`S_(N)1` characteristics would be exhibited in the hydrolysis of

Options

A. chlorobenzene
B. 1-chloronapthalne
C. propenly chloride
D. 2-chloro-1-propene

Answer

To determine which compound exhibits \( S_N1 \) characteristics during hydrolysis, we need to analyze the stability of the carbocation intermediate formed during the reaction. The \( S_N1 \) mechanism involves two main steps: the formation of a carbocation and then the nucleophilic attack.

### Step-by-Step Solution:

1. **Understanding \( S_N1 \) Mechanism**:
- The \( S_N1 \) (Substitution Nucleophilic Unimolecular) mechanism involves the formation of a carbocation intermediate. The rate of the reaction depends only on the concentration of the substrate.

2. **Identify the Substrate**:
- The question mentions "hydrolysis of propanil chloride". We need to analyze this compound to see if it can form a stable carbocation.

3. **Formation of Carbocation**:
- When propanil chloride undergoes hydrolysis, it first loses the chloride ion (leaving group), forming a carbocation. The structure of propanil chloride can be represented as:
\[ \text{CH}_3\text{C(Cl)=C}(\text{CH}_3)\text{CO} - \text{Cl} \]
- Upon losing the chloride ion, a carbocation is formed:
\[ \text{CH}_3\text{C}^+(\text{CH}_3)\text{CO} \]

4. **Stability of the Carbocation**:
- The stability of the carbocation is crucial for \( S_N1 \) reactions. Tertiary carbocations are more stable than secondary or primary ones due to hyperconjugation and inductive effects.
- In this case, the carbocation formed is a tertiary carbocation, which is stabilized by the surrounding alkyl groups.

5. **Resonance Stabilization**:
- The carbocation can also be stabilized by resonance. The presence of adjacent double bonds or lone pairs can delocalize the positive charge, further stabilizing the carbocation.

6. **Conclusion**:
- Since propanil chloride can form a stable tertiary carbocation through resonance and hyperconjugation, it exhibits \( S_N1 \) characteristics during hydrolysis.

### Final Answer:
The hydrolysis of propanil chloride exhibits \( S_N1 \) characteristics due to the formation of a stable carbocation intermediate.