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Standard XII

Chemistry

Nucleophilic Substitution in Alkyl Halides

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Question

A solution of m-chloroaniline, m-chlorophenol, m-chlorobenzoic acid in ethyl acetate was extracted initially with a saturated solution of $N a H C O_{3}$ to give fraction A. The leftover organic phase was extracted with dilute $N a O H$ to give fraction B. The final organic layer was labelled as fraction C. Fractions A, B and C, contain respectively:

m-chlorophenol, m-chlorobenzoic acid and m-chloroaniline

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m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline

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m-chloroaniline, m-chlorobenzoic acid and m-chlorophenol

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m-chlorobenzoic acid, m-chloroaniline and m-chlorophenol

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Solution

The correct option is B m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline
m-chlorobenzoic acid being the most acidic can be separated by a weak base like $N a H C O_{3}$ and hence will be labelled fraction A.

m-chlorophenol is not as acidic as m-chlorobenzoic acid, and can be separated by a stronger base like $N a O H$ , and hence can be labelled as fraction B.

m-chloroaniline being a base, does not react with either of the bases and hence would be labelled as fraction C.

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