Electrophilic aromatic substitution (EAS) represents an important class of reactions taught in the undergraduate organic curriculum. The reaction of X-substituted benzene derivatives is generally described as proceeding through a carbocation intermediate and the predominant product is ortho/para or meta depending upon the nature of X. Other molecular properties such as molecular orbitals, Hirshfeld charges, C-13 and H-1 NMR shifts can also predict the directing nature of X. Systems ranging from mono-substituted benzenes to di-substituted benzene derivatives and fused rings are presented. <br/>  The goal of this laboratory exercise is to demonstrate the power of computational methods to determine the location of the substitution in EAS reactions by moving beyond molecules in which resonance structures can easily predict the product. This approach also provides molecules in which the computed data does not all agree and students must weigh the data to make an argument about where substitution will occur.<br/>

Utilizing computational chemistry to predict regioselectivity in electrophilic aromatic substitution reactions

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.