[Rutherford]

When geraniol is vigorously oxidized, three products are obtained: (they are attached).
Determine the structural formula of geraniol (C₁₀H₁₈O).

I know that the carbonyl groups from the products are made from C=C bonds. When I count the number of C atoms I get 9, but it should be 10. I thought that it is cyclic maybe, but it isn't. How to solve this? Where the OH groups came from if geraniol has only 1 oxygen?

[discodermolide]

What does vigorously oxidised mean? Ozone, permanganate, periodate?

[Rutherford]

I don't know. It isn't said. Is it so important? Either way, it is cleavage oxidation probably.

[discodermolide]

I'm not sure you can loose just 1 C atom, perhaps it's an error?

[Rutherford]

I think that it is ozonolysis with H₂O₂ (that's why the extra OH groups are formed).
I was solving now a similar problem, where I had the reactant and to guess the products. I tried to do it by looking at this one, but when I checked the answer I saw that I missed formic acid. Maybe it is made in this problem, too, only it wasn't given.