Amines, organic conversion question

I have 2 questions:
i) What's the mechanism from the 2nd to the 3rd step
ii) From the 4th to 5th step, how did SO3H somehow get deleted and Br end up on ortho instead of para

iTeachChem Helper•3/18/25, 1:53 PM

@Dexter

iTeachChem Helper•3/18/25, 1:53 PM

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stormycloud•3/18/25, 2:52 PM

1) on heating so3h is attached at para
2) this is a common method to get bromine substituted at ortho/para
the so3h dead teases the electron density in benzene which favours the substitution of bromine

stormycloud•3/18/25, 2:55 PM

Actually for the second one, treating the amide with so3h is commonly used when u want to substitute no2 at o and p, but it also can be used for bromine

stormycloud•3/18/25, 2:56 PM

Because when amine is treated with no2 it has a very low yield of nitroproduct

stormycloud•3/18/25, 2:56 PM

Hope this explains it

NNimboi I have 2 questions: i) What's the mechanism from the 2nd to the 3rd step ii) Fro...

Real potato•3/20/25, 5:52 PM

Phele karaya sulphonation to block para position fir karaya ac2o se rxn taki ring thodi kam activate ho then Br2 heat krne se Bromine laga ortho par and So3H islie hata kyuki Heat krne pe SO2 gas nikal jati hai so accordingto le chatelier principal rxn forward direction me favour hoti or last step me Naoh dala taki Amine wapis se ban jae Ac2O hat jayega

NNimboi I have 2 questions: i) What's the mechanism from the 2nd to the 3rd step ii) Fro...

Dexter•3/20/25, 6:21 PM

4-5 is Bromodesulphonation
it is an ipso substitution that was asked in advance a few times

Dexter•3/20/25, 6:21 PM

wow

Dexter•3/20/25, 6:21 PM

mains asked Bromodesulphonation

Dexter•3/20/25, 6:21 PM

a similar reaction is bromodecarboxylation

Dexter•3/20/25, 6:22 PM

same stuff jus sulphonic acid ki jagah carboxylic acid rehta hai

NimboiOP•3/22/25, 1:51 PM

ah yep, got it

NimboiOP•3/22/25, 1:51 PM

thanks guys

NimboiOP•3/22/25, 1:51 PM

+solved _zbro Dexter jee2025.

iTeachChem Helper•3/22/25, 1:51 PM

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Amines, organic conversion question

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