The nitration of phenyl benzoate is a simple illustration of the effects of activating and deactivating groups on aromatic rings. The laboratory synthesis involves the electrophilic aromatic substitution reaction of phenyl benzoate with nitric acid to make ortho and para-nitrophenyl benzoate.  As indicated by GC/MS, the crude isomers exhibit essentially identical fragmentation patterns, so fractional crystallization is necessary to obtain pure samples of the regioisomers. Differentiation between isomers is observable via melting point. The relative simplicity of this synthesis makes it possible for an undergraduate organic student to complete within a three-hour lab session. If done in accordance with lecture, the hands on experience might facilitate an organic student's understanding of the fundamental concepts of electrophilic aromatic substitution in addition to demonstrating the use of fractional crystallization to separate regioisomers.

Nitration of phenyl benzoate: Development of an undergraduate organic chemistry laboratory

244th National Meeting (2012)

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