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Which solvent will dissolve more in given solute:

1. Ethylene glycol (HOCH2CH2OH) in hexane(C6H14) or H2O

2. Diethyl ether (CH2CH2OCH2CH3) in H2O or CH3OH?

3. NaCl in CH3OH or CH3CH2CH2CH2OH

I know that like dissolves like. Therefore the molecules with the similar intermolecular forces will dissolve. However, I don't understand when it comes to the compounds above. For example,what would make them more polar or more non polar. I read somewhere that compounds with an OH at the end tend to be polar. Therefore:

1. would ethylene glycol more readily dissolve in water?
2. i have no clue
3. NaCl dissolves in water so I'm going with CH3OH.

Does the amount of H's in the chain affect polarity?

You are on the right track. Ethylene glycol, with the two OHs attached, easily dissolves in water. Diethyl ether isn't vry polar but CH3OH is less polar than H2O; therefore, I suspect the ether will dissolve easier in CH3OH. and I think you are right with NaCl. Have you tried looking this up on google? Just type in, for example, solubility sodium chloride water or solubility sodium chloride methyl alcohol or solubility sodium chloride various solvents.
As for more polar or non-polar:
For similar compounds, such as CH3OH vs CH3CH2OH, both are polar but the longer chain makes it less polar; that is, it is more "hydrocarbon" and no more polar OH. For ethers vs alcohols, the O in ethers hinders the oxygen but the OH is on the end where it can hydrogen bond with alcohols. That kind of thing is what you look for. As for google, it is a good reference for checking yuor thinking but, of course, you want to be able to look at these things and make an educated guess.

thank you!

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