If I wanted to separate a mixture containing formic acid and naphthol that were dissolved in diethyl ether using acid base extraction. Will I be successful in isolating the two compounds?  Give detailed answer and explanation as to why or why not. Assume the student could use NaHCO3, NAOH or HCl as needed.

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
Chapter23: Amines
Section: Chapter Questions
Problem 23.32P: Suppose you have a mixture of these three compounds. Devise a chemical procedure based on their...
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If I wanted to separate a mixture containing formic acid and naphthol that were dissolved in diethyl ether using acid base extraction. Will I be successful in isolating the two compounds?  Give detailed answer and explanation as to why or why not. Assume the student could use NaHCO3, NAOH or HCl as needed. 

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Both formic acid and naphthol are acidic in nature but pKa value of formic acid is 3.75 and pKa value of naphthol is 9.5. Thus naphthol is a weaker acid as compared to formic acid.

Therefore acid base extraction can be used for their separation.

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