Need help with structures

[azazel2113]

Hello, I need help with a problem that involves drawing structures.

 

The question is

 

Compound A with a molecular formula of C6H10 decolorizes Br2 and produces a precipitate when reacted with permanganate solution. Hydrogenation with H2 over Pd/C produces B with a formula of C6H12. Reaction of A with peroxyacetic acid produces C, which is highly strained. Hydration of C produces D. Reaction of A with osmium(VIII) oxide followed by work-up produces E which is an isomer of D. C can also be produced by addition of A to bromine water followed by heating. Ozonolysis of A produces a single product E which is a symmetrical diketone.

 

Draw structures for A,B,C,D,and E.

 

This is what I have so far. I am confused because I do not have a mechanism involving heating bromine water. and when I do the ozonolysis of A I do not get the same compound as the E I got from the Os reaction. Any help would be greatly appreciated

[Horza2002]

...theres already a thread with these exact same questions on:

 

http://www.scienceforums.net/topic/61949-mechanisms-help/

 

I take it you two are at the sam University then

[hypervalent_iodine]

Identical university and apparently identical answers.

[azazel2113]

Sorry for that guys,we do go to the same school and were pulling an all nighter review before a test. On this question, I did not know she had posted the work (probably due to lack of sleep) so I posted it. Won't happen again.

[hypervalent_iodine]

That's alright! Have a look at the link Horza posted if you haven't already. We've given Jessica a bit of help in there, so you can post any other questions you have in her thread. Hope you both got or are getting some sleep before the exam.