React Aniline w/ Br2: Mechanism & Desired Product

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Discussion Overview

The discussion revolves around the reaction of aniline with bromine (Br2) in the presence of ethanol (CH3CH2OH). Participants explore the mechanism of this reaction and question whether it can yield the desired product directly, contrasting it with a textbook method that involves an initial reaction with an aldehyde.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • One participant expresses uncertainty about the mechanism of the reaction between aniline and Br2, questioning if the direct reaction will yield the desired product.
  • Another participant notes that the -NH2 group is strongly activating, which may lead to difficulties in controlling the products, potentially resulting in both di- and tribrominated products rather than just a mixture of monobrominated ortho- and para- products.
  • Some participants request a mechanism to be written out, suggesting that understanding this general mechanism could aid in comprehending other electrophilic substitutions.

Areas of Agreement / Disagreement

Participants do not reach a consensus on whether the direct reaction of aniline with Br2 will yield the desired product, and there are competing views regarding the control of product formation.

Contextual Notes

There are limitations regarding the assumptions made about the reaction conditions and the potential for multiple products due to the activating nature of the -NH2 group. The discussion does not resolve the mechanism or the effectiveness of the direct reaction.

SpectraPhy09
Messages
23
Reaction score
3
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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