[Phase5]

I did a lab and discovered that most of the polar organic compounds I tested would dissolve in water, HCl, NaOH and NaHCO₃, but not in ethyl acetate. There were however organic compounds that did the opposite. All but one were aromatic compounds, the exception being butyraldehyde. I would think that ethyl acetate, only being able to be the acceptor of hydrogen bonds, would have difficulty dissolving other acceptors - but instead it is aromatic compounds it has difficulty with. Why is this? And why didn't the other compounds dissolve in ethyl acetate?

[nikium]

What does it mean chemically to dissolve? To dissolve is to form intramolecular bonds (the same kind of intramolecular bonds that are broken when you boil something) between molecules that exist in a solution. Specifically, forming hydrogen bonds. Hence, to dissolve, both the solute and the solvent must have hydrogen bonds in their structures. Recall that hydrogen bonds are, H-O, H-N, or H-F bonds.

Next, to decide whether something will dissolve, you have to be comfortable with drawing the structures of compounds. Water, HCl, NaOH and NaHCO3 all have hydrogen bonds. (prove this to yourself). Ethyl acetate, on the other hand does not:(even though it have two oxygens, none of the oxygens are connected to a hydrogen):

I am not sure about the aromatic compounds. It depends on what they are. If it's just benzene, then we can expect that, having hydrogen bonds, it will not dissolve. If the aromatic compound is phenol (a benzene with an -OH) it will dissolve in water slightly.

[Phase5]

Oh sorry, I meant to write that ethyl acetate had difficulty dissolving organic compounds that did NOT have an aromatic ring. 

Butyraldehyde, aniline, benzaldehyde, 4-aminobenzoic acid and benzoic acid would dissolve (or at least dissolve slightly) in ethyl acetate. However, acetone, carbamide, glucose, sodium acetate, butanone, sodium carbonate and lactose would not.

If I've understood correctly ethyl acetate is less polar than water. Is that the reason that compounds with an aromatic ring would dissolve in it? Because they were not so polar as well (like likes like)? Meaning that the compounds without an aromatic ring would not dissolve because they were TOO polar?

But I thought ethyl acetate was able to accept hydrogen bonds, but not to be the one that donates a hydrogen bond since it has a carbonyl group (and therefore polar). Should it not dissolve all polar compounds then? Or is it that it is considered non-polar and the compounds with aromatic rings are non-polar as well?

Sorry for all the questions...