Which of the following compound gives benzoic acid on hydrolysis?

Options

A. Chlorobenzene
B. Benzoyl chloride
C. Chlorophenol
D. Chlorotoluene

Answer

To determine which compound gives benzoic acid upon hydrolysis, we will analyze each of the given options step by step.

### Step 1: Identify the compounds
The compounds provided are:
1. Chlorobenzene
2. Benzoyl chloride
3. Chlorophenol
4. Chlorotoluene

### Step 2: Analyze each compound

**Option 1: Chlorobenzene (C6H5Cl)**
- Chlorobenzene has a chlorine atom attached to a benzene ring.
- The carbon-chlorine bond in chlorobenzene has partial double bond character due to resonance, making it resistant to hydrolysis.
- **Conclusion**: Chlorobenzene does not yield benzoic acid upon hydrolysis.

**Option 2: Benzoyl chloride (C6H5COCl)**
- Benzoyl chloride consists of a carbonyl group (C=O) and a chlorine atom attached to the benzene ring.
- Upon hydrolysis, benzoyl chloride reacts with water to form benzoic acid (C6H5COOH) and hydrochloric acid (HCl).
- **Conclusion**: Benzoyl chloride does yield benzoic acid upon hydrolysis.

**Option 3: Chlorophenol (C6H4ClOH)**
- Chlorophenol has a chlorine atom and a hydroxyl group (-OH) attached to the benzene ring.
- Similar to chlorobenzene, the carbon-chlorine bond in chlorophenol also has partial double bond character, which makes it difficult to hydrolyze.
- **Conclusion**: Chlorophenol does not yield benzoic acid upon hydrolysis.

**Option 4: Chlorotoluene (C6H4(CH3)Cl)**
- Chlorotoluene has a chlorine atom and a methyl group (-CH3) attached to the benzene ring.
- The carbon-chlorine bond again has partial double bond character, which prevents hydrolysis.
- **Conclusion**: Chlorotoluene does not yield benzoic acid upon hydrolysis.

### Final Conclusion
The only compound that gives benzoic acid upon hydrolysis is **Benzoyl chloride** (Option 2).

### Summary of the Answer
The correct answer is **Option 2: Benzoyl chloride**.

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