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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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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