The Henderson-Hasselbalch equation is very useful in the laboratory for separating compounds in a mixture. Two compounds; C6H11COOH and C6H11N* H3 dissolved in a mixture of water and diethyl ether. Water and diethyl ether are barely soluble in each other, so they form two layers when combined. Given that C6H11COOH has a pka = 4.8 and C6H11N*H3 has a pka = 10.7. Estimate a. What pH would you make the water layer to cause both compounds to dissolve in it? %3D Justify your answer. b. What pH would you make the water layer to cause the carboxylic acid to dissolve in the ether layer and the amine to dissolve in the water layer? Justify your answer.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter10: Organohalides
Section10.SE: Something Extra
Problem 19MP: The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol...
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i got a answer for the a) is it correct the the pH need to be in pH 1 in order to dissolve both compound in which in acidic solution or charge ion where if it set 4 unit away from pka both compound it will be in acidic solution ? carbonyll will ( 4.8-4=0.8) and amine will (10.7-4=6.7) and different between 2 will be in 5.9 hence if pH =1 so amine will still in acidic rigth? . but for b) it state oposite which origin carbonyl in water while the origin amine in diethyl ether . and the question want the carbonyl in diethyl ether while amin ine water . so what should it do ? is it the pH still 2 unit away like ( pH around 6.8-8.7) how does it work that way ? it still at origin right ? 

The Henderson-Hasselbalch equation is very useful in the laboratory for separating
compounds in a mixture. Two compounds; C6H11COOH and C6H11N* H3 dissolved in a mixture
of water and diethyl ether. Water and diethyl ether are barely soluble in each other, so they
form two layers when combined. Given that C6H11COOH has a pka = 4.8 and C6H11N*H3 has a
pka = 10.7. Estimate
a. What pH would you make the water layer to cause both compounds to dissolve in it?
%3D
Justify your answer.
b. What pH would you make the water layer to cause the carboxylic acid to dissolve in
the ether layer and the amine to dissolve in the water layer? Justify your answer.
Transcribed Image Text:The Henderson-Hasselbalch equation is very useful in the laboratory for separating compounds in a mixture. Two compounds; C6H11COOH and C6H11N* H3 dissolved in a mixture of water and diethyl ether. Water and diethyl ether are barely soluble in each other, so they form two layers when combined. Given that C6H11COOH has a pka = 4.8 and C6H11N*H3 has a pka = 10.7. Estimate a. What pH would you make the water layer to cause both compounds to dissolve in it? %3D Justify your answer. b. What pH would you make the water layer to cause the carboxylic acid to dissolve in the ether layer and the amine to dissolve in the water layer? Justify your answer.
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