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A solution of m-chloroaniline, m-chlorophenol and m-chlorobenzoic acid in ethyl acetate was extracted initially with a saturated solution of NaHCO3 to give fraction A. The left over organic phase was extracted with dilute NaOH solution to give fraction B. The final organic layer was labelled as fraction C. Fractions A, B and C, contain respectively:

1. m-chlorobenzoic acid, m-chloroaniline and m-chlorophenol
2. m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline
3. m-chlorophenol, m-chlorobenzoic acid and m-chloroaniline
4. m-chloroaniline, m-chlorobenzoic acid and m-chlorophenol

Correct answer: m-chlorobenzoic acid, m-chlorophenol and m-chloroaniline

Solution

Fraction A contains m-chlorobenzoic acid, which is acidic and soluble in the NaHCO3 solution. Fraction B contains m-chlorophenol, which is a weak acid and can be deprotonated by dilute NaOH, leaving m-chloroaniline, a neutral compound, in the final organic layer (fraction C). Thus, the correct order of fractions is m-chlorobenzoic acid in A, m-chlorophenol in B, and m-chloroaniline in C.

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