Chemistry React Aniline w/ Br2: Mechanism & Desired Product

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Reacting aniline with Br2 in the presence of CH3CH2OH raises concerns about controlling the reaction products due to the strong activating nature of the -NH2 group, which can lead to multiple bromination. The textbook method involves first reacting aniline with an aldehyde before introducing bromine water and H+, which helps in achieving the desired product more selectively. Directly using Br2 water could result in a mixture of di- and tribrominated products, complicating the outcome. Understanding the mechanism of electrophilic substitution is crucial for predicting the reaction behavior of aniline. Attempting to outline this mechanism will enhance comprehension of similar reactions.
SpectraPhy09
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Homework Statement
How can we form o-bromo-Aniline or p-bromo-aniline is using anilne?
also, Give structures of intermediate? You can use any reagent.
Relevant Equations
.
I was thinking to react Aniline with Br2 in presence of Ch3ch2-Oh But I don't know the mechanism also I'm confuse will this really give the desired product
In my textbook, they reacted aniline first with an aldehyde and then with bromine water, and then with H+ to get Desired product ..
I want to ask can't we directly react aniline with Br2 water?
 
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An explanation would be that -NH2 is strongly activating, and therefore it would difficult to control which products you get (fx you could get both di- and tribrominated products, not just a mixture of monobrominated o- and p- products).
 
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Can you attempt to write out the mechanism? It’s quite general and will help you to understand other electrophilic substitutions.
 
TeethWhitener said:
Can you attempt to write out the mechanism? It’s quite general and will help you to understand other electrophilic substitutions.
Yes I'll definitely try
 

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