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

...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

Identical university and apparently identical answers.

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.

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.