React Aniline w/ Br2: Mechanism & Desired Product

I think it would be difficult to control the regiochemistry of the reaction.In summary, the conversation discusses the possibility of reacting aniline with Br2 in the presence of CH3CH2OH to obtain a desired product. However, due to the strong activating nature of -NH2, it may be difficult to control the regiochemistry and avoid obtaining unwanted products. It is suggested to follow a different reaction pathway, as shown in the textbook, involving an aldehyde and bromine water. Attempting to write out the mechanism can help in understanding other electrophilic substitutions.
  • #1
SpectraPhy09
25
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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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  • #2
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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Likes SpectraPhy09 and TeethWhitener
  • #3
Can you attempt to write out the mechanism? It’s quite general and will help you to understand other electrophilic substitutions.
 
  • #4
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
 

FAQ: React Aniline w/ Br2: Mechanism & Desired Product

1. What is the purpose of reacting aniline with Br2?

The purpose of this reaction is to introduce a bromine atom onto the benzene ring of aniline, creating a bromoaniline product. This can be useful for further reactions or modifications of the molecule.

2. What is the general mechanism for this reaction?

The general mechanism involves the electrophilic substitution of the bromine atom onto the benzene ring of aniline. The Br2 molecule first dissociates into two Br+ ions, which then attack the electron-rich benzene ring. The resulting intermediate is then deprotonated to form the final product.

3. How does the presence of a Lewis acid catalyst affect the reaction?

A Lewis acid catalyst, such as FeBr3, can increase the rate of the reaction by coordinating with the Br2 and making it more electrophilic. This allows for a faster and more efficient reaction to take place.

4. What factors can influence the selectivity of the reaction?

The selectivity of the reaction can be influenced by steric hindrance and electronic effects. For example, if there are other substituents on the benzene ring, they may affect where the bromine atom will be introduced. Additionally, electron-donating groups can increase the rate of the reaction, while electron-withdrawing groups can decrease it.

5. How can the desired product be isolated and purified?

The desired product, bromoaniline, can be isolated and purified through techniques such as recrystallization, column chromatography, or distillation. These methods can help separate the product from any remaining reactants or byproducts, resulting in a pure sample of the desired product.

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