You have a solution of benzoic acid in diethyl ether (d = 0.7) along with other
ID: 885961 • Letter: Y
Question
You have a solution of benzoic acid in diethyl ether (d = 0.7) along with other unknown neutral compounds. You treat the solution with 1M HCl and isolate the aqueous layer. But neutralization and basification with 4M NaOH fails to produce pure benzoic acid. Why? What could be done instead to isolate the desired compound?I m having a really hard time understanding why this wouldn t work, and the teacher never told us any other options.
Can you please explain this as simply as you can? Thanks You have a solution of benzoic acid in diethyl ether (d = 0.7) along with other unknown neutral compounds. You treat the solution with 1M HCl and isolate the aqueous layer. But neutralization and basification with 4M NaOH fails to produce pure benzoic acid. Why? What could be done instead to isolate the desired compound?
I m having a really hard time understanding why this wouldn t work, and the teacher never told us any other options.
Can you please explain this as simply as you can? Thanks You have a solution of benzoic acid in diethyl ether (d = 0.7) along with other unknown neutral compounds. You treat the solution with 1M HCl and isolate the aqueous layer. But neutralization and basification with 4M NaOH fails to produce pure benzoic acid. Why? What could be done instead to isolate the desired compound?
I m having a really hard time understanding why this wouldn t work, and the teacher never told us any other options.
Can you please explain this as simply as you can? Thanks
Explanation / Answer
Generally a mixture of benzoic acid and a neutral compound is separated by an acid-base extraction. The benzoic acid is a carboxylic acid that soluble in ether and insoluble in water.
When the NaOH, a strong base is added to the mixture, it reacts with both HCl and benzoic acid and forms a sodium benzoate salt along with sodium chloride salt. These two salts are soluble in water (aqueous medium) and insoluble in ether (organic layer).
Therefore, if we separate the aqueous layer, the sodium benzoate along with sodium chloride is extracted. Thus pure benzoic acid could not be separated.
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