In this paper, we present a concise and technique-heavy route to the synthesis of dimedone for a second-year organic chemistry curriculum. Our preparation of dimedone guides students through a Michael addition followed by a Dieckmann cyclization, basic ester hydrolysis, and thermal decarboxylation, while allowing time for mechanistic discussion…

The synthesis of a [2]rotaxane through three- or five-component coupling reactions has been adapted to an organic chemistry experiment for upper-division students. The experimental procedure addresses the search for the most favorable reaction conditions for the synthesis of the interlocked compound, which is obtained in a yield of up to 71%.…

An understanding of basic organic chemical reactivity is key for many biosciences students. The reactivities of different carbonyl groups affect their function in many biomolecules. A practical class, the two-step synthesis of paracetamol, has been devised to illustrate the electrophilic reactivities of carbonyls, which was covered in the…

Background: Science teaching and learning, as discursive practices, occur through the utilization of various semiotic modes. Gestures play a pivotal role as an embodied mode that acts in conjunction with speech in oral communication settings, such as classrooms. Previous research on gestures in chemistry and science education has illuminated how…

General chemistry courses serve as foundational curriculum within most STEM undergraduate curricula, and hence, it is essential to assess student knowledge and application of learning outcomes for courses such as Introduction to Chemistry and Organic Chemistry. Within the United States, paper-and-pencil examinations are typical for measuring…

Students' view of intelligence (i.e., their mindset beliefs) has been found to be related to their self-efficacy and goal orientations as well as to influence their course outcomes. Comparisons of students' chemistry mindset between different groups found that organic chemistry I students held more of a growth mindset than general chemistry I…

A multistep synthesis of a novel arylidene 3­(2"H")-furanone has been designed and optimized for the second-year organic laboratory. The three-step sequence consists of a nucleophilic substitution, intramolecular cyclization, and acid-catalyzed aldol condensation, and can be carried out within two 3 h laboratory periods. The final…

Historically, deaf and hard-of-hearing students (D/HH) who solely rely on an interpreter during organic chemistry lecture courses at the Rochester Institute of Technology consistently performed below the average in the class. A barrier attributed to this D/HH student performance is the lack of standardized methods in sign language to effectively…

The goal of this study was to evaluate the effectiveness of organic chemistry textbooks in developing student representational competence skills with eight representations of molecular structure (Lewis structures, Kekulé structures, condensed structures, electrostatic potential maps, skeletal structures, dash-wedge diagrams, Newman projections,…

Educational games have consistently proved that they are valuable didactic instruments, which can contribute to teaching and learning in an enjoyable background. In organic chemistry courses, considerable effort has been made to encourage the learning of nomenclature, an important topic, often perceived as complex, boring, and unconnected to other…

As electrochemistry continues to gain broader acceptance and use within the organic chemistry community, it is important that advanced undergraduate students are exposed to fundamental and practical knowledge of electrochemical applications for chemical synthesis. Herein, we describe the development of an undergraduate laboratory experience that…

Substitution reactions of alcohols are some of the simplest experiments performed in undergraduate organic chemistry laboratory settings. However, the use of gas chromatography (GC) as an analytical tool for these reactions can be at times laborious and time-consuming. In this work, 1-pentanol, 2-pentanol, 3-pentanol, and 2-methyl-2-butanol were…

We have developed a course-based undergraduate research experience (CURE) that can be carried out in the context of an existing second-semester or upper-level organic laboratory course. In this three-week laboratory module, students synthesize a small library of molecules, test them in a robust biological assay, and design a new compound library…

An operationally simple, reliable synthesis of ethynylated acenes suitable for an upper-division undergraduate organic chemistry laboratory course has been developed. This experiment requires students to synthesize two acene derivatives and can be completed in 6-8 laboratory sessions (3 h each); a shorter experiment could be realized in the…

Multicomponent reactions (MCRs) represent very interesting tools to reach eco-friendly and sustainable transformations in organic chemistry. In particular, the Biginelli reaction furnishes a very easy approach to the synthesis of a library of biological active compounds in an academic course. Here we describe the realization of several experiments…