Sunday, November 6, 2011
Why phenol is more soluble in NaOH than in water?
The reason why phenol is more soluble in NaOH than in water is because phenol is slightly acidic. The Ka for phenol in water is 1e-10. Of course, this is not very strong. But by mixing with NaOH, it causes the phenol to release the H+ to form sodium phenoxide. The one negative charge on this compound can move to different locations in the phenol to form different resonances (4 resonances in total) and create very stable compound. Furthermore, the reaction between NaOH and phenol is exothermic, and the equilibrium lies far to the right. This makes the sodium phenoxide extra stable.
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