Advances in Teaching Organic Chemistry

Organizer: Susan F. Hornbuckle, Department of Natural Sciences, Clayton State University, 2000 Clayton State Blvd., Morrow, GA 30260, tel: (678) 466-4780, Email: SusanHornbuckle@clayton.edu

In the morning session, Michael J Castaldi, Saint Peter's College, presented Undergraduate organic chemistry research on a shoe-string budget. This presentation focused on the challenges and successes of undergraduate organic chemistry research in a small inner-city private college. After no research in more than 10 years, the presenter and his colleagues revived the undergraduate research program with projects in organic and medicinal chemistry. Lack of instrumentation and chemicals posed a challenge. However, 50% of the students from the first semester chose to continue their research the following semester. Jane E Wissinger, University of Minnesota, presented Oxidation of borneol to camphor using Oxone® and catalytic NaCl: A green experiment for the undergraduate organic chemistry laboratory. A new green oxidation procedure was developed for the undergraduate organic teaching laboratories for use by over 1000 students per year. The experiment was performed using (1S)-borneol providing large quantities of the less prevalent (1S)-camphor which is useful in a research setting. The product was analyzed using IR and NMR. Nagarajan Vasumathi, Jacksonville State University, presented Undergraduate research as a teaching tool in organic chemistry. The presenter discussed the importance of providing students with the tools to understand the fundamental “language” of organic chemistry and to appreciate the art, elegance and creativity involved in synthetic organic chemistry. Studies on PABA ester synthesis and product characterization was discussed as a model.

Stacy A. O'Reilly, Butler University, presented Catalyzing connections between synthetic experiences: Using a copper-hydride catalyzed reduction to build bridges. Methods of how can we make better connections between organic lab and a more advanced synthetic lab were discussed. Using synthetic modules such as the synthesis of silyl ethers involved the students in research design, methodology, workup, and analysis. This procedure was used to help students make a better transition into the research lab. John J. Esteb, Butler University, presented Development of a microwave-assisted Diels-Alder reaction for the undergraduate organic laboratory: Meshing modern techniques with classic reactions. A microwave-assisted Diels-Alder synthesis of substituted cyclohexenols experiment developed for use in the undergraduate organic teaching laboratory was discussed. The experiment lends itself well to an approach where a variety of related products can be made through systematic variation of the dieneophile/diene combinations. Iyun Lazik, Christopher Connelly, and Olivia Sanchez, San Jose City College, presented Fermentation and biofuel research of wild mustard (Brassica campestris): A native californian flora as a potentially viable source of ethanol production. This presentation focused on the redesign of a sophomore organic chemistry laboratory class to a more active learning experience with real-life applications. The topic of biofuel was used as basis for discussion on carbohydrates, acid hydrolysis, and fermentation. Students did literature research, collected various plant materials, designed and preformed experiments for ethanol production, and analyzed the effectiveness of each process. C. Eric Ballard. University of Tampa, presented Green reductive homocoupling of bromobenzene. This presentation focused on using the sophomore organic chemistry laboratory to introduce topics absent in organic chemistry textbooks. For example, although transition metal-catalyzed reactions are important in contemporary chemistry, relatively few resources for the sophomore organic chemistry curriculum discuss the subject. The author discussed the use of an inquiry-based experiment of an iron-catalyzed preparation of biphenyl to introduce redox cycles common in many metal-catalyzed reactions, redox processes of organic substrates, and green chemistry.

