Discovery-Based S_NAr Experiment in Water Using Micellar Catalysis

Abstract

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.

An Organic Chemistry Activity to Improve Student Understanding of Molecules as 3-Dimensional Objects

“…Many of the molecular geometry topics touched on in this activity are topics that the students will learn more about later in the semester, and we believe that it is important to give students the opportunity to discover these ideas as opposed to simply presenting the ideas to them as just more things to memorize. The concept of positioning students to learn through discovery is one that has been highlighted in a number of previously reported organic chemistry lab exercises. − Our work on the DiscoverOChem learning platform , also emphasizes the importance of discovery.…”

A Green Nucleophilic Aromatic Substitution Reaction

“…Several authors have explored the S N Ar reaction while applying a biobased perspective. A discovery-based S N Ar experiment in water was reported to introduce chemistry students to micellar catalysis, green chemistry, and systems thinking . Latimer et al compared microwave-induced organic reaction enhancement to that of more traditional synthetic procedures toward S N Ar reaction .…”

“…A discovery-based S N Ar experiment in water was reported to introduce chemistry students to micellar catalysis, green chemistry, and systems thinking. 38 Latimer et al compared microwave-induced organic reaction enhancement to that of more traditional synthetic procedures toward S N Ar reaction. 39 Rizvi et al determined the activation energy of S N Ar on porphyrins.…”