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Can ozonolysis ever generate carbonic acid?

  • #1
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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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Answers and Replies

  • #2
Borek
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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?
 
  • #3
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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
Borek
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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.
 
  • #5
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