Can ozonolysis ever generate carbonic acid?

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Discussion Overview

The discussion centers on the ozonolysis of 1-cyclopropylbut-4-en-1-ol and whether this reaction can produce carbonic acid alongside 3-hydroxy-3-cyclopropylpropanoic acid, particularly in the context of the reaction's by-products and mechanisms involved.

Discussion Character

  • Homework-related, Technical explanation, Conceptual clarification

Main Points Raised

  • One participant describes a specific ozonolysis reaction that yields both 3-hydroxy-3-cyclopropylpropanoic acid and carbonic acid, questioning the typical outcome of methanoic acid.
  • Another participant notes the structural similarities of methanoic acid to aldehydes and suggests it may exhibit properties of both aldehydes and carboxylic acids.
  • A participant expresses uncertainty about the reaction's typical outcomes, wondering if the presence of specific groups on the alkene affects the by-products.
  • One participant asserts that methanoic acid can be oxidized by strong oxidizers, implying that the reaction's context allows for different products, but does not clarify if this is universally applicable.

Areas of Agreement / Disagreement

Participants do not reach a consensus on whether carbonic acid is a common by-product of ozonolysis in this context, and there are competing views regarding the influence of molecular structure on the reaction outcomes.

Contextual Notes

Participants express uncertainty regarding the conditions under which carbonic acid might be produced, and there are unresolved questions about the influence of specific substituents on the alkene structure.

baldbrain
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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?
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Look at the methanoic acid molecule - HO-C(=O)-H - what does -C(=O)-H resemble? What kind of properties would you expect?
 
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?
 
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.
 
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