In this two-session experiment for an organic chemistry lab, students prepare a macrocyclic host compound--namely, a pillar[5]arene--by means of a templated 1,4-dimethoxybenzene/formaldehyde cyclo-oligomerization (session 1), and then, they explore its molecular recognition properties toward the 1,8-diaminooctane guest with the aid of [superscript…

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…

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…

A new organic chemistry experiment aimed to separate the chlorophyll precursor in plant seeds by column chromatography is described. The primary pedagogical goal in developing this experiment is to establish a simple and interesting chromatographic separation to demonstrate basic concepts and the standard procedure for this important lab…

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 [2 + 2] photocycloaddition reaction of olefins is an effective, atom-economical approach to produce cyclobutane compounds in organic synthetic chemistry, and they usually exhibit high regioselectivity and stereoselectivity. Here we devised a solid-state [2 + 2] photocycloaddition experiment that introduces senior undergraduate students with…

Oxidation reactions are critical components of the synthetic toolbox taught to undergraduate students during introductory organic chemistry courses. However, the oxidation reactions discussed in the undergraduate curriculum are often outdated as many organic chemistry textbooks emphasize chromium-based oxidants that are no longer in regular use by…

Organic chemistry students often struggle with reaction mechanisms, particularly in how they are proposed and justified. In this activity targeting second year organic undergraduates, students used infrared spectroscopy (IR) to track the reaction progress of two distinct aldol reactions and used polarimetry to analyze the stereoselectivity of…

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 new undergraduate organic laboratory experiment has been developed and implemented for the Ugi three-component synthesis of the topical anesthetic lidocaine with excellent atom economy. Paraformaldehyde, diethylamine, and 2,6-dimethylphenyl isocyanide were combined and conveniently stirred at room temperature for a week in methanol with acetic…

A new undergraduate organic laboratory experiment has been developed for amide bond formation between biorenewable 2-furoic acid and either of two substituted piperazines to prepare medicinally relevant amide products using a procedure with industrial significance. The reactions proceeded smoothly under ambient conditions using the combination of…

In an effort to further develop critical thinking and problem solving skills, a guided-inquiry-based, multioutcome organic chemistry synthesis and characterization experiment was developed. Students were provided with the protocol for a time-saving microwave-assisted acetanilide synthesis reaction from acetic anhydride and an unknown primary aryl…

The bromination of six isomeric alcohols is adapted to a discovery-based organic chemistry laboratory experiment, whereby students are provided an alcohol starting material and are charged with determining the product or product mixture produced using relevant spectroscopic data. The experiment solidifies NMR analysis skills while reinforcing the…

This three-part laboratory experiment investigates key aspects of the Buchwald-Hartwig amination cross-coupling reaction through guided-inquiry learning strategies. The first part of this experiment utilizes high-throughput experimentation techniques to reinforce, explore, and extend fundamental concepts that are represented in the classroom,…

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…