The question requires us to rank the intermolecular interaction present in the molecules given, from the weakest to the strongest.
To answer this question, we need to keep in mind that the force of intermolecular interactions follows this order:
ion-dipole interactions > hydrogen bonding > dipole-dipole interactions > Van der Waals forces
Let's number the molecules given from I to IV, starting from the left.
We can notice that molecules I and II present hydrogen bonding (in the image, the bond is represented with F, a very electronegative element), while molecules IV presents ion-dipole interaction and molecule III presents London dispersion forces
Next, we need to compare the electronegativity between molecules I and II:
- Because of the cyclic structure, the electron density in molecule II would be more concentrated over the O compared to the O in molecule I - therefore, the intermolecular interaction in molecule II should be stronger compared to molecule I
Considering the information above, we could rank the intermolecular interaction present in the molecules given from the (weakest to the strongest) as: III < I < II < IV (London dispersion forces < hydrogen bonding in molecule I < hydrogen bonding in molecule II < ion-dipole interaction)