Oxidative Cleavage by Ozonolysis

[shane.]

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H'okay, so from what I understood,

Cleaving alkenes by treatment with ozone and zinc will yield two aldehyde products.

However, when cleaving alkenes by treatment with ozone alone, oxidation will occur all the way to two carboxylic acid products.

Topscore says my understanding is wrong.

👎

 

[Flipper405]

I'm sorry to say that I have to side with topscore on this one.
The treatment with ozone does not actually cleave the bond; it creates a five-membered complex of three oxygens and 2 carbons as you can see from this picture (thanks wikipedia):

The Zn is part of the reductive workup where the ring is cleaved to form the carbonyls.

Perhaps where you were led astray is the ozonolysis of alkynes, where two carboxylic acid groups are formed:

 

[shane.]

Perhaps where you were led astray is the ozonolysis of alkynes, where two carboxylic acid groups are formed:

That's it. Haha, thanks.

I specifically knew while taking the test I had made a flashcard of a specific ozonolyis reaction that did not use Zn and that two carboxylic acids were the result.

Looks like I need to go through my flashcards, once more.