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

### Related Formula textPh-COOH + textNaOH ightarrow textPh-COO^-textNa^+ text (Water soluble salt) [cite: 884, 885]$$\text{Ph-COOH} + \text{NaOH} ightarrow \text{Ph-COO}^-\text{Na}^+ \text{ (Water soluble salt)} [cite: 884, 885]$$ ### Core Logic When aqueous textNaOH$\text{NaOH}$ is added to the mixture: 1. Benzoic acid (textPh-COOH$\text{Ph-COOH}$) reacts to form sodium benzoate (textPh-COONa$\text{Ph-COONa}$), which is highly water-soluble and moves completely into the aqueous layer. 2. Chlorobenzene (textPh-Cl$\text{Ph-Cl}$) and aniline (textPh-NH_2$\text{Ph-NH}_2$) are organic compounds that do not react with aqueous textNaOH$\text{NaOH}$ under normal conditions. Therefore, they remain unreacted in the organic layer (ethyl acetate). ### Step 1: Visual Reaction Progress The separation steps can be visualized tracking the structural components:

Thus, the ethyl acetate layer strictly contains chlorobenzene and aniline. ### Pattern Recognition Acid-base separation shortcut: Strong bases (textNaOH$\text{NaOH}$) pull organic acids into the aqueous phase as salts. Neutral compounds and basic amines stay behind in the organic layer unless a strong acid is added. ### Evaluation Rubric / Model Answer null ### Chapter Mix Class 11 Chemistry: Organic Chemistry - Some Basic Principles and Techniques Class 12 Chemistry: Aldehydes, Ketones and Carboxylic Acids