Yi Pan, City College of New York, presented Convenient method for the synthesis of cinnamaldehyde.  This presentation focused on a one-step synthesis of cinnamaldehyde that was used in a senior level laboratory course where students were studying organic chemistry and practicing organic synthesis skills. One possible variation of the synthesis experiment above was a four-session experiment that included: (a) separation of cinnamaldehyde from nature product cinnamon sticks; (b) chemical synthesis, characterization, and structure elucidation of cinnamaldehyde using 1HNMR, FT-IR, and GC-MS. The two-session experiment may only include the part (b). Students will learn the basic organic skills such as extraction, isolation, synthesis, and identification techniques. Then, John A. Cramer, Seton Hill University, presented Multiweek exercises in the organic chemistry laboratory course: An effective means for enhancing student experimental competency. This presentation focused on the isolation and characterization of orange oil as a six-week project that requires students to multitask and problem solve in lab. This multiweek exercise required the coordinated use of a wide range of experimental protocols, including the analysis of data from the chemical literature, and serve to promote active learning, multitasking, and collaborative learning skills.

In the afternoon session, Susan M Schelble, Metropolitan State College of Denver, presented Outcomes from the use of a collaboratively developed organic chemistry practice exam. This presentation focused in the development process for a practice exam for the ACS exam for Organic Chemistry. Question types as well as determination of question validity were discussed. Gary M Battle, Cambridge Crystallographic Data Centre, presented Using experimentally-measured crystal structures to teach organic chemistry concepts. This presentation focused on the use of crystal structure data from the Cambridge Crystallographic Database in teaching organic chemistry. Crystal structures were discussed as a means of exemplifying fundamental concepts such as stereochemistry, conformation, and chirality. When analyzed collectively, these provide a wealth of knowledge that serve to support reaction theories and mechanistic details. Examples from the Cambridge Crystallographic Database were presented. Jonathan H. Chen, University of California, Irvine, presented Reaction Explorer: Organic chemistry tutorial system with inherent predictive power and collaborative learning support. This presentation focused on “Reaction Explorer” an interactive tutorial system for organic chemistry that can generate a virtually limitless number of multi-step synthesis design and reaction mechanism problems with support for inquiry-based learning. Two alternative formats (Chemical Company Format and Tetris Format) were also presented. R. Daniel Libby, Moravian College, presented Teaching course content and data processing skills along with laboratory techniques in the organic laboratory. The presenter discussed his approach to sophomore organic chemistry laboratory, which employs large student-acquired data sets, helps students learn course content, data processing skills and scientific writing skills while they are acquiring laboratory techniques. Alicia A. Peterson, College of St. Benedict/St. John’s University, presented Evolution of an introductory organic chemistry course. The presenter discussed the redesign of their sophomore organic chemistry course away from the typical functional group study to a topic/reaction type approach. First semester topics included spectroscopy, nomenclature (outside of class), conformations, stereochemistry, MO theory, acid – base chemistry, and Sn1, Sn2, E1, E2 reaction types. Second semester topics included applications of substitution reactions, alpha-alkylation, nucleophilic addition, aldol reactions, and nucleophilic substitution.

Chris P. Schaller, College of St. Benedict/St. John’s University, presented Developing complex problem solving skills with modern applications of reactivity. The presenter discussed the use of a workbook to deliver in-class problems. Problems not worked in class were to be worked outside of class. The workbook was used to develop skills in key areas of organic chemistry such as synthesis, mechanism, data analysis, relative rates, spectroscopy and mechanistic analysis. Ryan Denton, Indiana University Purdue University Indianapolis, presented Implementing problem-solving discussion sections in the first semester organic chemistry lecture. The presenter discussed an attempt to improve student engagement and address declining exam performance, a less than desirable DFW rate, and negative student perceptions, through a problem-solving Peer-Led Team Learning (PLTL) discussion section. Initial results indicate minimal effect on course exam performance or ACS exam scores. Then, Jacqueline Bennett, SUNY College at Oneonta, presented Beyond multiple choice: Using clickers to ask high-level questions in organic chemistry. The presenter discussed the pros and cons of using clickers in a Sophomore Organic Chemistry course. Then, she focused on methods of developing more sophisticated clicker questions that require a deeper understanding of the material. Examples of the various levels of clicker questions were shared with emphasis on multi-step synthesis and proton NMR questions.

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