A solution of m - chloroaniline, m- chlorophenol and m - chlorobenzoinc acid in ethyl acetate was extracted initially with a saturated solution of ` Na HCO _ 3 ` 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 :

Options

A. m - chlorophenol , m - chlorobenzoic acid and m - chloroaniline
B. m - chlorobenzoic acid, m - chloroaniline and m - chlorophenol
C. m - chlorobenzoic acid, m - chlorophenol and m - chloroaniline
D. m - chloroaniline, m - chlorobenzoic acid and m - chlorophenol

Answer

To solve the problem, we need to analyze the extraction process step by step, focusing on the behavior of each compound in the presence of the reagents used.

### Step 1: Identify the Compounds
We have three compounds in the solution:
1. m-Chloroaniline (A)
2. m-Chlorophenol (B)
3. m-Chlorobenzoic acid (C)

### Step 2: Extraction with NaHCO3
The first extraction is done using a saturated solution of sodium bicarbonate (NaHCO3), which is a weak base.

- **Behavior of the Compounds:**
- **m-Chloroaniline (A)**: This is a weak base due to the presence of the amino group (-NH2). It will not react with NaHCO3.
- **m-Chlorophenol (B)**: This is a weak acid. It will not react significantly with NaHCO3.
- **m-Chlorobenzoic acid (C)**: This is a stronger acid compared to phenol. It will react with NaHCO3 to form a sodium salt (sodium m-chlorobenzoate) and will be extracted into the aqueous phase.

**Conclusion for Fraction A**:
- Fraction A contains m-Chlorobenzoic acid (C) as it reacts with NaHCO3.

### Step 3: Extraction with Dilute NaOH
After the first extraction, we have an organic phase left that contains m-Chloroaniline and m-Chlorophenol. This phase is then extracted with dilute sodium hydroxide (NaOH), which is a strong base.

- **Behavior of the Compounds**:
- **m-Chloroaniline (A)**: As a weak base, it will remain in the organic phase and will not react with NaOH.
- **m-Chlorophenol (B)**: This is a weak acid and will react with NaOH to form sodium m-chlorophenoxide, which will be extracted into the aqueous phase.

**Conclusion for Fraction B**:
- Fraction B contains m-Chlorophenol (B) as it reacts with NaOH.

### Step 4: Remaining Organic Layer
After the extraction with NaOH, the remaining organic layer will contain m-Chloroaniline.

**Conclusion for Fraction C**:
- Fraction C contains m-Chloroaniline (A) as it does not react with either NaHCO3 or NaOH.

### Final Summary
- **Fraction A**: m-Chlorobenzoic acid (C)
- **Fraction B**: m-Chlorophenol (B)
- **Fraction C**: m-Chloroaniline (A)

### Final Answer
- Fraction A contains m-Chlorobenzoic acid, Fraction B contains m-Chlorophenol, and Fraction C contains m-Chloroaniline.

---