Recent advances in laboratory automation and digitization require a teaching strategy for undergraduate students that is inclusive of skills in these areas so that students can be prepared to work within the modern laboratory. Future scientists will need training in coding, microcontrollers, on-demand manufacturing, and robotics. With this in…

An undergraduate laboratory experiment for the synthesis of biologically significant bis-4-hydroxycoumarins using a new catalyst is described here. An experimental setup plan, monitoring the reaction by TLC, isolation of the product, safe laboratory handling procedures, and significance of data reproducibility of the result are the main learning…

Amides are usually prepared using amines and acyl halides, which often implies a two-step procedure. Alternatively, coupling reagents can be used in a single-step reaction with good yields, which seems to be suitable for organic chemistry laboratory classes. This work was designed to synthesize "N"-hexylcinnamamide through a one-step…

A pedagogically useful undergraduate organic-chemistry-laboratory experiment has been developed that involves the synthesis of two structurally simple, achiral "O,O"- and "N,N"-acetal substrates with no stereocenters. The experiment introduces students to a "new" and more effective variant of classical acetal…

The Clemmensen reduction is a common example of a reaction demonstrating the deoxygenation of carbonyl groups, which is a topic that has been widely studied in the field of organic chemistry. The use of trimethylchlorosilane, as a substitute for concentrated hydrochloric acid, allows for the reduction of carbonyl groups. The Clemmensen reduction…

In response to the call for an increased emphasis from the American Chemical Society on including macromolecular studies in the undergraduate curriculum, a supramolecular-themed experiment was designed for undergraduate-level organic laboratory courses that provides a convenient platform to study physical behaviors of supramolecular assemblies.…

A laboratory exercise for the synthesis of a sulfonated styrene-"co"-maleic anhydride polymer and its application as a stain blocker on nylon-6,10, is described. The effectiveness of the sulfonated polymer to prevent the conjugate base of an acid dye from staining the polyamide is demonstrated. This experiment is designed for…

"N"-Formamides are important intermediates in the synthesis of many pharmacologically active compounds and are used as protecting groups for amines or as catalysts in different reactions. The current "N"-formylation experiment is designed as a part of an introductory organic chemistry course for undergraduate students. The…

The chemistry of metal-organic frameworks (MOFs), a new class of emerging crystalline porous solids with three-dimensional (3D) networks composed of metals and multidentate organic molecules, was introduced by using three differently shaped crystals. We reported new and mild MOF synthesis methods that are simple and devised to be performed in high…

The free radical chlorination of an alkane experiment is often used in the undergraduate laboratory curriculum to introduce students to the free radical mechanism, substituent effects, intermediate stability, and the relative reactivity of radicals. In this experiment, students monochlorinate multiple alkanes and analyze the reaction mixture using…

A bridge course intended to ease the transition from Organic Chemistry I to II was designed for a January term that spans 2 weeks and features sharply focused topics courses. In the first week, key topics from Organic Chemistry I are revisited to ensure that students have a firm foundation on which to build. During the second week, a selection of…

Keto-enol tautomerism is a special example of structural isomerism. In this experiment, 6-chlorofulvene is predominantly yielded during the chlorination reaction of 6'-hydroxyfulvene with POCl[subscript 3] in the presence of DMF. The high regioselectivity of this reaction is dominated by intramolecular hydrogen-bonding and steric hindrance,…

The VSEPR model has well-established limitations in its ability to represent accurate molecular and electronic geometries of simple molecules, which can create a significant need for students to relearn structure and bonding concepts in organic chemistry. We present an alternate method for describing molecular geometries and electronic structures…

A discovery-based undergraduate organic chemistry lab experiment has been developed in which students establish the diastereoselectivity of hydride reduction of the a-chiral ketone (±)-benzoin isopropyl ether to erythro and threo diastereomeric alcohols by two different reducing agents. Students achieve this goal by working collaboratively and…

Regioselectivity in hetero Diels-Alder reactions can be observed in a simple reaction between a nonsymmetrical heterodiene and an unsymmetrical heterodienophile. A 9 h and easy to implement laboratory experiment is described, in which students can observe the regioselectivity of inverse "electron-demand" hetero Diels-Alder reactions of…