[yogurtspoon]

The question asks whether 1) boric acid and 2) 1-hexanol would be more soluble in diethyl ether or aqueous solvent (which just means water right?).

For boric acid, I thought it'd be more soluble in water - since boric acid is polar, and it can hydrogen bond with water but not diethyl ether.

For 1-hexanol, I know the OH group would make it slightly polar, but wouldn't the hydrocarbon chain decrease its solubility in water? So I thought maybe diethyl ether would be the better choice since it's a nonpolar solvent. But is the opportunity for hydrogen bonding in water more important? Not sure if I'm just overthinking this part.

Thanks in advance for any help.

[rolnor]

I think you are right and its good to do some overthinking. Boric acid is a bit strange sometimes but it should prefer water, hexanol will mainly be in ether but some in the aqueous phase I think.

[Babcock_Hall]

@OP, Can there be any hydrogen bonding between hexanol and diethyl ether?

[yogurtspoon]

@OP, Can there be any hydrogen bonding between hexanol and diethyl ether?

Now that you asked I'm not totally sure... I thought there would have to be an H on diethyl ether's O for it to hydrogen bond with hexanol?

[Babcock_Hall]

Think in terms of H-bond donors and acceptors, and draw it out.

[yogurtspoon]

Okay drawing it out helped I think – so the O in diethyl ether would be the H-bond acceptor, and the OH group in hexanol would be the donor. Thanks for pointing this out!

[Babcock_Hall]

Yes.  These sorts of interactions help explain why one finds more ethyl acetate or diethyl ether in water (after an organic extraction) than one finds hexane.