React Aniline w/ Br2: Mechanism & Desired Product

[SpectraPhy09]

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

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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?

 

[Mayhem]

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).

 

[TeethWhitener]

Can you attempt to write out the mechanism? It’s quite general and will help you to understand other electrophilic substitutions.

 

[SpectraPhy09]

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