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An aqueous solution is a mixture of a carboxylic acid (pKa = 4.0) and an amine (pKa of protonated amine = 10.0). To separate the components, the solution at a pH of 2.0 is shaken with diethyl either. On standing, the
  • a)
    top water layer would contain the amine
  • b)
    top ether layer would contain the amine
  • c)
    top water layer would contain the acid
  • d)
    to ether layer would contain the acid
Correct answer is option 'D'. Can you explain this answer?
Most Upvoted Answer
An aqueous solution is a mixture of a carboxylic acid (pKa = 4.0) and ...
Explanation:
When the aqueous solution of carboxylic acid and amine is shaken with diethyl ether at pH 2.0, the following reaction takes place:

RCOOH + RNH2 ↔ RCOO- + RNH3+

At pH 2.0, the carboxylic acid will be predominantly in its protonated form (RCOOH), while the amine will be predominantly in its unprotonated form (RNH2).

The diethyl ether layer will preferentially extract the protonated carboxylic acid (RCOOH) due to its greater solubility in nonpolar solvents, while the unprotonated amine (RNH2) will remain in the aqueous layer.

On standing, the protonated carboxylic acid will transfer its proton to water, forming the uncharged carboxylic acid (RCOOH), which will remain in the diethyl ether layer.

Thus, the diethyl ether layer will contain the carboxylic acid, while the aqueous layer will contain the amine.

Therefore, the correct answer is option D, i.e., the diethyl ether layer would contain the acid.
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An aqueous solution is a mixture of a carboxylic acid (pKa = 4.0) and an amine (pKa of protonated amine = 10.0). To separate the components, the solution at a pH of 2.0 is shaken with diethyl either. On standing, thea) top water layer would contain the amineb) top ether layer would contain the aminec) top water layer would contain the acidd) to ether layer would contain the acidCorrect answer is option 'D'. Can you explain this answer?
Question Description
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