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Chemistry Question 64 – JEE-MAIN 2025

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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 :

Understand the acid-base properties of each compound and how they interact with the added base.

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Ninja Strategy•Eliminate Reacting Acid

Identify that benzoic acid, being an acid, will react with the strong base NaOH and move to the aqueous layer, eliminating all options containing benzoic acid.

Step 1: Analyze Acid-Base Properties of Compounds✦ Active

Chlorobenzene is a neutral compound. Aniline is a weak base. Benzoic acid is a carboxylic acid, hence acidic.

Step 2: Determine Reactivity with NaOH○ Expand

When 5 M NaOH (a strong base) is added:

1. Chlorobenzene (neutral) will not react with NaOH and will remain in the organic (ethyl acetate) layer.

2. Aniline (weak base) will not react with NaOH and will remain in the organic (ethyl acetate) layer.

3. Benzoic acid (acidic) will react with NaOH to form sodium benzoate, which is an ionic salt.

C6H5COOH+NaOH→C6H5COONa+H2O
💡 Teacher's Secret Hint

Remember that weak bases like aniline do not react with strong bases like NaOH.

Step 3: Identify Components in Ethyl Acetate Layer○ Expand

Sodium benzoate (C6H5COONa) is water-soluble and will move into the aqueous (NaOH) layer. Therefore, benzoic acid will be extracted into the aqueous layer.

Chlorobenzene and aniline, being unreactive with NaOH and soluble in ethyl acetate, will remain in the ethyl acetate (organic) layer.

💡 Teacher's Secret Hint

The ethyl acetate layer is the organic layer, and the NaOH solution forms the aqueous layer. Water-soluble salts will partition into the aqueous layer.

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