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12 grade chemistry others

Acetanilide when treated with bromine in acetic acid mainly gives:A. o-BromoacetanilidaB. N-BromoacetanilideC. p-BromoacetanilideD. m-Bromoacetanilide

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1 Year agoGrade
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1 Answer

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1 Year ago

To determine the product formed when acetanilide is treated with bromine in acetic acid, let's analyze the reaction mechanism and the influence of the functional groups present in acetanilide.

### Structure of Acetanilide

Acetanilide is an amide with the following structure:

\[
\text{C}_6\text{H}_5\text{-NH-CO-CH}_3
\]

In this structure:
- The **acetyl group** (–COCH₃) is electron-withdrawing due to the presence of the carbonyl (C=O) group.
- The **aniline moiety** (C₆H₅NH₂) can undergo electrophilic aromatic substitution because the nitrogen atom has a lone pair of electrons that can donate to the aromatic ring, making it more reactive towards electrophiles.

### Bromination in Acetic Acid

When bromine (Br₂) is added to a solution of acetanilide in acetic acid, bromination occurs primarily at the aromatic ring. The key points to consider are:

1. **Directing Effects of the Amine Group**:
- The amine group (–NH₂) is a **strongly activating group** that directs electrophilic substitution to the ortho (o) and para (p) positions of the aromatic ring due to its ability to donate electron density.
- The carbonyl group (C=O) in the acetanilide is a **deactivating group** that will slightly influence the position of bromination but does not significantly overpower the activation of the ring by the amine group.

2. **Position of Bromination**:
- Because of the electron-donating character of the amine group, bromination will predominantly occur at the **ortho** and **para** positions relative to the amine.
- The ortho position is generally favored due to steric hindrance, as the nitrogen atom is already adjacent to the ring.

### Conclusion

Considering these factors, the main product formed from the bromination of acetanilide in acetic acid is **o-bromoacetanilide**.

Thus, the correct answer is:

**A. o-Bromoacetanilide**