Why is water a good choice of solvent for a phenol but not a dialkyl ether?
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Doing a Williamson Ether Synthesis in organic chem. I'm trying to find the relationship between the pKa of a molecule and the choice of solvent in this reaction. We started with cresol.. added KOH and water..... ultimately made a methylphenoxyacetic acid. The pKa of a phenol is approx 10... whereas the pKa of something like ethanol likes around 16. What is "special" about the phneol pKa and the choice of solvent as water? And why would this solvent not be appropriate for preparing a di-alkyl ether? Thanks for all your help Nikki
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Answer:
Phenols are much more acidic than aliphatic alcohols because the phenyl ring is able to delocalize the negative charge. Ionic compounds are (usually) nicely soluble in water, and not in non-polar solvents. Hence, potassium 4-methoxyphenoxide is soluble in water.
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