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 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? It's 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 about evaporating because it's frozen, and 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 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 can make carboxylic acids. I think those are two pretty cool choices. Go science. Let's move on to the next video.
22. Carboxylic Acid Derivatives: NAS
Carboxylation
22. Carboxylic Acid Derivatives: NAS
Carboxylation - Video Tutorials & Practice Problems
Let's learn a really cool way to make carboxylic acids! Are you ready?
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concept
Carbonation of Grignard Reagents
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Problem
ProblemDetermine the major product for the following reaction.
A
B
C
D
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PRACTICE PROBLEMS AND ACTIVITIES (13)
- Using the given starting material, any necessary inorganic reagents, and any carbon-containing compounds with ...
- Show how the following compounds could be prepared from the given starting materials. You can use any necess...
- Show how each of the following compounds can be prepared, using the given starting material: f.
- What are the products of the following reactions? i.
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- Show how you would accomplish the following multistep syntheses, using the indicated starting material and any...
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- Show how you would accomplish the following multistep syntheses. You may use any additional reagents and solve...
- (••••) When a chemist attempted the following reaction sequence, the desired product was not formed. (a) Why? ...
- Using bromocyclohexane as a starting material, how could you synthesize the following compounds? c.
- Show how you would synthesize the following carboxylic acids, using the indicated starting materials.(d) butan...
- Show how you would synthesize the following carboxylic acids, using the indicated starting materials.(f) allyl...