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Topic: Ozonolysis  (Read 7101 times)

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Offline Pranav

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Re: Ozonolysis
« Reply #15 on: January 23, 2013, 05:10:28 AM »
Also, dialdehyde is not given as an answer in any of the options given with this question.

Can you post the options given with the question?

The options are:
a. Cyclohexanone
b. Cyclopentanone
c. Cyclohexanol
d. Hexane-1,2-dicarboxylicacid.

Offline discodermolide

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Re: Ozonolysis
« Reply #16 on: January 23, 2013, 05:16:15 AM »
The only thing it can be is d, Hexane-1,2-dicarboxylicacid.
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Offline orgopete

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Re: Ozonolysis
« Reply #17 on: January 23, 2013, 11:29:25 AM »
In that case, I think cyclopentanone could be the product.

This would be my thinking. Because ozone is the second step, then elimination must be occurring (if NaNH2/NH3 were the reagent, this would seem more plausible, none the less). Ozone formally gives a dialdehyde plus H2O2. H2O2 plus an aldehyde gives an aldehyde acid (plus some diacid). If BaO were not present, then the diacid seems plausible, but it would form a salt with barium. No aldol products are listed so it cannot be an aldol product of the dialdehyde. An intramolecular Claisen of the enolate of the aldehyde could give 2-oxocyclopentanecarboxaldehyde. A retro-Claisen by attack upon the aldehyde could liberate Formica acid and give the enolate of cyclopentanone. Tautomerization and neutralization would give te ketone. Just guessing.
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