The ability to reason with representations is pivotal for successful learning in Organic Chemistry and is closely linked to representational competence. Given the visual nature of this discipline, this comprises competency in extracting and processing relevant visual information. With regard to the resonance concept, proficiency in identifying…

Education in organic chemistry is highly reliant on molecular representations. Students abstract information from representations to make sense of submicroscopic interactions. This study investigates relationships between differing representations: bond-line structures, ball-and-stick, or electrostatic potential maps (EPMs), and predicting partial…

The ability to extract structural information from a drawing of a molecule is key to being successful in organic chemistry. One source of difficulty for novices in interpreting structures is that hydrogens bound to carbon are represented implicitly in the often-used line-angle structures. Other representations that explicitly show hydrogens, such…

Approximations can help to orient the student in an organic chemistry laboratory. There the student needs to develop the solvent systems for the reaction and isolation of organic reactants and products. The adage "like dissolves like" helps in this regard, but this approach is vague and entirely qualitative. More quantitative approaches…

Teaching the three-dimensional structure of saccharides has consistently been a challenging aspect of organic chemistry courses, impeding students' ability to grasp more advanced topics in biochemistry and food chemistry. In this article, we designed and developed a novel d-glucopyranose model using 3D printing technology for the first time. This…

Organic molecules are invisible objects, but they can be visualized and manipulated by using molecular models. The object-based learning (OBL) approach, which is an educational tool developed for museums and collection items, is tailored and applied to a first-year bachelor course of organic chemistry. At the beginning of the course, each student…

In this two-session experiment for an organic chemistry lab, students prepare a macrocyclic host compound--namely, a pillar[5]arene--by means of a templated 1,4-dimethoxybenzene/formaldehyde cyclo-oligomerization (session 1), and then, they explore its molecular recognition properties toward the 1,8-diaminooctane guest with the aid of [superscript…

Appealing to students' affect in academic settings, such as demonstrating chemistry's relevance to their life, is one strategy instructors may use to support students' in learning. This study investigates the types of connections that students make to organic chemistry when responding to an open-ended writing assignment. Students enrolled in an…

High-resolution mass spectrometry (HRMS) is an analytical technique that is typically used by mass spectrometry experts. However, with recent advancements, it is becoming more accessible to students in organic chemistry laboratories. Still, a significant knowledge gap exists between these experts and students. A straightforward laboratory…

Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe-Schmitt reaction), although aqueous, typically involves conditions…

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…

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…

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…

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,…

Interconverting different molecular representations can be problematic for many organic chemistry students. This is certainly the case when converting Fischer projections into bond-line structures. When performing the conversion from a Fischer projection into an all-staggered bond-line structure, students are sometimes taught to draw the fully…