Phenols are less acidic than carboxylic acids, with values of pKa around 10. Phenols aredeprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three purecompounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
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Phenols are less acidic than carboxylic acids, with values of pKa around 10. Phenols are
deprotonated by (and therefore soluble in) solutions of sodium hydroxide but not by solutions of sodium bicarbonate. Explain how you would use extractions to isolate the three pure
compounds from a mixture of p-cresol (p-methylphenol), cyclohexanone, and benzoic acid.

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