Paal--Knorr reactions are a classical method for synthesizing pyrroles, using 1,4-dicarbonyl compound and amine as reactants. It has the characteristics of green chemistry, as only two molecules of water are lost. In this teaching and learning experiment, 2,5-hexanedione and 4-"tert"-butylaniline were used to synthesize…

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 urea cycle disorder drug glycerol phenylbutyrate (Ravicti) is presently one of the most expensive medications in the United States, with annual costs estimated at $800,000 as of 2023. An expedient synthesis of this orphan drug was successfully adapted for the undergraduate organic chemistry laboratory. Activation of 4-phenylbutyric acid with…

In this second-semester organic chemistry lab experiment, students work collaboratively using a combination of chemical synthesis and NMR spectroscopy to investigate the diastereoselectivity associated with the Meerwein-Ponndorf-Verley (MPV) reduction of two ketone substrates having carbonyl groups flanked by an [alpha]-chiral carbon with…

Herein, we present an integrated upper division chemistry laboratory experiment involving the synthesis, characterization, and evaluation of catalytic metal--organic frameworks (MOFs). Experiments are designed to facilitate the solvothermal synthesis and characterize MOFs, including UiO-66, UiO-66-NH[subscript 2], and UiO-66-NO[subscript 2]. The…

Normal phase thin layer chromatography is a widely taught technique in undergraduate organic chemistry laboratory courses. To understand how the technique works, students must have a strong conceptual understanding of polarity and intermolecular forces. Unfortunately, many students have misconceptions regarding how polarity and intermolecular…

A comprehensive teaching experiment plan tailored forthird-yearundergraduates has been developed. Initially, instructors synthesize(E)-2-(4-((4-(2-hydroxyethoxy)-3-methylphenyl)­diazenyl)­phenoxy)-ethan-1-ol­(M-Azo-2)monomer as part of the preclass preparation. Subsequently, studentsperform an acylation reaction experiment to prepare an…

Resonance is a crucial concept in Organic Chemistry that enables both deriving chemical properties from molecular structures and predicting reactions by considering electron density distribution. Despite its importance for problem-solving and learning success, learners encounter various difficulties with this concept. Although prior research…

The Brønsted-Lowry acid-base model is fundamental when discussing acid and base strength in organic chemistry as many of the reactions include a competing proton transfer reaction. This model requires evaluating chemical stability "via" a consideration of electronic granularity. The purpose of this study is to identify students' mental…

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.…

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…

An undergraduate laboratory experiment has been developed for the synthesis of a reactive cross-linker that is useful in various highly visual demonstrations of organic reactivity, click chemistry, and biobased polymer synthesis. A triazolinedione-based cross-linker, which is known as a useful reagent for click chemistry, can be obtained from…

An efficient synthesis of the exorbitantly priced Lambert-Eaton myasthenic syndrome drug amifampridine was developed and applied in the second-semester undergraduate organic chemistry laboratory. The two-step synthesis entails a nucleophilic aromatic substitution reaction of commercial 4-chloro-3-nitropyridine with methanolic ammonia to afford…

A one-pot multicomponent synthesis of unsymmetrical indole-substituted methane derivative based on two consecutive reactions of p-methylbenzaldehyde with N-methylindole and 5,5-dimethyl-1,3-cyclohexanedione is described as an experiment that was carried out by second-year undergraduate chemistry students individually in a laboratory classroom. The…

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…