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Question

A mixture contains 4−methylaniline, 2−naphthol, 3−chlorobenzoic acid and 1,3−dinitrobenzene.
The following scheme of separation is used to separate its constituents.
The correct statement(s) regarding the separation method is/are:

884435_f8e1807c15d7478884074b6c5c5f2c89.jpg

A
the reagents in Step 2 and Step 3 can be interchanged (i.e. aq.NaOH in Step 2 and eq.NaHCO3 in Step 3)
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B
Y in $3-chlorobenzoic acid
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C
W and Z are 4methylaniline and 1,3dinitrobenzene respectively
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D
if the original mixture also contains 4 aminobenzoic acid, it will be present in the filtrate of Step 1.
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Solution

The correct options are
C W and Z are 4methylaniline and 1,3dinitrobenzene respectively
D if the original mixture also contains 4 aminobenzoic acid, it will be present in the filtrate of Step 1.
W is water-insoluble 4−methylaniline, a base. It reacts with aq HCl to form hydrochloride salt which is water soluble and goes into the filtrate. Neutralization with aq NaOH regenerates free base 4−methylaniline.
Z is 1,3−dinitrobenzene, a neutral compound. Hence, it neither dissolves in aq. HCl, nor in aq. NaHCO3, nor in aq. NaOH and is found in a final residue.
If the original mixture also contains 4 aminobenzoic acid, it will be present in the filtrate of Step 1.
4 aminobenzoic acid will react with aq. HCl to form hydrochloride salt which is water soluble and goes into the filtrate.

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