In addition to illustrating the archetypal nucleophilic acyl substitution reaction, the formation of p-nitrobenzoate esters from the reaction of a diverse range of alcohols and p-nitrobenzoyl chloride was developed to highlight the role of electronics and sterics on reactivity. Over thirty different esters including a range of secondary functional groups and diester products were prepared. The results provide sufficient diversity to give each student in a given section a unique experience. Optimization of the reaction resulted in high yields, short reaction times (less than 30 minutes) and typically solvent-free conditions. Moreover, competition studies with p-phenols delineated the role of electronics while varying substitution of alkyl derivatives enabled the facile evaluation of steric effects on reaction rates. The results are ideally suited to an inquiry-based lab either in one session or spread across multiple meetings and suggestions for implementation will also be discussed.

Synthesis of p-nitrobenzoate esters to illustrate roles of sterics and electronics in an undergraduate organic laboratory

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.