Ch. 20 - Carboxylic Acid Derivatives: NAS WorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

Let's learn a really cool way to make carboxylic acids! Are you ready?

Concept #1: Carbonation of Grignard Reagents

Transcript

In this video, I’m going to quickly discuss a really cool way to make carboxylic acids and that's through carbonation of Grignards. It turns out guys that Grignard reagents are really great nucleophiles. They have a very strong negative charge on the R. When they’re exposed to dry ice, what is dry ice? Cold, it’s not real ice. It’s frozen CO2 gas. When you literally pour a Grignard on frozen CO2 gas, what's going to happen? It turns out that CO2 acts like an electrophile just like a carbonyl does. In fact, it's an even stronger electrophile because it has these two extremely strong dipoles. When the Grignard sees the carbon dioxide that’s evaporating because it’s frozen, you’re pouring a liquid on it, the R is going to attack the carbon and push electrons down. What we're going to get is a molecule that now looks like this. I've got my carbonyl, I've got my O negative, and I’ve got my R. Check that out.
In just one step, I went from something that looks nothing like a carboxylic acid to a carboxylate. That's what this is, I get a carboxylate. Now, all I need is a protonation step to take care of the rest. I would use whatever I want to protonate my carboxylate and I just made a carboxylic acid from dry ice. Pretty cool, right? If you put dry ice in your pool, then it makes that dry ice vapor that hangs over the pool. I’m not sure if you guys have seen that. Or you could just pour a Grignard on it and you could make carboxylic acids. I think those are two pretty cool choices. Go science. Alright, so let’s move on to the next video.

Practice: Determine the major product for the following reaction.