ozonolysis followed by H2O2 or hydrogen peroxide...?

Question

what would be the name of the alkene which gives the following products ( i wish i can draw the structures out for u but use your imagination) followed by the treatemn with H2O2.:

a cyclohexane with an oxygen doubley bonded to the 1st carbon and the 2nd carbon so that it to oxygens

and
O O
|| ||
HO-C-C-OH the oxygens are doubly bonded one to each carbon.

I tried to come up with an answer and looked in a book and on various websites but i dont see an example of this type of ozonolysis at all

u have me confused about diene. but yes books and websites do show H2O2 as the oxidising agent.

Answer 1

Ozonolysis is breaking the double bond C=C using ozon (O3).
R1 .. .. .. R3.. .. .. .. .. .. .. R1 .. .. .. .. .. .. R3
.. .. \ .. .. / .. .. .. .. .. .. .. .. .. \ .. .. .. .. .. ../
.. .. .C=C .. + O3 ->-> .. .. ..C=O .. O=C
.. .. / .. .. \ .. .. .. .. .. .. .. .. .. ./ .. .. .. .. .. ..\
R2 .. .. .. .R4 .. .. .. .. .. .. .. R2 .. .. .. .. .. R4

I put 2 arrows because there are more than one steps to get to the products.
Depending on the substituents on the C atoms the products will be either ketones and/or aldehydes.
Treating these products with H2O2 will not affect ketones but will oxidize aldehydes to carboxylic acids.
So HO-C-C-OH
.. .. .. .. ||..||
.. .. .. ..O.O

comes from
H-C-C-H
.. .. ||..||
.. .O.O

Look at the reaction I have wiritten above. In order to find the original alkene you just need to fuse the ketones and aldehydes through the carbonyl groups. If you did that you would get a 6 member ring fused to a four member ring that has also 2 double bonds. This is not really possible. .
.. .__
../.. .. \
..\___/
.. ll__ll


However if you consider that from the ozonolysis you get 1 molecule of the 1,2-cyclohexadione and 2 molecules of HCOCOH, then you get a 6 member ring fused to a benzene ring

.. .__
../.. .. \
..\___/
..//.. .\\
..\ ...../
... ==
I am sorry but I can't draw it better. If you cut the molecule at the double bonds and put C=O where you had C=C you'll see that you get the desired molecules. I'll put asterisks at those points to help you, though I can't really cut the sideways double bonds in the middle as I should

.. .__
../.. .. \
..\___/
..//.. .\\
*** ...***
..\ .. .. /
.. .=*=

Answer 2

Ozonlysis is used to cleave Carbon-Carbon double bonds by oxidation. When you cleave the double bond, you get a carbonyl function on the first carbon of the double bond. I'm not sure about what H2O2 does, but I know that in the presence of an acid, the carbonyl will be further oxidized to a carboxylic acid.

So....If yu have 1-5, hexadiene, and you add ozone, the double bonds between carbons 1-2 and carbons 5-6 will be cleaved, leaving you with a carbonyl group (C=O) on Carbons 1 and 6. I'm assuming that, in the presence of H2O2 (I don't know for sure...but it makes sense), that it would somehow cause a radical rxn to occur at either end that would make the molecule cyclize, connecting carbons 1 and 6 to form a ring. Since those are the ones you have the carbonyls on from the ozonlysis, you would subsequently get a cyclohexane molecule with C=O in carbons 1 and 2.

Hope that helps!