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Pericyclic Reactions

Pericyclic Reactions
Contributors
Yalan Xing
Associate Professor | Hofstra University
David Laviska
Portfolio Manager for Education ACSGCI | American Chemical Society Green Chemistry Institute (ACS GCI)
Sarah Kennedy
Associate Professor | Radford University
Learning Objets
Summary
This module teaches fundamentals of pericyclic reactions using examples of biocatalysis, biomimetic catalysis, and natural product total synthesis. After completion, students should be able to identify key disconnections of pericyclic reactions (specifically [4+2] and [2+2] cycloadditions, as well as [3,3]-sigmatropic rearrangements) for the preparation of agrochemicals and natural products (SDG 2: Zero Hunger) and pharmaceuticals (SDG 3: Good Health and Well-Being).

The goals of this module are for students to
-be able to identify key disconnections for pericyclic reactions, as well as compare and contrast synthetic routes involving pericyclic reactions.
-be able to apply pericyclic reactions in understanding the synthesis of pharmaceuticals and agrochemicals.
-analyze the role of biomolecules and supramolecules as catalysts for pericyclic reactions, and explore the role of pericyclic reactions in biogenesis of complex molecules.

The module contains lecture slides, group discussions, practice problems, in-class activities, and a summative assessment.

The GCTLC learning object external link takes you to the ACS GCI website to download the learning materials. Once there, use the Module Overview document to guide you through using these impactful learning materials.

This module was developed by Yalan Xing and Michael C. Young for the green chemistry educational module project with the American Chemical Society Green Chemistry Institute; Sarah Kennedy and David Laviska reviewed and published the module.
Keyword Tags
Pericyclic
Organic Chemistry
Biocatalysis
Systems Thinking
Green Chemistry Metrics
Society and Ethics
Catalysis
Link to external
Link to ACS GCI module page
Learning Goals/Student Objectives
Students will be able to:

1. Identify disconnections for pericyclic reactions, including the Diels-Alder and [3,3]-sigmatropic rearrangements, as well as explain and apply the mechanisms of different pericyclic reactions and derive the reaction products based on provided starting materials and reaction conditions.
2. Recognize the reaction conditions required for different pericyclic reactions, including thermal, catalytic (Lewis acid catalysis and biocatalysis), and photo conditions, as well as identify green reaction conditions based on green chemistry principles.
3. Identify cyclic fragments that can be synthesized by pericyclic reactions in complex bio-active molecules
4. Compare the sustainability of pericyclic reactions with regard to atom economy and process mass intensity.
5. Describe the advantages and disadvantages of different types of catalysis (Lewis acid, Biocatalytic, “On-Water”) on the sustainability of pericyclic reaction strategies in complex molecule synthesis.
6. Discuss the societal benefits and drawbacks of applying pericyclic reactions to human well-being through SDG 2 and SDG 3.
Object Type
Lecture or course slides/notes (e.g., PPT, Prezi, PDF)
Activities/Technology (e.g., in-class activities, online games, hands-on activities/manipulatives, outreach, virtual tools, etc.)
Assessments
Small resource sets
Audience
Introductory Undergraduate
Upper/Advanced Undergraduate
Other Faculty Educators/Teachers
Common pedagogies covered
Collaborative/cooperative learning
Problem-based learning
Student-centered learning
Green Chemistry Principles
Waste Prevention
Atom Economy
Design for Energy Efficiency
Catalysis
U.N. Sustainable Development Goals (SDGs)
Zero Hunger
Good Health and Well-Being
Safety Precautions, Hazards, and Risk Assessment
N/A
Teacher Recommendations or Piloting Data (if available)
Module was taught at The University of Toledo to ~100 student lecture of 50 minutes or to ~60 students in a lecture of 80 minutes. Because we use Vollhardt and Schore, Activity 1 was placed in Organic I while Activity 2 was used in Organic 2. Based on allotted class time, the Summative Assessment were found to be easier to budget time for by placing into online discussion boards that were already planned for other systems thinking activities. The module was also taught at Hofstra University to approximately 50 students in an 80-minute lecture and at William Paterson University to around 30 students in a 50-minute lecture. The summative assessments were conducted as homework assignments. The activities served as excellent exercises during the active learning sections.

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Submitted by

Sarah Kennedy
Published on
Moderation state
Published
Collection
ACS Green Chemistry Teaching Modules