While elimination reactions are ubiquitous in organic chemistry textbooks, their implementation in undergraduate laboratories still suffers from a lack of reliable and easy setup procedures. This paper describes an easy-to-implement set of elimination experiments in the pentanol and bromopentane series using a modified Hickman distillation head.…

Oxidation number (ON) is taught as an electron-counting concept for redox reactions in chemistry curriculum. The molecular formula method, the Lewis formula method, and the structural formula method have all been used to determine ON. However, the task of assigning ON still poses problems for some teachers and students. This paper explores a new…

A central practice in the discipline of organic chemistry is the ability to solve certain fundamental problems, including predicting reactivity, proposing mechanisms, and designing syntheses. These problems are encountered frequently by both students and practitioners, who need to utilize vast amounts of content knowledge in specific ways to…

Metal organic frameworks (MOFs) can have open pore structures with high surface areas and applications in hydrogen storage, carbon dioxide capture, water harvesting from air, chemical separations, and catalysis. The chemical structure of these crystalline solids can initially appear daunting. Simplification by considering the arrangement of the…

Spectroscopic characterization of molecules is typically reinforced in the organic chemistry teaching laboratory via the analysis of reaction products by NMR and IR, and initial coverage of these topics can include experiments involving the identification of unknown compounds. To combine the unknown identification component with common laboratory…

Science, technology, engineering, and mathematics (STEM) courses are considered to be challenging for students and may present unique challenges for each domain. This study addresses a gap in the research literature by investigating the challenges students face in general and organic chemistry lecture courses. Students provided information…

A discovery-based experiment for the synthesis of arylpropiolic acids via carboxylation of arylacetylenic Grignard reagents was developed. This experiment shows the "dual utility" of Grignard reagents. In the synthesis of arylpropiolic acids reported here, we have demonstrated the use of a Grignard reagent as a base in a "Grignard…

The acid-catalyzed dehydration of regioisomeric methylcyclohexanols is a classic organic chemistry experiment featured in a variety of laboratory textbooks and literature. The mechanistic details of this reaction have received an inconsistent and occasionally inaccurate treatment, wherein the reaction has been described as a mix of E1, E2-like,…

The work presented in the following chapters was undertaken with the goal of understanding and improving education in organic chemistry. Initial work, described in Chapters 1 and 2, focuses on students' ability to explain and rationalize the outcomes of organic chemistry reactions. Chapter 1 explores the relationship between assessment emphasis…

Resonance is a fundamental chemistry concept first introduced to students in General Chemistry I, reintroduced in Organic Chemistry I, and then utilized throughout other higher-level chemistry courses. A molecule or ion can be said to exhibit resonance when it can be represented by two or more chemical structures (i.e., Lewis structures) that…

Offering an advanced organic chemistry course at a primarily undergraduate institution poses a challenge of condensing graduate organic synthesis into one course. This course was designed so students choose and read recent total synthesis papers from the literature in lieu of relying on a textbook or other pre-existing course materials. Following…

S[subscript N]2 reactions are of fundamental importance in introductory organic chemistry courses, and a number of experiments suitable for the first-semester undergraduate organic lab have been previously reported. Most of these experiments have used alkyl halides as electrophiles, but alkyl halides are often less than ideal for reasons of…

Discussions of the primary literature are an important part of undergraduate education, and much work has been done to develop methods of integrating the literature into the curriculum. Examples include individual single-article discussion activities, literature-based courses, and regular journal club events. While many published examples focus on…

A [beta]-lactam, the core structure unit of clinically important antibiotics such as penicillin and cephalosporin, is one of the most commonly encountered four-membered heterocycles in organic chemistry and is widely used in medicine and biochemistry. The Kinugasa reaction, a copper­(I)-catalyzed cycloaddition of a terminal alkyne with a nitrone,…

Here we showcase an undergraduate teaching laboratory in which students synthesize and characterize colloidal nanoparticles of organic semiconductors and assess their suitability for applications in printed electronics such as solar cells and bioelectronics. Scanning electron microscopy, UV-visible spectroscopy, and photoluminescence spectroscopy…