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…

A renewed experimental procedure for the unknown carbonyl experiment has been developed using hydrazone synthesis, thin layer chromatography (TLC) analysis, and melting point determination to differentiate between structurally similar ketones and aldehydes in undergraduate organic chemistry practical courses. Benzaldehyde, p-tolualdehyde,…

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…

Solving problems in organic chemistry often requires the consideration of reaction mechanisms. As such, much research has been devoted to the examination of how students consider mechanisms when solving various types of organic chemistry problems, such as predicting the products of a reaction or proposing a synthesis. This article provides a…

A multicomponent reaction was adapted and successfully applied in the major organic course, which involves synthesizing and characterizing a 1,3-benzoxazine derived from paracetamol extracted from tablets of the worldwide well-known medicine Tylenol. Using paracetamol as a reagent is a motivational strategy in undergraduate laboratories to meet…

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.…

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…

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…

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…

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,…

As a model study for improving undergraduate organic chemistry laboratories with contemporary research concepts and practices, we evaluated a project module aiming at the synthesis of two porphyrin compounds. The module was implemented in a format that differed in several ways from that of a traditional course. It was designed for small student…

We describe a three-day advanced organic laboratory experience that includes the solid-phase synthesis of an unknown three amino acid polypeptide for junior/senior undergraduate chemistry majors. Students conduct a series of 1D and 2D NMR experiments (HSQC, HMBC, TOCSY) and analyze the data to identify the side chain residues of the peptide and…

In this in-class activity, organic chemistry undergraduates try to place an assortment of molecules in chronological order from oldest to most recently synthesized. In the students' first attempt, they use their knowledge of reactions and synthesis to analyze the organic compounds for their structural complexity. Before a second attempt, the names…

In this laboratory teaching experiment, commercial cannabis oils were analyzed by undergraduate organic chemistry students using gas chromatography-mass spectrometry (GC-MS) to investigate three isomeric cannabinoids commonly found in cannabis products: cannabidiol (CBD), [delta][superscript 9]-tetrahydrocannabinol ([delta][superscript 9]-THC),…