Solubility

[chiddler]

Look at this beast of a molecule

http://en.wikipedia.org/wiki/Fluorenone

look how hydrophobic it is! with one measly ketone. ha. ha. water laughs at you.

So if I were to ask in which solvent is this thing more soluble in, acetone or cyclohexane, why is it more soluble in acetone?

Sure like dissolves like, but acetone, relative to this molecule, contains much more polarity. This is overwhelmingly non-polar and I would like the answer to be cyclohexane.

Why am I wrong?

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[Buttafuoco]

If that's the case, I'm thinking resonance. Push that double bond on the carbonyl up onto the O and look at the options for resonance stabilization.

 

[syoung]

I concur. Fluorenone has a lot of resonance that gives it stability but also higher degrees of polarity, hence acetone for solvent. Cyclohexane is 100% polar, no resonance.

 

[chiddler]

i missed resonance. that's a good catch.

I concur. Fluorenone has a lot of resonance that gives it stability but also higher degrees of polarity, hence acetone for solvent. Cyclohexane is 100% polar, no resonance.

you mean non-polar

thanks for the responses.