Undergraduate Organic Chemistry Research Articles

Special Issue Dedicated to Prof. Chien‐Hong Cheng's 70th Birthday

It is my great pleasure to announce that the special issue dedicated to Professor Chien-Hong Cheng on the occasion of his 70th birthday has been published. The total of 12 articles was collected in this issue, thanks to all the authors for their great contributions; also thanks to Professor Shih-Ching Chuang and Jen-Chieh Hsieh as well as the regular JCCS editorial board for their assistance. Professor Cheng is a world-renowned organometallic chemist. He has been conducting interdisciplinary research for many years and he has been mainly devoted to developing the transition metal-catalyzed new organic reactions and optoelectronic materials for many decades. His contributions impressed numerous people in both scientific and optoelectronic industrial communities. He developed many interesting organic transformations in sustainable pathways catalyzed by abundant transition metals. In addition to metal catalysis, the front cover of this issue demonstrates nicely the highlights of his research in organic light-emitting diode (OLED) display. He achieved a significant breakthrough in OLED technology by preparing new diboron illuminating materials in green OLED emitting layer. Its structure breaks through the world record of external quantum efficiency of the conventional OLEDs to about 38% with an efficiency roll-offof only 0.3% at 1000 cd/m2. Moreover, the cost is lowered down to a great extent. Because of his great research achievements, Professor Cheng was awarded many accolades and honors, and invited to deliver plenty of important lectures in international conferences. Professor Cheng was elected as an academician of Academia Sinica (AS) in 2018, which is the highest honor in academia in this country. It should be noted that during his forty-year (1979~2019) research and teaching career, he has grown many technology talents. He has delivered undergraduate inorganic chemistry and graduate organometallic chemistry to chemistry major students for a long time. The photo on the top of this page represents his achievement in training qualified personnel for academia and industry.

Environmentally Friendly Organic Chemistry Laboratory Experiments for the Undergraduate Curriculum: A Literature Survey and Assessment

Due to a growing awareness of environmental issues, green chemistry concepts are increasingly being incorporated into the undergraduate organic chemistry lecture and laboratory component. This minireview summarizes environmentally friendly organic chemistry experiments suitable for undergraduate laboratories. Whenever feasible, LD50 values for various chemicals are provided to allow readers to determine the suitability of an experiment for their curriculum based on the toxicity of reagents used.

Asymmetric Synthesis and Absolute Configuration Determination of an Enantioenriched Alcohol: A Discovery-Based Undergraduate Laboratory Experiment

An undergraduate organic chemistry experiment has been developed that features asymmetric synthesis of an enantioenriched secondary alcohol, followed by determination of its absolute configuration ...

CASE (Computer-Assisted Structure Elucidation) Study for an Undergraduate Organic Chemistry Class

Structure determination via NMR spectroscopy is a fundamental topic taught in many advanced level chemistry courses. Despite its importance as an analytical instrument, many students find the princ...

Apply for an undergraduate research fellowship

The American Chemical Society Division of Organic Chemistry is accepting applications for the 2020 Summer Undergraduate Research Fellowships. The $5,000 awards provide funding for summer research opportunities for outstanding undergraduate organic chemistry students attending colleges and universities in the US. Nominations are due Feb. 14. For more information, visit bit.ly/2NmZsUq.

A Multioutcome Experiment for the Williamson Ether Synthesis

Williamson ether experiments are commonly performed by students in undergraduate organic chemistry instructional laboratory courses. In this multioutcome experiment, students were provided 4-bromophenol and one of three alkyl halides: 1-bromopentane, 1-bromobutane, or 1-bromo-3-methylbutane. The alkyl halides served as the unknown component of the experiment, and students were given these three as unknown candidates. After isolating the product from the reaction mixture, students analyzed their products using FT-IR and benchtop 1H NMR spectroscopies. The experimental results herein summarize the inclusion of this experiment in the large enrollment second-semester organic chemistry laboratory course over four semesters.

