Practicing Success

Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Amines

Question:

The amino group is ortho, para directing and powerful activating substituent so that aryl amines undergo the typical electrophilic substitution reactions readily. In fact, the rate of these reactions is so great that in certain cases poly-substitution, rather than mono-substitution occurs, even under mild conditions. If the reactions in such cases have have to be arrested at the mono-substitution stage, the activating influence of the –NH2 group has to be arrested.

Identify the product of the given reaction. 

Options:

2-Bromoaniline 

4-Bromoaniline 

2,4-Dibromoaniline 

2,4,6-Tribromoaniline 

Correct Answer:

2,4,6-Tribromoaniline 

Explanation:

The correct answer is option 4. 2,4,6-Tribromoaniline.

When aniline \((C_6H_5NH_2)\) reacts with bromine water, it undergoes electrophilic aromatic substitution, leading to the formation of a tribromoaniline. The amino group \((NH_2)\) in aniline is a strong activating group, which makes the aromatic ring highly reactive towards electrophilic bromination. This results in substitution occurring at the ortho and para positions relative to the amino group. The reaction with bromine water (\(Br_2\) in water) proceeds rapidly and does not stop at monosubstitution. Instead, it typically results in the formation of 2,4,6-tribromoaniline due to the high reactivity of the aniline towards bromination. Here is the reaction: