[jorbarrientos]

Hi, I was wondering if someone can help me, the thing is im new to organic chemistry and i need to understand why´s that benzoic acid disolves in toluene, and how is it that this happens... ive tried to look it up everywhere but theres nothing useful that answers my question, at least not something i can understand yet. I would really appreciate it if someone helps me with this explaining it in a really simple way. thanks  

[Arkcon]

Can you find something of a hint from drawing out their structures?

[jorbarrientos]

yeah, i see they both have a benzene ring, but i would like to understand how does that make benzoic acid soluble in toluene. i mean, why and how does that happen if its not too much to ask. It might sound stupid to ask this but im really new to this.

[Arkcon]

Do a little searching on pi-bond stacking.  Its an important concept to understand, because it has a variety of applications.

[jorbarrientos]

Thanks, ive been reading about it, and i have one more question, does this pi-bond stacking between aromatic rings affects the solubility of benzoic acid in toluene or that has no other explanation than the polarity of molecules?

[Arkcon]

Well, can you compare the polarity of toluene and benzoic acid?  That sounds like a good exam question, you should write out a response so that you're ready.