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Question

Which is useful for separating benzoic acid from methyl benzoate?

A
aq.NaHCO3
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B
dil.HCl
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C
aq.NaHSO3
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D
dil.H2SO4
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Solution

The correct option is A aq.NaHCO3

As benzoic acid is an acid it'll react with a NaHCO3, which is a base and become benzoate, which is negatively charged. As. charged species are soluble in water and other polar solvents but not in non-polar compounds. Thus, this can be used to seperate benzoic acid from methly benzoate.

Add to the mixture, NaHCO3. This should convert all of the benzoic acid into benzoate, which will then dissolve readily in the aqueous base solution. Mix it around a bit to ensure that all the benzoic acid is dissolved, then let it settle until the aqueous layer and the organic layer are separated . The top layer is the aqueous layer, because water is less dense than methyl benzoate. From here, simply remove the aqueous layer with a pipette and be left with a much more pure methyl benzoate solution. You can repeat the washing 2-3 times to be sure, or until you no longer observe an acid-base reaction (bubbling) when you add base


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