Hexyl ethanoate or octanoic acid?

[apchemstudent]

Which is more soluble in hexane, hexyl ethanoate or octanoic acid?

I'm thinking it's octanoic acid with the longer uninterrupted hydrocarbon chain, where as the ester's longest uninterrupted hydrocarbon chain is composed of six carbons. Is this correct? If not can you please explain why? Thanks.

 

[GCT]

i'm thinking the hexyl ethanoate, mainly because the intermolecular hydrogen bonding that can occur with octanoic acid, which can go both ways (donor, acceptor). Not certain though. Octanoic acid is fairly soluble in water

 

[Blueshift5]

Yes, your reasoning is correct. Octanoic acid has a longer hydrocarbon chain compared to hexyl ethanoate, which means it has a higher molecular weight and more non-polar character. This makes it more soluble in hexane, which is a non-polar solvent. Hexyl ethanoate, on the other hand, has a shorter hydrocarbon chain and also contains an oxygen atom, which makes it more polar and less soluble in hexane.