Designing a Green, Multistep Synthesis with an Intramolecular Diels-Alder Reaction for the Undergraduate Teaching Laboratory
Disciplines
Organic Chemistry
Abstract (300 words maximum)
Multistep synthesis is a key learning objective for the undergraduate organic chemistry teaching laboratory. Yet, there is a notable gap in chemical education literature where multistep synthesis laboratory modules are embedded with green chemistry principles. The objective of this research endeavor is to develop a novel, multistep synthesis laboratory module that includes previously unexplored intramolecular Diels-Alder reactions. Our three-step synthesis utilizes bio-sourceable reagents—vanillin, furfurylamine, maleic anhydride—where each step is conducted under mild reaction conditions to enhance energy efficiency and minimize waste. The final product generated via an intramolecular Diels-Alder reaction reveals an unusual stereochemical outcome. This multistep synthesis confers high pedagogical value—allowing students to explore a stereospecific, intramolecular cycloaddition where each step is evaluated against the 12 Principles of Green Chemistry. In conclusion, this laboratory module offers a scalable model for sustainable synthetic practices in the undergraduate organic chemistry teaching laboratory.
Use of AI Disclaimer
no
Academic department under which the project should be listed
CSM – Chemistry and Biochemistry
Primary Investigator (PI) Name
Animesh Aditya
Designing a Green, Multistep Synthesis with an Intramolecular Diels-Alder Reaction for the Undergraduate Teaching Laboratory
Multistep synthesis is a key learning objective for the undergraduate organic chemistry teaching laboratory. Yet, there is a notable gap in chemical education literature where multistep synthesis laboratory modules are embedded with green chemistry principles. The objective of this research endeavor is to develop a novel, multistep synthesis laboratory module that includes previously unexplored intramolecular Diels-Alder reactions. Our three-step synthesis utilizes bio-sourceable reagents—vanillin, furfurylamine, maleic anhydride—where each step is conducted under mild reaction conditions to enhance energy efficiency and minimize waste. The final product generated via an intramolecular Diels-Alder reaction reveals an unusual stereochemical outcome. This multistep synthesis confers high pedagogical value—allowing students to explore a stereospecific, intramolecular cycloaddition where each step is evaluated against the 12 Principles of Green Chemistry. In conclusion, this laboratory module offers a scalable model for sustainable synthetic practices in the undergraduate organic chemistry teaching laboratory.