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Stereochemistry: Introduction to Chirality

Stereochemistry: Introduction to Chirality
Contributors
Teaching Professor | Xavier University
Lecturer | Loyola University Chicago
Associate Professor of Instruction | Ohio University
Portfolio Manager for Education ACSGCI | American Chemical Society Green Chemistry Institute (ACS GCI)
Associate Professor | Radford University
Learning Objets
Summary
This module has been designed to introduce second-year organic chemistry students to the concepts of stereochemistry through the lens of the World Health Organization’s Model List of Essential Medicines. PowerPoint slide decks, homework assignments, instructor notes, activities, and a summative assessment are included in this module. Students should be able to represent and classify stereoisomeric relationships and evaluate the implications of synthesizing small molecules for use as chiral drugs.

Chirality is discussed, followed by enantiomers, diastereomers, racemic mixtures, and meso compounds. Optical activity and Fischer projections are also covered. These topics span a timeframe of approximately four 50-minute class periods. This module connects to the UN SDGs of Good Health and Well-being, Gender Equality, Reduced Inequalities, and Responsible Production and Consumption.

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 Kendra Denlinger, Rebecca Haley and Heather Hopgood 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
Students will be able to:
1. Define chirality and identify stereocenters in organic compounds, including pharmaceutical drugs.
2. Draw the possible stereoisomers of various molecules.
3. Distinguish between enantiomers, diastereomers, and meso compounds and explain their physical properties, especially in chiral environments such as the human body.
4. Use the Cahn-Ingold-Prelog convention to correctly assign R and S nomenclature
5. Define racemic mixture and determine the enantiomeric excess of a mixture.
6. Explain some implications of stereoisomerism with respect to health and well being.
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
Context-based learning
Problem-based learning
Green Chemistry Principles
Designing Safer Chemicals
Reduce Derivatives
U.N. Sustainable Development Goals (SDGs)
Good Health and Well-Being
Gender Equality
Reduced Inequalities
Responsible Consumption and Production
Safety Precautions, Hazards, and Risk Assessment
N/A
Teacher Recommendations or Piloting Data (if available)
See the "Learning environment and context" section of the Module Overview document in the downloaded files for piloting data.

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