Ozonolysis

[SaintJude]

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Q from Kaplan's LOD

How many ketone, aldehydes and COOH groups are found in the product?

How do you figure this out? And I mean "MCAT-style quickly" b/c ozonolysis isn't a mechanism I think we need to understand.

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Here's my thinking:

alkene reactant = 2 carbonyls products. So I know in total there will be 8 carbonyl compounds...But that's it.

 

[chaser0]

Is the answer 5 Ketones, 1 Aldehyde, and 2 Carboxylic acids?


Ozonolysis splits the double bonds, turning each C=C into a C=O + O=C
I think.... it's been a while.

 

[SaintJude]

Yup, and thanks I think i understand it now.

I had to draw out the H to actually see where the aldehyde would form
And I also had to realize that the OH as a substitutent would form a carboxylic acid instead of a ketone.

Thanks.

 

[folktale]

Okay so I see that the carboxylic acids are formed from the double bonds that has an -OH, but I can't tell where the aldehyde would be formed. Can someone explain it?

 

[pfaction]

Okay so I see that the carboxylic acids are formed from the double bonds that has an -OH, but I can't tell where the aldehyde would be formed. Can someone explain it?

Top right most has a hydrogen sticking out. Aldehyde.

 

[folktale]

Top right most has a hydrogen sticking out. Aldehyde.

Thanks pfaction! 👍