Which represents nucleophilic aromatic substitution reaction ?

Options

A. Reaction of benzene with `Cl_(2)` in sunlight
B. Benzyl bromide hydrolysis with water
C. Reaction of NaOH with dinitrofluoro benzene
D. Sulphonation of benzene

Explanation

To determine which reaction represents a nucleophilic aromatic substitution, we need to analyze the options provided and identify the one that fits the criteria for this type of reaction.

### Step-by-Step Solution:

1. **Understanding Nucleophilic Aromatic Substitution**:
- Nucleophilic aromatic substitution occurs when a nucleophile attacks an aromatic ring that has an electron-withdrawing group (EWG) attached. This reaction typically involves the substitution of a leaving group (like a halogen) on the aromatic ring.

2. **Analyzing the Options**:
- **Option A**: Reaction of benzene with Cl2 in sunlight.
- This is an electrophilic substitution reaction (halogenation) and does not involve nucleophilic substitution. **(Incorrect)**

- **Option B**: Benzyl bromide hydrolysis with water.
- Benzyl bromide (C6H5-CH2Br) undergoes hydrolysis, which involves the substitution of the bromine atom with an OH group, but it is not an aromatic substitution since the substitution occurs on the aliphatic carbon (CH2) and not on the aromatic ring. **(Incorrect)**

- **Option C**: Reaction of NaOH with dinitrofluorobenzene.
- Dinitrofluorobenzene has two nitro groups (which are strong electron-withdrawing groups) attached to the aromatic ring. The presence of these groups enhances the nucleophilic substitution reaction. Here, the hydroxide ion (OH-) acts as the nucleophile and attacks the carbon atom bonded to the fluorine, leading to the substitution of fluorine with OH. This is a classic example of nucleophilic aromatic substitution. **(Correct)**

- **Option D**: Sulfonation of benzene.
- This is an electrophilic substitution reaction where sulfur trioxide (SO3) or sulfuric acid (H2SO4) introduces a sulfonyl group (-SO3H) into the aromatic ring. **(Incorrect)**

3. **Conclusion**:
- The reaction that represents nucleophilic aromatic substitution is **Option C: Reaction of NaOH with dinitrofluorobenzene**.