How can O- and COO- act as an electron releasing group in a π system?

In summary, an electron releasing group (ERG) is a functional group that donates electron density to a molecule or π system, increasing its stability. O- and COO- can act as ERGs by donating their lone pair of electrons to the π system. This leads to an increase in electron density and stability of the molecule, which can impact its reactivity and physical properties. The ERG ability of O- and COO- can be affected by neighboring functional groups, with electron-withdrawing groups decreasing their ability and electron-donating groups enhancing it.
  • #1
Frigus
337
160
can anyone explain me how O negative and COO negative acts as electron releasing group,I understood how alkyl groups acts as electron releasing group but I can't understand this
 
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  • #2
Are you referring to activation/deactivation of aromatics? It might help to write out the possible resonance structures. At any rate, for both species, there is a large electron density on the functional group that can form a somewhat continuous connection with the conjugated pi system of the aromatic group.
 
  • #3
Through resonance of the pi orbitals. Sometimes resonance is more important than electronegativity.
 

1. How do O- and COO- act as electron releasing groups in a π system?

O- and COO- are both electron donating groups due to their negative charge. In a π system, these groups can donate electrons through resonance, where the negative charge is delocalized and spread out over the entire molecule. This results in an increase in electron density in the π system, making it more nucleophilic and reactive.

2. What is the mechanism behind O- and COO- acting as electron releasing groups in a π system?

The mechanism involves the lone pair of electrons on the oxygen atom or the carboxylate group being delocalized into the π system through resonance. This increases the electron density in the π system, making it more electron-rich and therefore more reactive.

3. How do O- and COO- affect the stability of a π system?

O- and COO- can increase the stability of a π system by delocalizing the negative charge and spreading it out over the molecule. This results in a more stable and lower energy state for the system.

4. Can O- and COO- act as both electron donating and withdrawing groups in a π system?

Yes, O- and COO- can act as both electron donating and withdrawing groups in a π system depending on the substituents attached to them. For example, if there are electron-withdrawing groups attached to the O- or COO- group, they can withdraw electrons through resonance, making them electron-withdrawing groups in the π system.

5. How do O- and COO- compare to other electron releasing groups in a π system?

O- and COO- are considered strong electron releasing groups in a π system due to their negative charge and ability to delocalize electrons through resonance. Other common electron releasing groups include -OH, -OR, and -NH2, which also have lone pairs of electrons that can donate into the π system through resonance.

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