Which of the following does not give benzoic acid on hydrolysis?

Options

A. Phenyl cyanide
B. Benzoyl chloride
C. Benzyl chloride
D. Methyl benzoate

Answer

To determine which compound does not yield benzoic acid upon hydrolysis, we will analyze the hydrolysis reactions of the given compounds: phenyl cyanide, benzoyl chloride, benzyl chloride, and methyl benzoate.

### Step-by-Step Solution:

1. **Identify the Compounds**:
- Phenyl cyanide (C6H5C≡N)
- Benzoyl chloride (C6H5C(=O)Cl)
- Benzyl chloride (C6H5CH2Cl)
- Methyl benzoate (C6H5C(=O)OCH3)

2. **Hydrolysis of Phenyl Cyanide**:
- When phenyl cyanide is hydrolyzed, it reacts with water to form benzoic acid (C6H5C(=O)OH) and ammonia (NH3).
- **Reaction**:
\[ C6H5C≡N + H2O \rightarrow C6H5C(=O)OH + NH3 \]
- **Conclusion**: Phenyl cyanide gives benzoic acid.

3. **Hydrolysis of Benzoyl Chloride**:
- Benzoyl chloride reacts with water to form benzoic acid and hydrochloric acid (HCl).
- **Reaction**:
\[ C6H5C(=O)Cl + H2O \rightarrow C6H5C(=O)OH + HCl \]
- **Conclusion**: Benzoyl chloride gives benzoic acid.

4. **Hydrolysis of Benzyl Chloride**:
- Benzyl chloride reacts with water to form benzyl alcohol (C6H5CH2OH) and hydrochloric acid.
- **Reaction**:
\[ C6H5CH2Cl + H2O \rightarrow C6H5CH2OH + HCl \]
- **Conclusion**: Benzyl chloride does NOT give benzoic acid; it gives benzyl alcohol instead.

5. **Hydrolysis of Methyl Benzoate**:
- Methyl benzoate reacts with water to form benzoic acid and methanol (CH3OH).
- **Reaction**:
\[ C6H5C(=O)OCH3 + H2O \rightarrow C6H5C(=O)OH + CH3OH \]
- **Conclusion**: Methyl benzoate gives benzoic acid.

### Final Answer:
Among the given compounds, **benzyl chloride** does not yield benzoic acid upon hydrolysis; instead, it produces benzyl alcohol.

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