The solubility of an alcohol in a non-polar solvent (like hexane) increases with size of the alcohol, as the non-polar chain increases. However, as the chain keeps increasing, will the solubility eventually start to drop because the molecule becomes too large?

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    $\begingroup$ Yes, I expect so. $\endgroup$ – Ivan Neretin Mar 2 at 14:20
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    $\begingroup$ Think about the extreme. I wouldn't expect polyethylene to be very soluble in hexane. $\endgroup$ – MaxW Mar 2 at 16:22
  • $\begingroup$ @Max. The problem is related to alcohols, not to alcanes $\endgroup$ – Maurice Mar 2 at 17:08
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    $\begingroup$ @Maurice - The terminal -OH group wouldn't make any significant difference in solubility in hexane between a extremely long alkane and a extremely long n-alcohol. $\endgroup$ – MaxW Mar 2 at 17:16
  • $\begingroup$ Actually, polyethylene is soluble in organic solvents such as toluene, xylene, and mehylene chloride at slightly elevated temperatures. You may have even noticed this if you tried to wash a weigh dish with an organic non-polar solvent. This is an interesting question, but I would infer that the length of the chain would not have a significant effect on the solubility of an alcohol of high chain length. $\endgroup$ – Eli Jones Mar 2 at 18:05

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