Investigating perceptions of the structure and development of scientific knowledge in the context of a transformed organic chemistry lecture course

Organic Chemistry, Life, the Universe and Everything (OCLUE) is an undergraduate lecture-based organic chemistry course that has been transformed in line with the vision for science education set out by the ‘Framework for K-12 Science Education: Practices, Crosscutting Concepts and Core Ideas’ (National Research Council, 2012). OCLUE is designed to progress students understanding of core ideas in organic chemistry through the use of scientific practices such as constructing explanations, predictions and models. The purpose of this study is to generate theory on how OCLUE students conceptualise the structure and development of scientific knowledge. Eleven students with diverse experiences and exam performances were interviewed. The data was collected and analysed in accordance with the tenants of constructivist grounded theory (Charmaz, 2000). OCLUE students conceptualised a hierarchical structure of scientific knowledge whereby behind claims and answers in science is important information that determines the validity of the claim or answer. Being adept in utilising this information was important to students in OCLUE as it provided them with the opportunity to account for why phenomena occur in organic chemistry. Students explained that the process of developing scientific knowledge is rarely straight-forward or pre-determined. Instead it was believed that scientists needed to piece together what they know in seemingly random ways in order to solve science puzzles. In the context of OCLUE, students explained that memorising information ahead of OCLUE exams was insufficient. Instead they had to synthesise and interrogate their prior understanding to figure out new problems encountered in OCLUE exams. Students attributed the efficacy of OCLUE's pedagogy to helping them engage in constructivist thinking processes that involved interrogating and applying their prior knowledge. This contributes to the understanding that OCLUE has set out a precedent organic chemistry course that can foster a more scientific way of learning science that contrasts students’ engagement in considerably arduous memorisation techniques.

Computational Exercises in Undergraduate Organic Chemistry Laboratory

Computational Exercises in Undergraduate Organic Chemistry Laboratory

Teaching Organic Chemistry at the American University of Beirut Through the COVID-19 Pandemic

The COVID-19 pandemic has single-handedly overturned a traditional lecture-based educational system at universities on a global scale. The required abrupt move to an online platform for education has caused tremendous challenges for educational systems in general and specifically also in the chemical sciences. In Lebanon particularly, the COVID-19 pandemic raked havoc on a country entrenched in popular uprising and riddled by an economic collapse observing unprecedented devaluation of the national currency. In this situation, the move to online education had caused tremendous stress and burden for faculty and students raising the need to develop mitigation strategies by embracing reduction in material and a careful consideration of students’ mental health. This commentary presents the author’s experience of delivering undergraduate Organic Chemistry courses at the American University of Beirut (AUB) through the COVID-19 pandemic, during the spring and summer 2020 semesters. While the author’s pre-recorded lectures of Organic Chemistry I were vital to the online delivery of course material, this commentary particularly highlights the inclusion of supplementary online assignments that include: videos to illustrate a covered organic chemistry concept, instructional videos to explain a multiple choice question (MCQ) of their creation, a cartoon to exemplify an organic chemistry concept, a cartoon to reflect on studying organic chemistry during the COVID-19 pandemic and a group assignment that allowed students to assume social responsibility.

Support for instructional scaffolding with 1H NMR spectral features in organic chemistry textbook problems

Nuclear magnetic resonance (NMR) spectroscopy is vital to synthesis and provides rich problem-solving opportunities to organic chemistry students. Using the theories of scaffolding, interleaving, and blocking, our research systematically explores how textbooks introduce and reinforce spectral features when teaching students to solve 1H NMR spectroscopy problems. Specifically, we investigated the 1H NMR spectral features presented in worked examples and practice problems across four undergraduate organic chemistry textbooks. We examined the frequency and ordering of spectral features to explore how the textbooks could support scaffolded instruction. Spectral features like the number of signals and chemical shift were covered by problems more frequently, while integration was covered least. Our findings suggest that textbooks do not provide sufficient practice with all 1H NMR spectral features. We observed no discernible pattern in how textbooks ordered spectral features of 1H NMR in problems, indicating that there is little systematic method to the design of textbook chapters. Implications for textbook authors and editors, instruction, and research are discussed.

