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Solvent Selection for SN1 and SN2 Reactions in Green and Sustainable Chemistry

Solvent Selection for SN1 and SN2 Reactions in Green and Sustainable Chemistry
Contributors
Portfolio Manager for Education ACSGCI | American Chemical Society Green Chemistry Institute (ACS GCI)
Associate Professor | Radford University
Learning Objets
Summary
This module explores nucleophilic substitution reactions and how solvent selection correlates to reaction mechanisms for SN1 and SN2 reactions (i.e., reaction product, selectivity, and stereochemistry). Solvents are discussed with respect to environmental, health, safety, and life-cycle considerations. This module can be used when nucleophilic substitution reactions are introduced and is designed to replace approximately one week of class material. This module expands the typical SN1/SN2 discussion of solvents to include a systems thinking approach and interdisciplinary applications. Solvent choice relates directly to UN SDG 12: Responsible Consumption and Production and Green Chemistry principles 5 (safer solvents and auxiliaries), 1 (waste prevention), and 7 (renewable feedstocks).

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 Teresa Fernando and Sarah A. Cummings 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.
Learning Goals/Student Objectives
A. Identify a chemical reaction as SN2 and predict products, using arrow-pushing mechanisms, and applying chemo- and stereoselectivity concepts.
B. Use molecular properties such as dielectric constant, H-bonding ability, boiling point to select solvent for SN2 reaction.
C. Use systems thinking to analyze sustainability issues in choice of solvent for an SN2 reaction.
D. Identify a chemical reaction as SN1 and predict products, using arrow-pushing mechanisms, and applying chemo- and stereoselectivity concepts.
E. Use molecular properties such as dielectric constant, H-bonding ability, boiling point to select solvent for SN1 reaction.
F. Use systems thinking to analyze sustainability issues in choice of solvent for an SN1 reaction.
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
Common pedagogies covered
Collaborative/cooperative learning
Problem-based learning
Student-centered learning
Technology-enhanced learning
Green Chemistry Principles
Waste Prevention
Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
U.N. Sustainable Development Goals (SDGs)
Responsible Consumption and Production
Safety Precautions, Hazards, and Risk Assessment
N/A

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