predict whether a non-polar compound or polar compound is more easily separated into molecules
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Non polar compounds are more easily separated into molecules.
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The simple answer is that you can't. There are basic rules of thumb, but that's it. To get any reasonable degree of accuracy would require detailed calculations regarding how the solute will interact with the solvent, which could only be performed by a computer.
The most important rule is that like dissolves like. Water dissolves polar compounds. Organics dissolve organics. Mercury dissolves some metals (but not all).
A rule of thumb for when an organic compound will be soluble in water: count the number of carbons and divide by the number of polar functional groups. If the answer is less than five then the compound is likely to have good solubility in water. Five or more, probably not so good. Where does this number 5 come from? Data. No way you could predict it if you didn't know.
For ionic compounds dissolving in water there are common rules you can find in most introductory textbooks. Pick the first rule that applies:
Almost all alkali metal salts are soluble, as are ammonium salts
Almost all nitrate salts are soluble
Almost all remaining lead, mercury(I), and silver salts are insoluble
Almost all remaining sulfides and carbonates are insoluble
Most remaining chlorides, bromides, and iodides are soluble. (Exceptions include copper(I) chloride)
Most remaining sulfates are soluble, but not those of strontium and barium. Calcium sulfate is sparingly soluble.
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