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Carbonyls Redox: Aldehydes and Ketones

Carbonyls Redox: Aldehydes and Ketones
Contributors
Professor Emerita
Virginia Polytechnic Institute and State University
Portfolio Manager for Education ACSGCI | American Chemical Society Green Chemistry Institute (ACS GCI)
Associate Professor | Radford University
Learning Objets
Summary
This module covers aldehydes and ketones as the substrates and products of redox reactions. Structure is explained with both Lewis structures and molecular orbitals to discuss mechanisms in the context of green chemistry. Students need to be familiar with organic functional groups, reactions, and proposing a mechanism.

The goal of this module is to understand the structure, reactions, and uses of aldehydes and ketones. Conventional redox reactions as a class comprise some of the most wasteful and toxic reactions, and greener redox reactions are an opportunity to update the curriculum with more sustainable chemistry. Students will use mechanism-based understanding of nucleophiles and electrophiles to choose greener reaction conditions for redox reactions of aldehydes and ketones as starting materials (including some as biofeedstocks), or products of alcohol oxidation. Students will evaluate and develop a Systems Oriented Concept Map Extension (SOCME) to compare and evaluate the environmental impact, toxicity, and life cycle from source to the end-fate of retinoids in skin treatments.

There are four units: 1.) nomenclature, structure, and oxidation state, 2.) reduction of aldehydes and ketones, 3.) carbon-carbon bond forming reactions of carbonyls, 4.) oxidation to make aldehydes and ketones, and retrosynthetic analysis. Unit 1 also serves as a platform to introduce and reinforce the concepts of systems thinking using a Systems Oriented Concept Map Extension (SOCME) assignment.

Green chemistry concepts include: 1.) using biofeedstocks for oxidation-state matching to improve multi-step synthesis, 2.) synthetic efficiency, 3.) preventing waste through reagent selectivity and balanced reactions, 4.) avoiding the toxicity and hazards of reagents and by-products, and 5.) chemical and enzymatic redox catalysis. UN SDGs 3: Good Health, 8: Safe Working Environment, 10: Reduced Inequalities, 12: Responsible Consumption and Production, and 13: Climate Action are addressed in this module.

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 Felicia A. Etzkorn, Jamie L. Ferguson, and Maggie B. Bump 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. Understand the structure, properties, and reactivity of aldehydes and ketones.
2. Recognize that reactants are available in a variety of oxidation states for the same carbon core structure.
3. Choose a biofeedstock that is close to the oxidation state of the desired product for fewer steps.
4. Determine whether a reduction or oxidation has occurred, based on the structure of organic reactants and products.
5. Predict the reactant, reagent, product, and by-products of a carbonyl reaction.
6. Recognize the parallels between chemical and biochemical reagents.
7. Evaluate the sustainability of reducing and oxidizing reagents based on source, by-product waste, hazards, and suitability for the desired reaction.
8. Propose the mechanism of a carbonyl reaction.
9. Design a synthesis by retrosynthetic analysis that uses redox and carbon-carbon bond-forming reactions of carbonyl compounds.
Object Type
Lecture or course slides/notes (e.g., PPT, Prezi, PDF)
Lesson summaries
Exam questions and answers
Assessments
Small resource sets
Audience
Introductory Undergraduate
Upper/Advanced Undergraduate
Common pedagogies covered
Context-based learning
Problem-based learning
Green Chemistry Principles
Waste Prevention
Less Hazardous Chemical Syntheses
Designing Safer Chemicals
Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Catalysis
Safer Chemistry for Accident Prevention
U.N. Sustainable Development Goals (SDGs)
Good Health and Well-Being
Decent Work and Economic Growth
Reduced Inequalities
Responsible Consumption and Production
Climate Action
Safety Precautions, Hazards, and Risk Assessment
N/A
Teacher Recommendations or Piloting Data (if available)
Instructor notes are in a document within the downloadable zip file.
NGSS Standards, if applicable
N/A

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