Guidelines for Solubility in Water of Organic Compounds in Relation to Carbon Chain Length
To determine the solubility of some compound, a chemist would systematically throw it into water and see what happens. You may draw some correlations like "plus six for two hydroxyls, minus five for five carbons, should be soluble"; they are somewhat useful, but mostly qualitatively.

There is a whole hierarchy of computational methods for prediction of solubility, but these are highly complicated.

BTW, haloalkanes are almost as insoluble in water as alkanes themselves.