Abstract
This chapter covers a series of laboratory experiments developed to provide a practical integration of green and sustainable chemistry concepts into the secondyear organic chemistry laboratory. The chapter also offers an example of a successful undergraduate research project in chemistry that demonstrates how a green chemistry project can make research-based learning feasible even in institutions with limited resources. The five laboratory experiments are based on a single, secondary plant metabolite, cinnamaldehyde, and the sixth experiment revisiting the tie-dyeing processe through a bioinspired and safer alternative to nucleophilic aromatic substitution (SNAr) reactions. Cinnamon oil was obtained through hydrodistillation, and cinnamaldehyde was used to carry out a reduction reaction, an aldol reaction, and the Schiff base formation. Students can practice techniques such as thin-layer chromatography, column chromatography, recrystallization, and melting point along with UV, Fourier-transform infrared, and 1H-nuclear magnetic resonance spectroscopies through these experiments. Microscale practices were employed in each of the reactions, and microscale column chromatography was used for purifications. The fifth experiment was an antimicrobial activity assessment of cinnamon oil and the cinnamaldehyde derivatives obtained from the previous experiments. Along with an interdisciplinary component, students were exposed to sunscreen chemistry and were led to consider the many uses of each product obtained. In the sixth experiment (tie-dyeing experiment), the water-soluble reactive dye that replaces 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. The undergraduate research project focuses on developing a bioinspired, environmentally friendly wound-care product derived from chitosan and two naturally occurring aldehydes, citronellal and cinnamaldehyde. In this project, the student researcher prepared two chitosan Schiff bases using citronellal and cinnamaldehyde and then characterized and evaluated these products’ antimicrobial properties.
