Your priorities are wrong:
The first example (from highest to lowest): OH > phenol > benzene > CH3, its S so you got your answer correct
The second example: NH2 > iPr > Me > H, again S
The way it works is that you look at the one atom that is bonded to the chiral center to see if they can be distinguished: in the first example its 3 carbons and one oxygen. Oxygen has higher priority therefore its no.1, then you continue through the chain from the carbons in the direction of the highest priority. Its clear that the methyl group has only hydrogens while the other two continue with carbons. THerefore, the methyl group has lower priority and we can designate in no. 4. To distinguis between the remaining two, we just do the same and we end up with those two atom chains:
"C-C-C-O" for phenol and "C-C-C-C" for benzene. THe oxygen has higher priority than carbon, therefore phenol is no. 2 and benzene no.3
THe other example is bit simpler: NH2 is no.1 while H is no. 4. Then you differentiate between the remaining two and you end up with chains "C-H" for methyl and "C-C" isopropyl, making the isopropyl no.2 and methyl no.3
hope it helps. You can try the remaining two by yourself