Peroxide in acidic conditions being reacted with iron sulphate mechanism
At least for the second part of the product formation, you have pretty much given the answer yourself.

The methylcyclopentane moiety of the products results from two different 5-exo-trig radical ring closures, that is from the intramolecular addition of two different radicals to $\ce{R-\color{\red}{C}H=CH2}$. 

How are these two different radicals generated?

Have a look at the starting materials! Isn't the combination of the hydroperoxide $\ce{R-OOH}$ and $\ce{FeSO4}$ very similar to the conditions of a Fenton reaction?

Let's therefore postulate the following: $\ce{R-OOH + Fe^2+ -&gt; R-O* +\quad{}OH-  + Fe^3+}$

The resulting 1-methylcylohexan-1-ol derived radical can form methyl ketones by cleaving two different $\ce{C-C}$ bonds; the resulting carbon-centered radicals then give rise to the different cyclization products.