Aromatic substitution reactions are a commonly discussed topic in an undergraduate organic chemistry class. Although experiments involving electrophilic aromatic substitution reactions are common in the undergraduate organic chemistry laboratory, experiments involving nucleophilic aromatic substitutions are not. We describe a laboratory experiment designed to correlate the rates of nucleophilic aromatic substitution reactions with various aromatic substituents. Students first synthesize O-thiocarbamoyl substrates with a variety of aromatic substituents. Subsequently, the synthesized substrates are used for nucleophilic aromatic substitution reactions and their reaction rates are correlated with their substituents.

Synthesis of o-thiocarbamoyl substrates for application in nucleophilic aromatic aubstitution in the undergraduate organic chemistry laboratory

2019 Spring National Meeting

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