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…

Chemical reactions that mimic the function of ATP hydrolysis in biochemistry are of current interest in nonequilibrium systems chemistry. The formation of transient bonds from these reactions can drive molecular machines or generate materials with time-dependent properties. While the behavior of these systems can be complicated, the underlying…

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.…

Nuclear magnetic resonance (NMR) spectroscopy has become a cornerstone tool for studying a variety of molecular features in advanced chemistry laboratories. In this experiment, students prepare a pyrrole-[beta]-amide via a one-pot, three-step synthesis and use NMR spectroscopy to confirm its molecular structure. In addition, variable temperature…

Green chemistry metrics and life-cycle analysis (LCA) were used to assess inefficiencies in two current organic chemistry experiments conducted in third-year organic chemistry to synthesize ("E")-stilbene from benzaldehyde. An alternative Wittig-based, greener, one-pot experiment using the same starting material was selected as a vehicle…

Spectroscopic characterization of molecules is typically reinforced in the organic chemistry teaching laboratory via the analysis of reaction products by NMR and IR, and initial coverage of these topics can include experiments involving the identification of unknown compounds. To combine the unknown identification component with common laboratory…

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…

The acid-catalyzed dehydration of regioisomeric methylcyclohexanols is a classic organic chemistry experiment featured in a variety of laboratory textbooks and literature. The mechanistic details of this reaction have received an inconsistent and occasionally inaccurate treatment, wherein the reaction has been described as a mix of E1, E2-like,…

Polymer chemistry lab experiments present a unique opportunity to allow students to experience the consequences of reaction mechanisms on the properties of the resulting product. In this organic chemistry experiment, students prepared a polyamide by three different reaction mechanisms that represent step-growth and chain-growth methods of…

We herein report an efficient aerobic oxidative cleavage of meso-hydrobenzoin to benzaldehyde using a heterogeneous earth-abundant metal oxide catalyst. The reaction can be carried out at 70 °C in ethanol and uses a balloon filled with O2 as oxidant. Reagents are simple and have long shelf lives, and the whole laboratory exercise can be done in…

Reorienting organic chemistry laboratories with an emphasis on systemic thinking can only be beneficial to students. Addressing the challenges of climate change and the development of renewable resources with a fundamental reaction, such as the hydrogenation of an alkene, will allow students to see organic chemistry as a science beneficial to…

The advanced organic chemistry experiments describe the preparation of fused six-membered lactams to isoxazole and isoxazoline by employing Ugi four-component reaction (U-4CR) and intramolecular nitrile oxide cyclization (INOC) synthetic sequence. The experiments were carried out in 28 h (overnight for U-4CR) and 2 h (for INOC) using commercially…

A four week laboratory experiment was designed on the basis of a modification of the Weiss-Cook reaction for the preparation of "cis"-1,5-dimethylbicyclo[3.3.0]octane-3,7-dione. In general, this very versatile organic reaction involves a two-step process reacting biacetyl with 2 mol of dimethyl-1,3-acetonedicarboxylate to form…

This laboratory experiment visually demonstrates the advanced scientific concept of aggregation-induced emission (AIE) using hands-on learning methods. The experiment is divided into two parts: the first period consists of synthesis and isolation of the organic compound 2(TPA-O)-TPE using typical organic chemistry lab techniques; the second period…

Here we showcase an undergraduate teaching laboratory in which students synthesize and characterize colloidal nanoparticles of organic semiconductors and assess their suitability for applications in printed electronics such as solar cells and bioelectronics. Scanning electron microscopy, UV-visible spectroscopy, and photoluminescence spectroscopy…