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…

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,…

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…

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 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 ability to elucidate the structure of organic compounds from their nuclear magnetic resonance (NMR), infrared (IR), and mass spectrometry (MS) spectra is an essential skill, particularly for those engaged in the fields of synthetic and analytical organic chemistry. Spectral analysis constitutes a fundamental component of the curriculum for all…

This communication describes an updated experiment of peptide synthesis, involving determination of the loading capacity of a Fmoc-protected amino functionalized resin using UV-vis spectroscopy and a subsequent synthesis of a dipeptide in order to exemplify the experimental solid-phase synthesis procedure as an alternative technique in organic…

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…

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…

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…

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…

The chemistry of metal-organic frameworks (MOFs) has the potential to introduce high school and undergraduate students to the fundamental chemical principles of structure and bonding, enhance the development of skills in synthesis and crystal growth, and promote hands-on experience with gas capture and host-guest chemistry of emerging materials…

Cycloadditions in combination with multicomponent reactions are among the most valuable synthetic tools used by organic chemists to construct cyclic and heterocyclic compounds in a straightforward way. Although cycloadditions, such as the Diels--Alder reaction, are mainly covered in basic and advanced organic courses for undergraduate students,…

The American Chemical Society advocates a shift from rule-based to risk-based safety education for chemistry graduates, emphasizing meaningful student engagement in the risk assessment process for laboratory work. To implement this paradigm shift, we introduced RAMP (Recognize Hazards, Assess Risk, Minimize Risk, and Prevent Emergencies)-based…

Written examinations for laboratory courses fall short in testing students' technical skills, problem-solving abilities, and execution of experimental design. This has led to practical examinations growing in popularity, but examples for senior-level students remain scarce. Senior organic chemistry students are gearing toward independence to…