The pKas of chemicals HX and HY are 5 and 7 respectively. The pKa of carbonic acid H2CO3is 6. If you made up an ether solution of chemicals HX and HY in a separatory funnel, andthen added an aqueous solution of sodium bicarbonate NaHCO3 to that separatory funnel,would both HX and HY stay in the ether layer? Or would either or both of them transfer intothe aqueous layer? If one goes into the water layer, will it be in it’s neutral HX/HY form, or init’s deprotonated anionic form?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.4: Substituent Effects On Acidity
Problem 7P: Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a...
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The pKas of chemicals HX and HY are 5 and 7 respectively. The pKa of carbonic acid H2CO3is 6. If you made up an ether solution of chemicals HX and HY in a separatory funnel, andthen added an aqueous solution of sodium bicarbonate NaHCO3 to that separatory funnel,would both HX and HY stay in the ether layer? Or would either or both of them transfer intothe aqueous layer? If one goes into the water layer, will it be in it’s neutral HX/HY form, or init’s deprotonated anionic form?

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