Reaction of `C_6H_5CH_2Br` with aqueous sodium hydroxide follows........

Options

A. `SN^(1)` mechanism
B. `SN^(2)` mechanism
C. Any of the above two depending upon the temperature of reaction
D. Saytzeff rule

Explanation

To solve the question regarding the reaction of `C6H5CH2Br` (benzyl bromide) with aqueous sodium hydroxide (NaOH), we need to analyze the reaction mechanism involved.

### Step-by-Step Solution:

1. **Identify the Reactant and Conditions**:
- The reactant is `C6H5CH2Br`, which is benzyl bromide.
- The reagent is aqueous sodium hydroxide (NaOH), which provides hydroxide ions (OH⁻).

2. **Determine the Type of Reaction**:
- The reaction can be classified as a nucleophilic substitution reaction, which can proceed via either the SN1 or SN2 mechanism.

3. **Analyze the Structure of Benzyl Bromide**:
- Benzyl bromide has a benzyl group (`C6H5CH2-`) attached to a bromine atom. The carbon atom bonded to the bromine is a primary carbon.

4. **Consider the Mechanism**:
- **SN1 Mechanism**: This mechanism involves the formation of a carbocation intermediate. For this to occur, the leaving group (Br⁻) must depart, forming a carbocation. The stability of the carbocation is crucial; benzyl carbocations are resonance-stabilized due to the adjacent aromatic ring.
- **SN2 Mechanism**: This mechanism involves a direct attack by the nucleophile (OH⁻) on the carbon atom bonded to the leaving group (Br⁻), occurring in one concerted step.

5. **Evaluate Carbocation Stability**:
- In the case of benzyl bromide, when Br⁻ leaves, it forms a benzyl carbocation (`C6H5CH2⁺`). This carbocation is resonance-stabilized because the positive charge can be delocalized onto the aromatic ring, making it relatively stable.

6. **Nucleophilic Attack**:
- Once the carbocation is formed, the hydroxide ion (OH⁻) from the aqueous NaOH can attack the positively charged carbon atom, leading to the formation of benzyl alcohol (`C6H5CH2OH`).

7. **Conclusion**:
- Given the stability of the resonance-stabilized carbocation and the nature of the reactant, the reaction of `C6H5CH2Br` with aqueous NaOH follows the SN1 mechanism.

### Final Answer:
The reaction of `C6H5CH2Br` with aqueous sodium hydroxide follows the SN1 mechanism.

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