Is there a way to generalize the solubility of any organic compound based on their functional groups and the length of their carbon chains? I know that beyond 3 carbons, alcohols are insoluble, and beyond 4 carbons, carboxylic acids are insoluble. But what if the alcohol had 2 hydroxyl groups? What if the carboxylic acid had 2 carboxyl groups? How many carbons would they each need for the compound to become insoluble in water again? Are there any quantitative guidelines for determining this?
And what about the solubility of esters and haloalkanes? How many carbons does an ester and haloalkane need to have for them to be insoluble? Again, what if there are multiple ester or halide groups?
Lastly, how do you determine solubility when you’ve got a mixture of functional groups? Take aspirin for example, whose structure contains a benzene ring of 6 carbons, a carboxyl group attached to one corner, an ester group attached to another corner, and one methyl group attached to the ester. How would you systematically determine if this compound was soluble in water or not?
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