activators - donate e- and deactivators -w/draw e- ?

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dentalstudent2021

so activators make the ring unstable right since they donate e- ?

and vice versa for deactivators ?

so....since activators donate e- the ring doesnt want e- making it a poor Lewis Acid ?

vice versa for deactivators ?
 
I don't think you're supposed to look at e- donors/acceptors as activators/deactivators unless looking at benzene specifically. I look at it like this, is lewis acid is something that accepts electrons so the more electron accepting is it the stronger the lewis acid aka the more positive charge it has the more likely it will want to accept electrons. So if you have electron withdrawing groups on something it will make it more positive and a stronger lewis acid.

but since you're specifically talking about a ring (i'm assuming benzene) i think you're right. I made this list a while back that helps me remember a little

Electron Donating Groups:
Increase Nucleophile Strength (reactivity)
Increalse Base Strength
Decrease Electrophile strength (reactivity)
Decrease Acid Strength

Electron Withdrawing Groups:
Decrease Nucleophile Strength (reactivity)
Decrease Base Strength
Increase Electrophile strength (reactivity)
Increase Acid Strength
 
so activators make the ring unstable right since they donate e- ?

and vice versa for deactivators ?

so....since activators donate e- the ring doesnt want e- making it a poor Lewis Acid ?

vice versa for deactivators ?

You seem very lost...have a seat. An activating group simply means the molecule is made more reactive. The stability of the molecule is NOT the factor,,,,but reaction rate is........ An activating group such as methoxy, hydroxy or amino simply makes the reaction go FASTER.

The usual mechanism is called Aromatic Electrophilic Substitution, and involves a carbocation intermediate called an Arenium ion. These groups donate electrons and thus STABILIZE the carbocation. Anytime we stabilize the intermediate, the reaction rate INCREASES. A group such as NO2 or COOH will withdraw electrons and therefore DESTABILIZE the carbocationic intermediate and slow the reaction down.

Lewis acids such as FeCl3 and AlCl3 are involved with the mechanism. They allow for the breaking of a carbon-halogen bond or halogen-halogen bond to become more facile. Consult any Organic chemistry book and have a look. For the DAT.....know which groups are activating and which groups are deactivating. I would also understand how to do reactions using these directors.

For example, Cyanobenzene when treated with Chlorine in FeCl3 gives meta isomer product, but the reaction rate is SLOWER.....than if we used Ethylbenzene. Ethylbenzene would have given you a faster rate, and ortho and para isomers mainly.

The Kaplan review book does a nice job to simplify the basics. I also love the Klein book for its clarity and simplicity.

Hope this helps.

Dr. Romano
 
Oh wow didn't really recognize they affect rates as well, but it does make sense for the rates to also be affected! Thanks Dr. Romano!
 
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