ToScore OC Test#2 Q71 Wich is most soluble in pentane

[Dentista08]

I don't get why is

more soluble in pentane than

I understand that its because ether is nonpolar, but 1,4 Diaminobenzene looks non-polar to me also, since it's symmetrical? I'm missing something here...

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[dentalplan]

im not positive so dont hold me to it...but maybe its because since pentane is not a suuuuper long hydrocarbon (kinda short) it resembles water more than it does a long hydrocarbon like decane, etc.

Since its more like water...its gonna make Hydrogen bonds with that first molecule....rather than non-polar bonds to the diamino molecule ...