Question

You are doing an extraction using water and CHCl3. If the aqueous phase has a pH...

You are doing an extraction using water and CHCl3. If the aqueous phase has a pH of 4.2, which of the following acids will be most effectively extracted into the aqueous phase.

Benzoic acid
Acetic acid
Chloroacetic acid
Hypochlorus acid
They will all be extracted the same
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Answer #1

Correct option: chloroacetic acid

pKa of benzoic acid = 4.20

pKa of acetic acid = 4.75

pKa of chloroacetic acid = 2.87

pKa of hypochlorus acid = 7.53

Now, pH of the aqueous phase = 4.2

Now, if pH < pKa then the acid will not be deprotonated, then it will have significant solublility in chloroform.

And, if pH > pKa then the acid will be deprotonated, then its solubility will decrease in chloroform and it will be extracted into the aqueous phase.

Therefore, chloroacetic acid will be most effectively extracted into the aqueous phase.

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