Answer:
N-pentane, 2-butanone, butanol, propanoic acid
Step-by-step explanation:
Benzene is the eluent, which is a nonpolar molecule, so it elutes nonpolar molecules. The separation will happen to the less polar to the highest polar compound.
N-pentane is a hydrocarbon, so it's nonpolar and will be the first to eluted by benzene. Second, will be 2-butanone, which is a ketone, and have only one polar center: the bond between O and C, which is not much polar, because they have close electronegativities.
The third will be butanol, which is an alcohol, and have the bond between O and H, which have a larger difference of electronegativities, so it's an extremely polar bond.
Finally, propanoic acid is the most polar compound because it is a carboxyl acid and has two polar centers, the bond between O and C, and between O and H.