Frequently Asked Question

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The order of stability of carbonion is

Accepted Answer

The order of stability of carbanions is generally determined by the following factors:
1. Electron-donating groups: Groups that donate electrons to the carbanion stabilize it by delocalizing the negative charge. For example, alkyl groups are electron-donating and stabilize carbanions.
2. Electron-withdrawing groups: Groups that withdraw electrons from the carbanion destabilize it by increasing the negative charge density. For example, halogens are electron-withdrawing and destabilize carbanions.
3. Resonance: If the carbanion can delocalize its negative charge through resonance, it is stabilized.
4. Hybridization: Carbanions with sp3 hybridization are less stable than those with sp2 or sp hybridization because the negative charge is more concentrated on the carbon atom in sp3 hybridization.
Therefore, the order of stability for carbanions is:

Primary carbanion
Benzylic carbanion > Allylic carbanion > Alkyl carbanion
Carbanions with resonance stabilization > Carbanions without resonance stabilization
Carbanions with sp hybridization > Carbanions with sp2 hybridization > Carbanions with sp3 hybridization


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