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EDG AND EWG
Daniela_5535
#1 Posted : Friday, July 03, 2020 7:39:23 PM
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Hello,

I just wanted to clarify the difference between these two (electron donating and withdrawing), would we also consider electro donating groups to be bases and electron withdrawing groups to be acids ?

Thanks!
INSTR_Katerina_102
#2 Posted : Saturday, July 04, 2020 2:02:59 AM
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This is kind of a more advanced concept.

Electron donating groups (EDG) and electron withdrawing groups (EWG) often modify acid and base strength, but are not themselves acids or bases. They also can stabilize or destabilize an acid or base depending on the charge of the conjugate created.

For example, https://ibb.co/NChSRgS.

I often like to tie it in with Coloumb's law for physics, it's a pretty similar concept.

(+) charge generated from an EWG can stabilize (-) charge on a conjugate base, but (+) charge generated from an EWG can destabilize (+) charge on a conjugate acid. This can change depending on what your acids and bases are, as some conjugate acids and bases are neutral, so you can have opposite effects too.

Please let me know if this is unclear.
Daniela_5535
#3 Posted : Friday, July 10, 2020 6:00:44 PM
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Hello,

I’m still a little confused on the concept, why does the EWG make the amine less basic ? But make the phenol more acidic? I’m just confused on the reading as to why it becomes less or more basic or acidic
INSTR_Molly_59
#4 Posted : Saturday, July 11, 2020 6:10:13 PM
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Hey Daniela,

Less basic, and more acidic, is two sides of the same coin. If something is less basic, its going to be more acidic.

So therefore, the presence of an EWG within a molecule will pull electron density towards itself. In doing so, it will make a compound less of a good base (which usually has lots of electron density to accept more protons), and more acidic (which usually has a lack of electron density).

I hope this helps, please don't hesitate to reply if you are still confused.

Cheers, and happy studying! :)
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