The structure of Wheland intermediate obtained after the attack of `Br^(+)` on anilinium ion is:

Options

A.
B.
C.
D.

Answer

To determine the structure of the Wheland intermediate formed after the attack of the bromonium ion on the anilinium ion, we can follow these steps:

### Step 1: Understand the Structure of Anilinium Ion
The anilinium ion is derived from aniline (C6H5NH2) by protonation of the amine group, resulting in a positively charged nitrogen. The structure can be represented as follows:

```
H
|
C6H5-N⁺
```

### Step 2: Identify the Electrophile
In this case, the electrophile is the bromonium ion (Br⁺). This species is generated from bromine (Br2) and acts as a strong electrophile that can attack the anilinium ion.

### Step 3: Determine the Position of Attack
The anilinium ion is a meta-director due to the electron-withdrawing nature of the positively charged nitrogen. Therefore, the bromonium ion will preferentially attack the meta position relative to the nitrogen atom.

### Step 4: Draw the Structure After Bromonium Ion Attack
When the bromonium ion attacks the meta position, it forms a bond with one of the carbon atoms in the aromatic ring. The positive charge from the nitrogen will influence the distribution of charge in the aromatic system.

### Step 5: Delocalization of Positive Charge
After the attack, the positive charge will be delocalized over the aromatic ring, except for the carbon atom that is directly bonded to the bromine. The structure can be represented as follows:

```
Br
|
C6H4-N⁺
/ \
C C
/ \
C C
\ /
C---C
```

In this structure, the positive charge is delocalized across the five carbons adjacent to the bromine atom, while the carbon attached to bromine does not carry a positive charge.

### Final Structure of Wheland Intermediate
The final structure of the Wheland intermediate after the attack of the bromonium ion on the anilinium ion is as follows:

```
Br
|
C6H4-N⁺
/ \
C⁺ C⁺
/ \
C⁺ C⁺
\ /
C---C
```

### Conclusion
The Wheland intermediate is characterized by a delocalized positive charge across the five carbon atoms of the aromatic ring, with the carbon bonded to bromine remaining neutral.