A mixture of 1 g each of chlorobenzene, aniline, and benzoic acid is dissolved in 50 mL ethyl acetate and placed in a separating funnel. 5 M NaOH (30 mL) was added in the same funnel. The funnel was shaken vigorously and then kept aside. The ethyl acetate layer in the funnel contains :

Practical Organic Chemistry PYQ — JEE Main 2025 · 7 Apr · Shift 2 · Q7 with Solution

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Correct answer: A

Identify the nature of each compound

The mixture contains:
- Chlorobenzene: neutral, non-acidic, non-basic under these conditions
- Aniline: a weak base
- Benzoic acid: an acid
Effect of adding $5\,\text{M}$ NaOH

Sodium hydroxide is a strong base. It will react with the acidic component, benzoic acid.

$\ce{C6H5COOH + NaOH -> C6H5COONa + H2O}$

So benzoic acid is converted into sodium benzoate, which is an ionic salt and prefers the aqueous layer.
Behavior of aniline in basic medium

Aniline is a base:

$\ce{C6H5NH2}$

In the presence of NaOH, there is no acid present to convert it into a water-soluble salt such as anilinium chloride. Therefore, aniline remains in its free base form, which is more soluble in the organic layer (ethyl acetate).
Behavior of chlorobenzene

Chlorobenzene is neutral and does not react with NaOH under these conditions. It remains in the organic layer.
Conclusion about the ethyl acetate layer
- Benzoic acid $\to$ converted to sodium benzoate $\to$ goes to aqueous layer
- Aniline $\to$ remains unreacted free base $\to$ organic layer
- Chlorobenzene $\to$ organic layer
Hence, the ethyl acetate layer contains chlorobenzene and aniline.
Check options
- A: chlorobenzene and aniline $\rightarrow$ correct
- B: benzoic acid and aniline $\rightarrow$ incorrect
- C: benzoic acid $\rightarrow$ incorrect
- D: benzoic acid and chlorobenzene $\rightarrow$ incorrect

Therefore, the correct answer is A.