Above compounds can be differentiated by which of the following chemical test ? (used in decreasing order)

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NaOH, NaHCO₃, HCI

HCl, NaOH, NaHCO₃

NaHCO₃, NaOH, HCl

NaOH, HCl, NaHCO₃

answer is C.

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Detailed Solution

The mixture is composed of a neutral compound m-nitrobenzene, two acids (m-nitrobenzoic acid and m-nitrophenol), and a base (m-nitroaniline). m-nitrobenzoic acid is strong enough as an acid to decompose sodium carbonate; m-nitrophenol is not, but does form a salt with sodium hydroxide. Hence, one way in which a separation may be effected is as follows. Dissolve the mixture in ether (all components are soluble).
(i) Extract the ethereal solution with aqueous sodium carbonate. Only m-nitrobenzoic acid enters the aqueous layer, and may be recovered on acidification.
(ii) Extract the ethereal solution from (i) with aqueous sodium hydroxide. Only m-nitrophenol enters the aqueous layer, and may be recovered on acidification.
(iii) Extract the ethereal solution from (ii) with hydrochloric acid. Only m-nitroaniline enters the aqueous layer, and may be recovered on basifying the solution.
(iv) Evaporate off the ether from the ethereal solution from (iii). This leaves m-nitrobenzene.

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