Demonstrating More Realistic Research Outcomes to Undergraduates in the Organic Teaching Lab: Separation of Product Mixtures, Structure Analysis, and Mechanistic Inquiry

How well does the undergraduate organic chemistry laboratory curriculum prepare students for academic research, or for a bench job in industry? Running experiments that are more representative of research chemistry has the potential to better equip students for working in a research laboratory, while at the same time giving them insight into a typical outcome in a research project. We describe here an experiment that we have launched in the sophomore organic chemistry lab at UC Davis that presents challenges in chromatographic separation, structural assignment by NMR, and mechanistic interpretation. Optional exercises in computational modeling of the NMR data and chromophore analysis by UV–vis/fluorescence measurements are included.

Implementing a Literature-Based, Problem-Solving Course Bridging Mechanistic Organic Chemistry, Enzyme Transformations, and Biomedical Applications

A chemistry course designed as an elective for chemistry, biochemistry, biology, and pharmaceutical science majors is described. The course is designed for second- through fourth-year undergraduate students. The prerequisite is first-semester, second-year undergraduate organic chemistry with the second semester of the organic sequence as a corequisite. The emphasis is on the mechanistic organic chemistry of enzyme transformations. An inductive approach is utilized in which students are initially taught an array of mechanistic probe experiments and learn how to design and implement these experiments to elucidate mechanisms. The intent of this research/hypothesis-driven approach is to enable students to propose experiments to test premises. After proposing probe experiments, the students will receive data so that, upon their interpretation of the data, they can propose potential mechanism(s) and defend their proposals. The primary chemical literature is emphasized throughout the course. Potential syllabi, a detailed overview of the applicable mechanistic probe experiments, multiple problem sets for distribution to students (with a faculty answer guide), a listing of 40 appropriate primary literature research articles utilized in the course, a listing of additional resources, and an extensive student study guide (reviewing applicable organic chemistry and biochemistry review principles) are all provided in the Supporting Information.

Carbohydrate Characterization through Multidimensional NMR: An Undergraduate Organic Laboratory Experiment

Carbohydrates are an essential group of molecules to the organic chemistry classroom providing molecular relevance to a common ingredient in chemical biology. While the meticulous elucidation of the carbohydrate structures by Fischer and others is an engaging topic in the lecture, there are few laboratory experiments that can emulate carbohydrate complexity. Advanced and multidimensional NMR (2D NMR) techniques such as correlation spectroscopies (COrrelation SpectroscopY (COSY), 13C Distortionless Enhancement by Polarization Transfer (DEPT), and HETeronuclear CORrelation (HETCOR) or Heteronuclear Single Quantum Coherence (HSQC)) have become more routine as they require less time on today’s instruments and are taught more often in lecture. A laboratory experiment is described for second-year introductory undergraduate organic chemistry students that involves the transformation of nutraceutical N-acetyl-d-glucosamine to α-chloroglucosamine tetraacetate. After synthesis and simple workup, students collect four different NMR spectra from which they identify each 1H signal in the product. Students learn to identify each signal’s multiplicity and how multiple NMR experiments are used to characterize a product. Student confidence in NMR characterization was assessed on a small subset through postlab questions and pre- and postsurvey data.

Thomas Bruice (1925–2019)

Thomas Bruice, one of the fathers of bioorganic chemistry, died on February 15, 2019, at the age of 93. He was born on August 25, 1925, in Los Angeles, California. He is survived by his wife, Paula Yurkanis Bruice, a renowned author of undergraduate organic chemistry textbooks. Thomas Bruice. Image courtesy of Tony Mastres (University of California, Santa Barbara, CA). The founding and maturing of the bioorganic chemistry field coincided with the golden era of physical organic chemistry, when chemists strove to describe the plausible mechanisms for organic reactions. Papers were being published that described novel methods for revealing the reaction’s kinetic coordinates, its stereochemistry, and for the detection of very short-lived, unstable intermediates. Biochemists were now in possession of the first enzyme crystal structures (urease, pepsin, chymotrypsin), but how did such proteins catalyze their reactions? Their active sites showed various candidates for acid/base chemistry but how did they act collectively? For the simple hydrolysis of amides and esters, the textbooks of that time showed their … [↵][1]1Email: sjb1{at}psu.edu. [1]: #xref-corresp-1-1

Microwave-Assisted Isolation of Eugenol from Cloves

An experiment for the undergraduate organic chemistry laboratory involving a method for the isolation of eugenol from cloves has been developed. The experiment employs microwave-assisted extraction (MAE) of the essential oil from whole cloves using aqueous ethanol and the subsequent isolation of eugenol by acid–base extraction. The MAE allows for extraction of the essential oil in a fraction of the time of steam-distillation, which is commonly part of a second-year undergraduate laboratory experience. The experiment combines multiple lab techniques and reinforces the introduction of spectroscopy in first-semester organic chemistry.

