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 :

Ethyl acetate is an organic solvent that is immiscible with water, so two separate layers form in a separating funnel.
The upper layer (lower density) is ethyl acetate, while the lower layer (higher density) is the aqueous solution of $$5 \text{ M } NaOH$$.

1. Behaviour of benzoic acid:
Benzoic acid is a carboxylic acid. In the presence of the strong base $$NaOH$$ it undergoes neutralisation: $$C_6H_5COOH + NaOH \rightarrow C_6H_5COONa + H_2O$$.
Sodium benzoate $$\left(C_6H_5COONa\right)$$ is an ionic salt, highly soluble in water and almost insoluble in ethyl acetate. Hence benzoic acid transfers completely to the aqueous layer as its salt.

2. Behaviour of aniline:
Aniline is a weak base. In strongly basic medium ($$5 \text{ M } NaOH$$) it remains in the free-base (neutral) form $$C_6H_5NH_2$$ because there is no proton source to convert it to the water-soluble ammonium ion $$C_6H_5NH_3^+$$. Neutral aniline is only sparingly soluble in water but is quite soluble in an organic solvent such as ethyl acetate. Therefore aniline stays in the ethyl acetate layer.

3. Behaviour of chlorobenzene:
Chlorobenzene is a non-polar, neutral molecule. It does not react with $$NaOH$$ under these conditions and is insoluble in water. Thus chlorobenzene also remains in the ethyl acetate layer.

Final distribution:
• Aqueous (lower) layer : sodium benzoate (from benzoic acid) and excess $$NaOH$$.
• Organic (upper ethyl acetate) layer : chlorobenzene + aniline.

Hence the ethyl acetate layer contains chlorobenzene and aniline.
Correct Option D: chlorobenzene and aniline.