Discovery-Based SNAr Experiment in Water Using Micellar Catalysis

Micellar catalysis has become an important aspect of the chemical industry's effort to "go green". However, this chemistry has yet to be fully explored in educational settings such as second-year organic chemistry laboratories. Reported herein is a discovery-based nucleophilic aromatic substitution experiment that introduces chemistry students to micellar catalysis, green chemistry, and systems thinking. The students prepare tandem reactions in water to explore how the leaving group identity affects the rate of reaction and how the reaction incorporates principles of green chemistry. The product of the fastest reaction is isolated through recrystallization, and the product's identity is verified through infrared spectroscopy and melting point analysis.