Why does hexane dissolve in acetone

Why does acetone (propanone) dissolve in heptane?

Hello dear community,

I recently wrote an ex in chemistry (Q11 Bavaria) and I am not satisfied with the evaluation of one task, which cost me 2 grade points (only 13 instead of 15).

The question was: "Explain the difference between the boiling points of benzene (80.2 ° C) and phenol (182 ° C)!"

My answer to this: (including the limit structure formula of phenol)

Phenol has significantly stronger intermolecular interactions than benzene and can therefore only boil with higher energy. Due to the lack of polarity, benzene only enters into VdW forces and is therefore easier to boil, i.e. only the mass and surface are decisive. Phenol, on the other hand, has a positive charge on the oxygen of the OH group and an alternating negative charge on the 2,4 or 6th carbon of the ring due to its boundary structures (5 in total) (due to the + M effect). That is why the phenol interacts with one another in an ion-like manner. Since this negative charge is short-lived or only exists for a short time, the normally strong ionic bond is only so weak that 182 ° C is sufficient for boiling. The positive charge, on the other hand, is relatively common on oxygen. "

That gave 0.5 out of 2 valuation units.

The teacher's "horizon of expectation": "This is because of the polarity of the OH group (read: H-bridges)."

But I have strong doubts that the OH group is "to blame": 1. Due to the frequent positive charge on O, no H-bridges are possible, because it must be negative so that the positively polarized H atoms can interact . 2. The ring has too much mass for the OH group to achieve a noticeable effect (cf. hexanol is also non-polar despite the OH group) 3. H-bridges do not have an effect of boiling temperature around 100 ° C differs at this mass.

In response to my question (with my above-mentioned objections), the teacher said why my logical explanation is wrong: "He doesn't know exactly either, but it is in every book"

Please help me, I have to convince the teacher to give me the points or at least 1.5 / 2 so that I get 14 or 15 grade points on the Ex. - best with evidence -

Wrong I should be wrong, please provide me with counter-evidence and I accept the grade.

Please reply / help quickly!

Thanks in advance

Greetings schueler123456

P.S .: If I knew how to write chemical formulas here, I would insert the boundary structure formula of phenol.