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Topic: Methyl orange Syntehsis lab question!  (Read 1544 times)

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Offline sharbeldam

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Methyl orange Syntehsis lab question!
« on: January 08, 2023, 05:11:33 AM »
In the lab where we react Sulfanilic acid with N,N-dimethylaniline (ofcourse with other reagents).
after we create the diazonium ion, we dissolve the N,N-dimethylaniline with glacial acetic acid to PROTONATE it so it can becomes soluble in aqueous solution, but since the amine became positively charged, we now should get the META product not the PARA, why do we still get the para even though we protonated it?
and is there another goal of glacial acetic acid in addition to making it soluble? i read in some article that it makes it a better electrophile too.
« Last Edit: January 08, 2023, 06:41:33 AM by sharbeldam »
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Offline rolnor

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Re: Methyl orange Syntehsis lab question!
« Reply #1 on: January 30, 2023, 07:39:29 PM »
I dont think the meta-position will be attacked? Its not enough activated? Do you have a reference? Also acetic acid is not strong enough to completely protonate the dimethyl anniline so you still get attack att para.

Offline rolnor

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Re: Methyl orange Syntehsis lab question!
« Reply #2 on: January 30, 2023, 07:45:42 PM »
From what I can se on the net, alkaline conditions are normally used, not acidic. Dimethyl anilline is water soluble as base.

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