Nitration of substituted benzenes: Recasting an old standby

After participating in the 2006 CWCS workshop Teaching Guided Inquiry Organic Chemistry, I expanded the nitration of methyl benzoate, a popular sophomore organic experiment, to include six other substituted benzenes. Students work in teams, each team nitrating a different compound, and are asked to determine how different substituents will affect the outcome of substitution on the ring. The substitution pattern for each compound is determined by proton NMR. Students pool the data, and use the pooled data to answer the original question. Additionally, a Single Point Energy Calculation was performed using PC Spartan to provide electrostatic potential maps for each compound. This guided inquiry laboratory module combined theory and experiment allowing students to discover substituent effects in electrophilic aromatic substitution.
Authors: 
Jacqueline A Nikles, Dr., PhD
Author Affiliation: 
Department of Chemistry University of Alabama at Birmingham Birmingham Alabama United States