Rick Mullins June 12, 1:00– 4:30 PM, EDT

Organic Education Resources

Making Room for Green Chemistry: Activities

ALOC Online Workshop 2025

June 12, 3:30 – 4:30 PM, EDT

Group Assignment

Aldehydes and Ketones: 1. Create a 10 minute lecture on a green chemistry topic related to your functional group. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your functional group.

Protecting groups - useful but evil??

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Could integrate into a lecture on acetal protection (and they might know TMS by now)

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Show / have them work through an activity to show the utility of protecting groups

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Then, have them do another activity to work through the waste associated with using protecting groups

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Design a synthesis with/without protecting groups (but make it pretty tricky to do without protection OR requires some literature search). Bonus points for non-protection strategy?

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Alternative solvents in context of Grignard chemistry

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Alternative oxidizing agents (as mentioned by Rick and Elsa does a KMnO4 vs. bleach oxidation lab)

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Limiting protecting groups

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Atom economy in the context of synthetic planning

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Temperature

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Varying amounts of solvents needed to clean glassware

10 minute green chemistry lecture

Green chemistry asides

Alkenes: 1. Create a 10 minute lecture on a green chemistry topic related to your functional group. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your functional group.

• Less hazardous synthesis/Prevent Waste:
• Alternatives to KMnO4?
• Anti-Mark HBr addition uses peroxides - safer alternative?
• Don’t want to use oxymercuration because of hazardous chemicals. Come up with alkyl halide starting material that would make two alkenes. Which would you use to be able to apply acid-HBr addition (which involves rearrangements) to avoid needing to use oxymercuration (which avoids rearrangements)?
• Talk about waste protocol for mercury
• Talk through alternative protocols in the lit that are greener ways to do non-arrangement processes (replacing oxymercuration)
• Stoichiometric vs. Catalysis
• Which of these reactions they are learning could be also performed catalytically?
• Highlight some lit papers that could do the same transformations catalytically
• How to calculate Atom Economy,
• Overview, for ozonolysis reaction
• mCPBA (products are solid, fall out of solution)
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10 minute green chemistry lecture

Green chemistry asides

• No one wants to use PCC in the lab (horribly carcinogenic)

Aromatic Substitutions: 1. Create a 10 minute lecture on a green chemistry topic related to your reaction. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your reaction.

Use a historical example of a synthesis that involves aromatic synthesis, e.g. acetaminophen, sulfanilamide. Point out problems with reagents used, feedstocks, etc.

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Show revised synthesis of product. Compare the syntheses and discuss their “greenness” and green chemistry principles that are applied.

Lots of reactions with aromatics are pretty not green!

Friedel-Crafts acylation - using AlCl3 - What alternatives? Good or bad for the environment? - 12 principles address - less hazardous/safety/atom economy

10 minute green chemistry lecture

Green chemistry asides

Carboxylic Acid & Derivatives: 1. Create a 10 minute lecture on a green chemistry topic related to your functional group. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your functional group.

1. Talk about making biodiesel from the triglyceride (Use of renewable feedstock, Waste Prevention)
2. Replace or add to the discussion of ester hydrolysis talking about biodiesel formation
3. Talk about using glycerol for other uses
4. Lead into a discussion about how how everything we use is derived from crude oil
5. Talk about

1. Greener oxidations of primary alcohols to COOH’s
2. Alternatives to addition of Grignard reagents to CO2 or to COOH derivatives
3. Greener amidation methods

10 minute green chemistry lecture

Green chemistry asides

Spectroscopy: 1. Create a 10 minute lecture on a green chemistry topic related to your topic. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your topic.

• GCP 11: NMR in tube (benchtop) for reaction analysis (GCP 6 for NMR itself)
• Describe NMR reaction monitoring vs TLC monitoring
• GCP 1: IR: ATR vs traditional (KBr, nujol, salt plates, etc)
• Describe traditional methods for liquid and solid samples
• “ for ATR

If water-soluble, use D2O instead of CDCl3 and suppress water signal (proton NMR)

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Specialized NMR tubes with capillary inserts for deuterated solvents (bulk is not deuterated)

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Older purity methods (successive recrystallizations) vs qNMR

10 minute green chemistry lecture

Green chemistry asides

Stereochemistry: 1. Create a 10 minute lecture on a green chemistry topic related to your topic. Indicate which of the 12 Principles of Green Chemistry you would be teaching. 2. Highlight two or three places where you can insert a green chemistry aside while teaching about your functional group.

When discussing synthesis of drug molecules we can bring in how we may only want one stereoisomer - have students read that one textbook chapter? Or we can just use our 10 minutes to summarize

Look at presidential green chemistry awards from the last 10 years

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Pick one topic that has a stereocenter in it and talk about how they made the thing

Taxol has a bunch of stereocenters and so we can also look at biocatalysts

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Sertraline can also be used for this example

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2 minutes where the students look up a drug or something and we can have them look for or show them a traditional synthesis route

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5 minutes on the 12 principles of green chem - highlighting principles of catalysis, waste prevention, and reducing derivatives

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2 minutes for students to see if they can find better synthetic routes

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1 minute to bring everyone back together and see what they all found

Both in lecture and in lab, we can talk about how you’ll get both isomers and then we can talk abou how you might prevent getting both compounds so that it’s limited to one (waste prevention)

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Using a lot of real-world examples

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When you teach catalysis, same stuff as above

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We can always bring up DCM

10 minute green chemistry lecture

Green chemistry asides