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Topic: O3 in the presence of zinc and water?  (Read 12975 times)

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Offline Tootella

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O3 in the presence of zinc and water?
« on: June 25, 2008, 03:57:19 PM »
Hello!

We did an oxidation experiment in lab today.  As part of post-lab, we have to draw the structures of different cyclic alkenes that have been treated with a variety of compounds.

One of the questions asks: what will the product be if an alkene is treated with 1) O3 2) Zn, H2O

Everything I've read about O3 (ozonolysis) has the reaction take place in the presence of (CH3)2S (dimethylsulfide).  I know that that does a cleavage and can give ketones and aldehydes as products.  Will doing a reaction with O3 in the presence of Zn, H2O do the same thing, or will the presence of these things give a fully oxidized product? 

I'm sorry if this is not clear.  Let me see if I can summarize it...

Will treating an alkene with
 1) O3 2) (CH3)2S
or
1) O3 2)Zn, H2O

do the same thing?  Will the second option give a fully oxidized product? 

Offline CopperSmurf

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Re: O3 in the presence of zinc and water?
« Reply #1 on: June 25, 2008, 04:59:46 PM »
hey.

ozone in either zinc and water or dimethyl sulfide will cut that carbon carbon double bond and turn it into a double bond oxygen.
They both give out the same products.
That's cool that they let you do that in the lab!

The only thing I can think of that will give you a fully oxidized product is to add Cr(6+) in H2SO4.

Offline Tootella

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Re: O3 in the presence of zinc and water?
« Reply #2 on: June 25, 2008, 08:21:03 PM »
Thank you sooo much!!! :-*

Offline g-bones

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Re: O3 in the presence of zinc and water?
« Reply #3 on: June 26, 2008, 06:03:03 PM »
hey.

ozone in either zinc and water or dimethyl sulfide will cut that carbon carbon double bond and turn it into a double bond oxygen.
They both give out the same products.
That's cool that they let you do that in the lab!

The only thing I can think of that will give you a fully oxidized product is to add Cr(6+) in H2SO4.

Ozone and an alkyne should give the carboxylic acid right?

Offline macman104

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Re: O3 in the presence of zinc and water?
« Reply #4 on: June 26, 2008, 07:34:46 PM »
No.  Ozone is a mild oxidizing agent.  It will not reduce your compound all of the way to a carboxylic acid.

Offline CopperSmurf

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Re: O3 in the presence of zinc and water?
« Reply #5 on: June 26, 2008, 08:02:01 PM »
macman got it right.  :)

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