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