Toluene reacts with excess of `CI_(2)` in presence of sunlight to give a product which on hydrolysis followed by reaction with `NaOH` gives .

Options

A. .
B. .
C. .
D. None of these

Explanation

To solve the problem step by step, we will analyze the reaction of toluene with chlorine in the presence of sunlight, followed by hydrolysis and reaction with sodium hydroxide (NaOH).

### Step 1: Identify the Reactants
The reactant is **toluene**, which has the structure of a benzene ring with a methyl group (−CH₃) attached to it.

### Step 2: Reaction of Toluene with Chlorine
When toluene reacts with excess chlorine (Cl₂) in the presence of sunlight, a substitution reaction occurs. The chlorine replaces hydrogen atoms on the toluene molecule. The reaction can be summarized as follows:

1. **First Chlorination**:
\[ \text{C}_6\text{H}_5\text{CH}_3 + \text{Cl}_2 \xrightarrow{\text{sunlight}} \text{C}_6\text{H}_4\text{Cl}\text{CH}_3 + \text{HCl} \]
This results in the formation of **chlorotoluene** (C₆H₄ClCH₃).

2. **Further Chlorination**:
Continuing the chlorination process, we can replace more hydrogen atoms:
\[ \text{C}_6\text{H}_4\text{Cl}\text{CH}_3 + \text{Cl}_2 \xrightarrow{\text{sunlight}} \text{C}_6\text{H}_3\text{Cl}_2\text{CH}_3 + \text{HCl} \]
This can continue until all hydrogen atoms on the methyl group are replaced, leading to **trichloromethylbenzene** (C₆H₂Cl₃CH₃ or CCl₃).

### Step 3: Hydrolysis of the Chlorinated Product
The chlorinated product can be hydrolyzed. The reaction with water (hydrolysis) will replace the chlorine atoms with hydroxyl groups (−OH):

\[ \text{C}_6\text{H}_3\text{Cl}_3\text{CH}_3 + \text{H}_2\text{O} \rightarrow \text{C}_6\text{H}_3\text{(OH)}_3\text{CH}_3 + \text{HCl} \]

### Step 4: Reaction with Sodium Hydroxide (NaOH)
When the hydrolyzed product is treated with sodium hydroxide (NaOH), it leads to the formation of sodium salts of the corresponding acids. The hydroxyl groups can further react with NaOH:

\[ \text{C}_6\text{H}_3\text{(OH)}_3\text{CH}_3 + 3 \text{NaOH} \rightarrow \text{C}_6\text{H}_3\text{(O}^- \text{Na)}_3\text{CH}_3 + 3 \text{H}_2\text{O} \]

### Step 5: Formation of Benzoic Acid
The unstable product formed can lose water (dehydration) to yield **benzoic acid** (C₆H₅COOH):

\[ \text{C}_6\text{H}_3\text{(OH)}_3\text{CH}_3 \rightarrow \text{C}_6\text{H}_5\text{COOH} + \text{H}_2\text{O} \]

### Final Product
The final product formed after these reactions is **sodium benzoate** (the sodium salt of benzoic acid).

### Summary of the Reaction Steps:
1. Toluene reacts with Cl₂ in sunlight to form chlorinated toluene.
2. Hydrolysis of chlorinated toluene replaces Cl with OH groups.
3. Reaction with NaOH forms sodium salts.
4. Dehydration leads to the formation of benzoic acid.