Ranking question about solubility

[sgstudent]

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

 

[jbsteele]

A. Oxygen B. CH3CH2CH2OH C. HOCH2CH2CH2OH The increasing order of solubility in acetone is A < B < C. This is because the oxygen has no hydrogen bonding capabilities, while both CH3CH2CH2OH and HOCH2CH2CH2OH can form hydrogen bonds with acetone molecules. However, the diol (C) has two OH groups that can form hydrogen bonds with acetone, which makes it more soluble than the monohydric alcohol (B).

 

[jbsteele]

A. Oxygen B. CH3CH2CH2OH C. HOCH2CH2CH2OH The answer is A < B < C, with increasing solubility in acetone. This is because oxygen has the weakest intermolecular forces since it has no hydrogen bonding or dipole-dipole interactions. Meanwhile, propanol and 1,3-propanediol can form hydrogen bonds with acetone due to their polar nature, and the diol has two more hydroxyl groups than the alcohol, allowing it to form twice as many hydrogen bonds. This makes it more soluble in acetone than propanol.