These answers are not mine....they're the official ones.
For my answer, I actually put them, in order in the question, 1, 3, 5, 4, 2...
I thought the third and fourth one would be most stable because they have the most number of resonance forms. Then, I thought what would stabilize the negative charge, by taking away the negative density. And the chlorine atom would be better than CH3, which would be better than OCH3. I found this order in the substitute benzene reactivity list, which represents which substitutes would donate electrons, and which substitutes would take away electrons.