A Green Nucleophilic Aromatic Substitution Reaction

Abstract

This paper revisits the tie-dyeing process through a bioinspired and safer alternative to nucleophilic aromatic substitution (SNAr) reactions for an introductory organic chemistry laboratory. The simple and straightforward experiment provides students with an opportunity to gain practical experience in conducting a chemical reaction in a real-world context while applying concepts of design for biodegradability and reusability. The water-soluble reactive dye that replaces the use of a conventional SNAr substrate does not require any heavy metals, toxic substances, or mordants but utilizes a much less toxic and safer sodium carbonate to generate the cellulosate nucleophile. This reaction generates no waste, and the end-product, the tie-dyed T-shirt, is reusable and biodegradable. Through this experiment, students can see connections between chemistry and environmental health while gaining a practical insight into dyeing chemistry, making use of a systems thinking approach. This experiment serves not only to employ safer alternatives to hazardous chemicals in the undergraduate organic chemistry laboratory but also to educate students to recognize the relevance and importance of applying green chemistry wherever it is possible, emphasizing life cycle thinking and stewardship.

Creativity of Nanofiber Materials and Application in the Expressive Power of Manual Tie-Dyeing Process

“…is reaction produces no waste and the final product -the tie-dyed t-shirt is reusable and biodegradable. rough this experiment, students can see the link between chemistry and environmental health while gaining a practical understanding of dye chemistry using systems thinking approach, but its practicality is not strong [1]. Yang et al researched and reproduced a Northern Dynasty tie-dyed female silk garment from the China National Silk Museum.…”

A Green and Efficient Cyclization of Citronellal into Isopulegol: A Guided-Inquiry Organic Chemistry Laboratory Experiment

“…Increasingly, instructors, departments, and universities are acknowledging the need for sustainable practices in chemistry, and it is becoming more common to incorporate green chemistry into laboratory education. − Green chemistry education has many benefits, including increased safety and the practical incorporation of environmentally sustainable practices into student activities. As it reduces both the hazards and the costs of laboratory exercises, it is ideal for any university, including small universities limited in funding and equipment …”

“…These experiments allow students to achieve the foundational learning outcomes for organic chemistry while gaining practical experience with green and sustainable chemistry concepts. Ambrose has also developed a bioinspired and safer alternative to nucleophilic aromatic substitution (S N Ar) reactions, based on the real-world technique of tie-dyeing, which employs 9 of the 12 green chemistry principles . Most of these green chemistry experiments were developed through undergraduate research projects …”

“…The chemistry curriculum at Ambrose is dedicated to incorporating green chemistry into lecture and laboratory material. Organic Chemistry II is a second-year course for students enrolled in the B.Sc Biology program. , …”

“…Ambrose has also developed a bioinspired and safer alternative to nucleophilic aromatic substitution (S N Ar) reactions, based on the real-world technique of tie-dyeing, which employs 9 of the 12 green chemistry principles. 4 Most of these green chemistry experiments were developed through undergraduate research projects. 5 To add to our repertoire of green chemistry laboratory experiments, we decided to investigate the cyclization of citronellal to isopulegol:…”