Aniline can be separated from phenol using

Options

A. `Na_(2)CO_(3)`
B. `NaNO_(2) + HCl` at `0^(@) C`
C. `NaCl`
D. Acidified `KMnO_(4)`

Explanation

To separate aniline from phenol, we can utilize the difference in their solubility in acidic and basic conditions. Here is a step-by-step solution:

### Step 1: Prepare the Mixture
Start by mixing aniline and phenol in a suitable solvent, such as water or an organic solvent.

**Hint:** Remember that aniline is a basic amine while phenol is a weak acid.

### Step 2: Adjust the pH
Add hydrochloric acid (HCl) to the mixture. This will protonate the aniline, converting it into anilinium chloride, which is soluble in water.

**Hint:** The protonation of aniline increases its solubility in the aqueous phase.

### Step 3: Separate the Phases
After adding HCl, the mixture should be allowed to settle. The anilinium chloride will remain in the aqueous phase, while phenol will remain in the organic phase.

**Hint:** Use a separating funnel to facilitate the separation of the two phases.

### Step 4: Collect the Aqueous Phase
Carefully collect the aqueous phase containing the anilinium chloride. This phase can be further processed to recover aniline.

**Hint:** Be cautious while separating the layers to avoid mixing them again.

### Step 5: Regenerate Aniline
To regenerate aniline from anilinium chloride, add a strong base, such as sodium hydroxide (NaOH), to the aqueous solution. This will deprotonate anilinium chloride back to aniline.

**Hint:** The reaction will shift back to the free base form of aniline, which is less soluble in water.

### Step 6: Isolate Aniline
After the reaction with NaOH, extract the aniline from the aqueous solution using an organic solvent like ether or dichloromethane.

**Hint:** Aniline will be more soluble in the organic solvent than in water.

### Summary
By following these steps, aniline can be effectively separated from phenol using acid-base extraction techniques.

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