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

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