A deep understanding of organic chemistry requires a learner to understand many concepts and have fluency with multiple skills. This understanding is particularly necessary for constructing and using mechanisms to explain chemical reactions. Electrophilicity and nucleophilicity are two fundamental concepts to learning and understanding reaction…

Organic reaction mechanisms lie at the heart of developing an understanding of how the molecular world functions. However, many students simply try to memorize mechanisms, or use their knowledge of the reagent and product to create a mechanism that "works". This is not helped by the content-heavy organic chemistry curriculum which…

A straightforward protocol for the preparation of the colorful and air-stable diphenyl ditelluride is described. In one laboratory session, students isolate their product and characterize it via melting point determination, mass spectrometry, and NMR spectroscopy ([superscript 1]H, [superscript 13]C­{[superscript 1]H}, and [superscript…

Understanding organic reaction mechanisms can be a challenging task for many undergraduate students, particularly those who are nonchemistry majors, despite the fact that organic chemistry is a mandatory course for numerous science and engineering undergraduate programs. The selectivity of a reaction is largely determined by the distribution and…

This review describes a computational chemistry exercise aimed at enhancing the understanding of upper-division undergraduates in organic chemistry and physical chemistry regarding the structures and aromaticities of cyclobutadiene and cyclooctatetraene. This exercise exposes students to chemical problems that require computational methods as a…

Chemistry undergraduate curricula typically place Nuclear Magnetic Resonance (NMR) lectures under either Organic Chemistry or Spectroscopy courses, aiming for students to acquire basic knowledge for the determination of the structure of simple organic compounds. On the other hand, regarding laboratory practice, NMR is frequently disregarded by…

Infrared spectroscopy (IR) is a staple structural elucidation and characterization technique because of its ability to identify functional groups and its ease of use. Interestingly, it allows the capture of electronic effects via their influence on the bond strength of "probes", such as the carbonyl group and also offers a wealth of…

The Databank of Dynamics Trajectories (DDT, notthatddt.org) was established to assist students in visualizing the dynamical behaviors occurring during chemical reactions and conformational changes, with a focus on processes taught in introductory organic chemistry classes. Animations of reacting molecules created using "ab initio"…

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…

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,…

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…

The inductive effect is one of the very important concepts of electronic effects in organic chemistry. In traditional teaching methods, only the origin, transmission mode, and decay of the inductive effect are introduced briefly, which is not conducive to students' complete understanding of the inductive effect. This work developed a new method to…

A structured series of activities has been designed and implemented to promote analysis and data reporting skills for second-year organic chemistry students. Student report sheets were developed to assist students in reporting necessary data for their compounds. A series of rubrics have been utilized by students to promote metacognition and by…

Different molecular representations are usually used to depict the three-dimensional (3D) structure of organic compounds. Mastering the skill of interconverting one form into another is essential for students to ensure success in organic chemistry. The traditional and recently developed methods for completing such interconversions that rely on 3D…

This paper describes the design and evaluation of the Organic chemistry Representational Competence Assessment (ORCA). Grounded in Kozma and Russell's representational competence framework, the ORCA measures the learner's ability to "interpret," "translate," and "use" six commonly used representations of molecular…