Advanced Organic Chemistry

This module is part of a collection of nine green chemistry teaching modules developed in the early 2000s by a team of faculty (Donna Narsavage-Heald, Trudy Dickneider, David Marx, Timothy Foley, Joan Wasilewski) led by Michael Cann at the University of Scranton and has been migrated to the GCTLC. The subjects of the modules are based on winners of the Green Chemistry Challenge Awards. The modules were used to infuse green chemistry across the curriculum (courses: general chemistry, organic, advanced organic, biochemistry, environmental, industrial, polymer, inorganic, toxicology). Infusion of green chemistry across the curriculum provides students the understanding that green chemistry is not a field unto itself but impacts all areas of chemistry. Having been exposed to many green chemistry examples students are likely to think green in their ensuing careers. The resources are provided as is in their original form, for reference and archival purposes. Therefore, some of the material may no longer be current, and some links may no longer be active. An interesting project would be to update the material in this module.

The advanced organic chemistry module introduces the traditional method for producing 4-aminodiphenylamine (4-ADPA), an intermediate compound used in the rubber industry, and highlights its environmental drawbacks. It discusses the mechanism of nucleophilic aromatic substitution (NAS) reactions, focusing on the SNAr and Benzyne mechanisms. The traditional method involves multiple electrophilic aromatic substitution (EAS) reactions, leading to poor atom economy and environmental concerns such as chlorine usage and waste generation.

The module then introduces an alternative green chemistry approach developed by Flexsys America, which utilizes nucleophilic aromatic substitution for hydrogen (NASH) reactions to eliminate the need for chlorinated starting materials. This new method significantly reduces organic and inorganic waste, eliminates the use of chlorine and xylene, and improves industrial safety. The Flexsys NASH reaction demonstrates a higher atom economy compared to the traditional method.

Major funding for this project came from The Camille and Henry Dreyfus Foundation Special Grant Program in the Chemical Sciences. The ACS/EPA Green Chemistry Educational Materials Development Project and the University of Scranton provided additional funding.

This module is also available in Spanish and Portuguese versions.