Abstract

           Electrophilic aromatic substitution reactions are important in organic chemistry because they are a way elemental groups can be added onto very stable molecules.  The ortho effect is a phenomenon which exists during an electrophilic aromatic substitution reaction of a benzene ring that contains both an ortho/para-director and a meta-director situated meta to the ortho/para-director.  The research reported here investigates the effect resonance has on the ortho effect.  This was investigated with the nitration reaction of 3-chlorobenzotrifluoride.  The product mixture was analyzed with the use of thin layer chromatography, proton nuclear magnetic resonance spectroscopy, and flash column chromatography.  Each of these analysis methods allows for determination of the number of different isomers present in the product mixture, relative amounts of each, and to help correctly identify each isomer.  After analyzing the crude product mixture, evidence of three isomers were present.  This finding goes against the ortho effect and suggests there is a possible link between the ortho effect and resonance of substituents. For future studies, the findings of this research could possibly allow for greater investigations into new synthesis methods of notorious stable molecules.