With applications in areas ranging from biological systems to food chemistry and polymers, esters are foundational motifs readily synthesizable using acyl substitution reactions. As such, ester formation is a common component of most undergraduate laboratory courses but is often limited in scope and impact during the laboratory experiment. In an effort to develop an inquiry-based lab around esterification, a scope study prepared twenty unique p-nitrobenzoate esters under optimized, solvent-free conditions. The products were analyzed using NMR and IR spectroscopy as well as GC-MS and melting point. Moreover, the influence of sterics on reaction rates were quantified through competition studies. Combined, the results provide an ideal avenue to explore foundational organic principles in an undergraduate laboratory setting.

Synthesis of a library of p-nitrobenzoate esters and the influence of sterics

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.