Isopentane Cl2 substitution reaction

[pigwiddeon]

Hello,

I have a question. Let's say we have isopentane and Cl2 in a substitution reaction. How many different Carbon atoms can chlorine atom bond with? All five or can it substitute with a hydrogen that bonded to methyl brach?

It is an easy question maybe but please answer that is really important for me.

Thanks for your consideration.

 

[sjb-2812]

Theoretically? Or practically? Why not try drawing out all, naming them and seeing if they're different?