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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kateoik on March 29, 2017, 12:49:24 PM

Title: Electrophilic aromatic substitution
Post by: kateoik on March 29, 2017, 12:49:24 PM

Two deactivates group like CN and CHO in position 1,4 what product will give me in an aromatic sulfonation?

Title: Re: Electrophilic aromatic substitution
Post by: wildfyr on March 29, 2017, 10:32:10 PM

Is this hypothetical? Because such a deactivated ring will probably take some serious cooking in real life to sulfonate, and those functional groups could fall apart under such conditions.

What is your first thought?

Title: Re: Electrophilic aromatic substitution
Post by: kateoik on March 30, 2017, 10:54:02 AM

It's an exercise that my professor gave me. Hai thought that I will have an electrophilic substitution that will go in position metà respect to CHO because CHO it's a little bit more reactive than CN. But I have to proof why it forms this product with the resonance formes. The formes are 4 in bought cases and the positive charge goes in bought groups. I don't know if I did well but I am desperate I can't find nothing similar on the internet

Title: Re: Electrophilic aromatic substitution
Post by: kateoik on March 30, 2017, 11:00:53 AM

Both cases and both groups.... sorry for the English

Title: Re: Electrophilic aromatic substitution
Post by: wildfyr on March 30, 2017, 02:52:48 PM

This should help (Thanks Dan!) http://pubs.acs.org/doi/abs/10.1021/cr00002a004

Title: Re: Electrophilic aromatic substitution
Post by: kateoik on March 30, 2017, 03:32:47 PM

Thanks