NMR Studies of Structure–Reactivity Relationships in Carbonyl Reduction: A Collaborative Advanced Laboratory Experiment

Abstract

An upper-division laboratory project has been developed as a collaborative investigation of a reaction routinely taught in organic chemistry courses: the reduction of carbonyl compounds by borohydride reagents. Determination of several trends regarding structure−activity relationship was possible because each student contributed his or her results to an overall data set in a situation similar to a research environment. The students learned to use 1 H NMR techniques for in situ kinetic determinations and collaborated with classmates to develop a complete theory for structure−activity effects in the kinetics of this fundamental organic reaction.

10 Guiding principles for learning in the laboratory

“…Encouraging students to be aware of variance in methods and results has a potential for developing a critical mindset regarding experimental data (Agustian et al, 2022b). Examples from the literature include experiments in organic synthesis (Santos Santos et al, 2010) and spectroscopy (Marincean et al, 2012), demonstrating the utility of this approach in more challenging laboratory contexts. MacKay and Wetzel (2014) provide extensive detail on this approach in an experiment where different students in the cohort are tasked with exploring different aspects that may affect the Wittig reaction, with students required to make a hypothesis about their choice of reagent (from an approved list) and conduct an experiment to test that hypothesis.…”

Incorporating Interlab Collaborations into the Organic Chemistry Teaching Laboratories

“…Models of collaborative classroom and laboratory experiences, including potential benefits, have been extensively explored and cited in the literature; ,, therefore, this topic will only be discussed briefly. Examples of group work in general chemistry, − organic chemistry, − and advanced chemistry laboratories − have been reported. Traditionally, students from the same lab section (and course) work together, although collaborations across courses have also been reported. − For example, to model drug discovery, students in organic and biochemistry courses synthesized an antibiotic and tested its biological properties .…”

Synthesis of 1-Phenylthiourea: An Undergraduate Organic Chemistry Experiment Illustrating Carbonyl Transformations

“…The chemistry of carbonyl compounds is a fundamental part of undergraduate experiments and has been outlined in many undergraduate textbooks. , Undergraduate students are routinely exposed to many experiments involving the chemistry of carbonyl-containing structures. These include carbonyl condensation reactions, carbonyl reactions in multistep syntheses, microwave-assisted synthesis of carbonyl compounds, carbonyl addition reactions and their stereochemistry and regiochemistry, and NMR and FT-IR spectroscopic studies. However, few of the experiments deal with reactions of carbonyl substitution and concomitant addition in a simple and applicable synthetic way.…”