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Topic: Oxidated compound  (Read 2029 times)

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Offline Rutherford

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Oxidated compound
« on: November 07, 2012, 11:33:52 AM »
When geraniol is vigorously oxidized, three products are obtained: (they are attached).
Determine the structural formula of geraniol (C10H18O).

I know that the carbonyl groups from the products are made from C=C bonds. When I count the number of C atoms I get 9, but it should be 10. I thought that it is cyclic maybe, but it isn't. How to solve this? Where the OH groups came from if geraniol has only 1 oxygen?

Offline discodermolide

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Re: Oxidated compound
« Reply #1 on: November 07, 2012, 11:39:12 AM »
What does vigorously oxidised mean? Ozone, permanganate, periodate?
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Offline Rutherford

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Re: Oxidated compound
« Reply #2 on: November 07, 2012, 12:13:26 PM »
I don't know. It isn't said. Is it so important? Either way, it is cleavage oxidation probably.

Offline discodermolide

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Re: Oxidated compound
« Reply #3 on: November 07, 2012, 12:15:31 PM »
I'm not sure you can loose just 1 C atom, perhaps it's an error?
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Offline Rutherford

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Re: Oxidated compound
« Reply #4 on: November 07, 2012, 12:23:42 PM »
I think that it is ozonolysis with H2O2 (that's why the extra OH groups are formed).
I was solving now a similar problem, where I had the reactant and to guess the products. I tried to do it by looking at this one, but when I checked the answer I saw that I missed formic acid. Maybe it is made in this problem, too, only it wasn't given.

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