My attempt at a solution:
First I look for hydrogen bonds:
The only compounds with hydrogen bonds are the second and fourth ones, so they have the strongest intermolecular forces. The second must have stronger intermolecular forces since it harbors three hydrogen bonds, while the fourth only has room for two.
Then I look for dipole-dipole interactions:
The first compound has the potential for a dipole-dipole moment. It would be the third strongest.
Then I look for potential for London-dispersion forces:
The third compound and The fourth experience London-dispersion forces. But I'm stuck on discerning which is stronger.
So, my working solution is: 3, 5, x, 4, x