New, Milder Hypervalent Iodine Oxidizing Agent: Using μ-Oxodi(phenyliodanyl) Diacetate, a (Diacetoxyiodo)benzene Derivative, in the Synthesis of Quinones

The synthesis of substituted 1,4-benzoquinones, a biologically important class of compounds, was developed using μ-oxodi(phenyliodanyl) diacetate, a (diacetoxyiodo)benzene-based oxidizing reagent, in order to introduce second-year undergraduate organic laboratory students in their second semester or advanced organic students to increasingly popular and environmentally friendly hypervalent iodine chemistry. This experiment develops on concepts found in the undergraduate organic chemistry curriculum; conveniently fits into approximately two 3 h lab modules; and utilizes regularly found equipment and inexpensive, commercially available chemicals.

Synthesis of a Crosslinked Epoxy Resin Medallion in the Organic Chemistry Laboratory

Polymer synthesis has a limited inclusion in most organic chemistry lecture curricula, so emphasizing the concepts of polymer chemistry in a laboratory setting gives students hands-on experience in new content and broadens the scope of the class. The details and outcomes of a robust and well-developed laboratory procedure for the synthesis of a crosslinked epoxy network polymer are described. This experiment has been a part of a first-semester, introductory undergraduate organic chemistry laboratory curriculum for more than two decades and has positively impacted over eight hundred students. The experiment had the unique aspect that students cured the resin in a round, seven-centimeter mold, forming a hardened epoxy disk. This disk, or medallion, was decorated in two different ways: first, a design was etched into the mold before curing to form a permanent imprint; second, the final epoxy medallion was decorated, post-cure, with colored permanent markers and glitter glue. After this laboratory experiment, students took home a durable ornament as a memento of their first-semester organic chemistry laboratory course.

Synthesis Chalones and Their Isomerization into Flavanones and Azaflavanones.

Flavanones [2-aryl-2,3-dihydrochromen-4(1H)ones] and 2-aryl-2,3-dihydroquinolin-4(1H)-ones are valuable precursors in the synthesis of important pharmacological scaffolds, so efficient methodologies towards their synthesis are important in the medicinal chemistry context. Their synthesis also involves theoretical concepts such as aldol condensation, isomerization, and catalysis that make it useful in an undergraduate organic chemistry laboratory. The use of both microwave irradiation as a source of energy to promote reactions and efficient catalysts are considered within green chemistry principles, mostly because the reaction yields are improved and reaction time decreased. In this paper, the efficiency of microwave irradiation use in the synthesis of chalcone derivatives and efficient catalyst systems to promote their isomerization into flavanones and 2-aryl-2,3-dihydroquinolin-4(1H)-ones is demonstrated.

Using Retrosynthetic Graphic Organizers and Molecule of the Week Activities in Organic Chemistry Tutorials

The tutorials of a second-year undergraduate organic chemistry course have been modified to include a retrosynthetic exercise in conjunction with a Molecule of the Week (MoW) challenge. In contrast...

Improved Procedure for Bleach-Based Alcohol Oxidation in Undergraduate Laboratories

A reliable method for bleach-based alcohol oxidation has been developed. Use of sodium bisulfate as the acid additive in the reaction mixture eliminates the various problems associated with acetic acid, which has commonly been used for this type of oxidation. By conducting the reaction in an ethyl acetate/water two-phase reaction mixture, efficient reaction occurs at room temperature, and the workup is straightforward. This more reliable version of the well-known transformation has been successfully performed by thousands of second-year undergraduate organic chemistry students over the last several years.