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Ranking question about solubility

by sgstudent
Tags: ranking, solubility
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sgstudent
#1
Feb25-13, 02:44 AM
P: 645
Rank the following of increasing solubility in acetone, (CH3)2C=O
A. Oxygen B. CH3CH2CH2OH C. HOCH2CH2CH2OH

I know that acetone has dipole-dipole interactions but it is capable of hydrogen bonding as it has 2 hydrogen bond acceptors. So in A, there are only London Dispersion interactions so it is hardly soluble in acetone. But I'm having problems with comparing B and C. The reasoning is below and I hope you guys can clear out my misconception.

If I have an 1 to 1 ratio of acetone and propanol, there is a total of 1 hydrogen bond acceptor and 4 hydrogen bond acceptors. The maximum number of hydrogen bonds is 1. This is the same as in propanol so they are very soluble in each other.

While in an 1 to 1 ratio of acetone to 1,3-propandiol, there is a total of 2 hydrogen bond donors and 6 hydrogen bond acceptors. So the maximum number of hydrogen bonds is 2. This is also the same in the diol so they are also very soluble in each other.

So in both cases, they are equally good as the strongest interactions in the solution is the same as in the strongest interactions in the solute or solvent. So how should I tell which molecule is a more soluble in acetone? In my mind I'm thinking that they should be equally soluble.

How should I understand why the diol is more soluble in the acetone? Thanks
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