Can ozonolysis ever generate carbonic acid?

  • Thread starter baldbrain
  • Start date
  • Tags
    Acid
In summary, the conversation discusses a chemical reaction in which 1-cyclopropylbut-4-en-1-ol undergoes ozonolysis followed by workup with H2O2, resulting in the formation of 3-hydroxy-3-cyclopropylpropanoic acid and carbonic acid instead of the expected methanoic acid. The conversation also touches on the properties of aldehydes and carboxylic acids, as well as the possibility of oxidation occurring in other cases. The person speaking also asks for assistance with another chemical reaction involving hydroxylation with osmium tetraoxide.
  • #1
baldbrain
236
21

Homework Statement


In one of my solved problems, 1-cyclopropylbut-4-en-1-ol undergoing ozonolysis followed by workup with H2O2 (without the Zn dust) gave 3-hydroxy-3-cyclopropylpropanoic acid and carbonic acid, instead of methanoic acid. Possible? How?
IMG_20180731_135615.JPG
 

Attachments

  • IMG_20180731_135615.JPG
    IMG_20180731_135615.JPG
    32.8 KB · Views: 558
Physics news on Phys.org
  • #2
Look at the methanoic acid molecule - HO-C(=O)-H - what does -C(=O)-H resemble? What kind of properties would you expect?
 
  • #3
Ok, so you mean it will exhibit properties of an aldehyde and carboxylic acid both...
I know aldehydes are very easily oxidised to carboxylic acids.
But then, I have never seen this before. We always used to stop at the methanoic acid by-product. So, does it happen in every case or is there something special about this one... maybe the groups present on the other side of the alkene double bond?
 
  • #4
Once you have a methanoic acid and a strong oxidizer it gets oxidized, that's all. Doesn't matter what was the other part of the molecule, it reacts completely separately after hydrolysis.
 
  • Like
Likes baldbrain
  • #5

1. Can ozonolysis ever generate carbonic acid?

Yes, ozonolysis can generate carbonic acid under certain conditions. Ozonolysis is a chemical reaction that involves the reaction of ozone (O3) with an organic compound. This reaction can produce a variety of products, including carbonic acid (H2CO3).

2. What are the conditions for ozonolysis to produce carbonic acid?

Ozonolysis can produce carbonic acid when the organic compound being reacted with ozone contains carbon-carbon double bonds (C=C) or carbon-carbon triple bonds (C≡C). These bonds are necessary for the formation of the intermediate compounds that eventually lead to the production of carbonic acid.

3. Can ozonolysis produce carbonic acid from any organic compound?

No, not all organic compounds can undergo ozonolysis to produce carbonic acid. Only compounds that contain carbon-carbon double or triple bonds can undergo this reaction. Additionally, the presence of other functional groups in the compound can affect the formation of carbonic acid and other products.

4. Is carbonic acid a stable compound produced by ozonolysis?

No, carbonic acid is not a stable compound and is typically formed as an intermediate in the ozonolysis reaction. It quickly decomposes into other products, such as aldehydes, ketones, and carboxylic acids, which are more stable than carbonic acid.

5. What are the potential applications of ozonolysis in generating carbonic acid?

Ozonolysis has various applications in the chemical industry, including the production of carbonic acid. This acid can be used as a starting material for the synthesis of other compounds, such as pharmaceuticals, fragrances, and plastics. It can also be used in the production of carbon nanomaterials and in environmental applications, such as air and water purification.

Similar threads

  • Biology and Chemistry Homework Help
Replies
3
Views
2K
  • Biology and Chemistry Homework Help
Replies
1
Views
1K
  • Biology and Chemistry Homework Help
Replies
4
Views
1K
Replies
2
Views
1K
  • Biology and Chemistry Homework Help
Replies
4
Views
1K
  • Biology and Chemistry Homework Help
Replies
7
Views
6K
  • Biology and Chemistry Homework Help
Replies
1
Views
1K
  • Biology and Chemistry Homework Help
Replies
10
Views
5K
  • Biology and Chemistry Homework Help
Replies
1
Views
2K
  • Biology and Chemistry Homework Help
Replies
6
Views
6K
Back
Top