Identify the nature of each compound

The mixture contains:

• $m$-chlorobenzoic acid: carboxylic acid
• $m$-chlorophenol: phenol (weak acid)
• $m$-chloroaniline: amine (basic)

Extraction with saturated $NaHCO_3$

Sodium bicarbonate is a weak base. It reacts with carboxylic acids but not with phenols.

$\text{ArCOOH} + NaHCO_3 \rightarrow \text{ArCOO}^- Na^+ + CO_2 + H_2O$

Therefore, only $m$-chlorobenzoic acid is converted into its water-soluble sodium salt and goes into the aqueous layer.

So, Fraction A = $m$-chlorobenzoic acid.

Extraction of leftover organic layer with dilute $NaOH$

Now the organic layer contains:

• $m$-chlorophenol
• $m$-chloroaniline

Dilute $NaOH$ is a stronger base than $NaHCO_3$ and deprotonates phenol:

$\text{ArOH} + NaOH \rightarrow \text{ArO}^- Na^+ + H_2O$

Thus $m$-chlorophenol becomes water-soluble sodium phenoxide and goes into the aqueous layer.

So, Fraction B = $m$-chlorophenol.

Final organic layer

The compound left in the organic layer is the neutral/basic compound that was not extracted by base:

• $m$-chloroaniline

So, Fraction C = $m$-chloroaniline.

Match with options

Fractions $A, B, C$ contain respectively:

• $A$: $m$-chlorobenzoic acid
• $B$: $m$-chlorophenol
• $C$: $m$-chloroaniline

This corresponds to Option B.