React Aniline w/ Br2: Mechanism & Desired Product

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SUMMARY

The discussion focuses on the reaction of Aniline with Br2 in the presence of CH3CH2OH, exploring the mechanism and potential products. It is established that Aniline's -NH2 group is a strong activating group, leading to challenges in controlling the reaction outcome, which may result in both di- and tribrominated products. The textbook method involves an initial reaction with an aldehyde followed by bromination and acidification to achieve the desired product. Direct bromination of Aniline is discouraged due to the complexity of the resulting mixture of products.

PREREQUISITES
  • Understanding of electrophilic aromatic substitution mechanisms
  • Familiarity with the reactivity of amines in organic chemistry
  • Knowledge of bromination reactions and their conditions
  • Basic concepts of organic synthesis involving aldehydes and alcohols
NEXT STEPS
  • Study the mechanism of electrophilic aromatic substitution in detail
  • Research the effects of activating and deactivating groups on aromatic reactions
  • Learn about the synthesis of brominated aromatic compounds
  • Explore the role of solvents like CH3CH2OH in organic reactions
USEFUL FOR

Chemistry students, organic chemists, and researchers interested in aromatic substitution reactions and the synthesis of brominated compounds.

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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Likes   Reactions: SpectraPhy09 and TeethWhitener
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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