[horsebox]

From what I've gathered the halogen free radical is most likely to rob a hydrogen off the carbon that makes the most stable free radical and the carbon that makes the most stable free radicals are quaternary while the least stable are primary carbon free radicals. How do you know whether a product will be monohalogenated, dihalogenated etc.?

[Schrödinger]

How do you know whether a product will be monohalogenated, dihalogenated etc.?

You don't there's always a mixture of products in a free radical reaction. For instance, free radical chlorination of methane produces mono, di, tri and tetra chloromethane, but not necessarily in equal amounts

[Thujone]

From what I've gathered the halogen free radical is most likely to rob a hydrogen off the carbon that makes the most stable free radical and the carbon that makes the most stable free radicals are quaternary while the least stable are primary carbon free radicals. How do you know whether a product will be monohalogenated, dihalogenated etc.?

Also keep in mind that a teriary carbon radical is the most stable, quaternary can't be a radical.