Imagine a reaction that can replace one hydrogen atom of an alkane at random with a chlorine

Question:

Imagine a reaction that can replace one hydrogen atom of an alkane at random with a chlorine atom.

If pentane were subjected to such a reaction, how many different compounds with the formula C5H11Cl would be obtained? Give their Lewis structures. Then build models (or draw wedge-dashed wedge formulas) for each compound.
Provide the same analysis carried out on 2.2-dimethvlbutane.