory organic chemistry laboratory courses is reported. This experiment requires two 3-h lab sessions. All of the reactions and techniques are a standard part of any introductory organic chemistry course. In the first lab session, students reduce p-isobutylacetophenone to an alcohol and then…

Western red cedar leaf affords an essential oil characterized by high thujone content. Students in an advanced organic chemistry lab course isolate a single thujone diastereoisomer from commercially available cedar leaf oil. Treatment of crude oil, containing roughly 70% thujone, predominately as [alpha]-thujone (6.5:1), with ethanolic sodium…

This laboratory experiment exposes students to the chemistry of self-healing polymers based on a Diels-Alder reaction. Students accomplish a multistep synthesis of a monomer building block and then polymerize it to form a cross-linked polymer. The healing capability of the polymer is verified by differential scanning calorimetry (DSC) experiments.…

Although transition-metal-catalyzed reactions are important in contemporary organic chemistry, relatively few resources for the second-year organic chemistry curriculum discuss the subject. The inquiry-based experiment described here, an iron-catalyzed preparation of biphenyl from bromobenzene, introduces this topic. The reaction uses an…

The Grignard reaction and the addition of protecting groups are standard reactions in an organic chemistry course. Organic students learn about the "quench" step of the Grignard reaction using acid and water and the acid-catalyzed hydrolysis to remove the protecting group, yet in the lecture students find these two reactions to be confusing in…

Normal-phase chromatography is an essential technique for monitoring chemical reactions, identifying the presence of specific components, as well as the purification of organic compounds. An experiment to facilitate the instruction and understanding of the concepts behind normal-phase chromatography at the introductory and intermediate…

Inverted teaching, not to be confused with hybrid learning, is a relatively new pedagogy in which lecture is shifted outside of class and traditional homework is done in class. Though some inverted teaching (IT) designs have been published in different fields, peer-reviewed reports in university chemistry remain quite rare. To that end, herein is…

Lantibiotics are cyclic peptides that exhibit a range of biological properties, including antimicrobial activity. They are ribosomally-synthesized as linear precursor peptides that consist of two regions, an N-terminal leader peptide and a C-terminal propeptide (or structural) region. The structural region undergoes extensive enzyme-catalyzed…

We describe accommodations that we have made to our applied computational-theoretical chemistry laboratory to provide access for blind and visually impaired students interested in independent investigation of structure-function relationships. Our approach utilizes tactile drawings, molecular model kits, existing software, Bash and Perl scripts…

This paper examines the impact of supplemental instruction (SI)--nonremedial workshops that support regularly scheduled courses--on four different chemistry courses: General Chemistry I and II, and Organic Chemistry I and II. Differences in how SI impacts student performance in these courses are discussed, particularly in terms of whether students…

A novel stereochemistry lesson was prepared that incorporated both handheld molecular models and embedded virtual three-dimensional (3D) images. The images are fully interactive and eye-catching for the students; methods for preparing 3D molecular images in Adobe Acrobat are included. The lesson was designed and implemented to showcase the 3D…

Understanding of the nature of science is key to the development of new curricular materials that mirror the practice of science. Three problem types (project level, synthetic planning, and day-to-day) in synthetic organic chemistry emerged during a thematic content analysis of the research experiences of eight practising synthetic organic…

Innovative, research-based instructional practices are critical to transforming the conventional undergraduate instructional landscape into a student-centered learning environment. Research on dissemination of innovation indicates that instructors often adapt rather than adopt these practices. These adaptations can lead to the loss of critical…

The "Organic Chemistry in Action!" ("OCIA!") program is a set of teaching resources designed to facilitate the teaching and learning of introductory level organic chemistry. The "OCIA!" program was developed in collaboration with practicing and experienced chemistry teachers, using findings from Chemistry Education…

Distillation is a ubiquitous technique in the undergraduate organic chemistry curriculum; the technique dates back to ca. 3500 B.C.E. With the emergence of green chemistry in the 1990s, the importance of emphasizing responsible waste management practices for future scientists is paramount. Combining the practice of distillation with the message…