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how to determine the stability of a cabocation and carboanion

how to determine the stability of a cabocation and carboanion
 
 

Grade:11

4 Answers

crazycoolguy
20 Points
6 years ago

The stability and reactivity of a carbanion is determined by several factors. These include

1)The inductive effect. Electronegative atoms adjacent to the charge will stabilize the charge;

2)Hybridization of the charge-bearing atom. The greater the s-character of the charge-bearing atom, the more stable the anion;

3)The extent of conjugation of the anion. Resonance effects can stabilize the anion. This is especially true when the anion is stabilized as a result of aromaticity.

crazycoolguy
20 Points
6 years ago
We know that methyl group is electron releasing i.e. has +I inductive effect. The alkyl group attached to positively charged carbon atom tends to release electrons towards carbon. This decreases the positive charge on the carbon atom but the carbon itself is somewhat positive. As a result, the positive charge on the carbon atom gets dispersed, giving it stability. Therefore, more the number of alkyl groups, the greater will be the dispersal of charge and therefore, more stable will be the carbocation.
 

Thus, tertiary carbocation in which there are three alkyl groups attached to positive carbon is more stable than a secondary carbocation with two alkyl groups. Similarly, a secondary carbocation is more stable than a primary carbocation, which in turn is more stable than methyl carbocation:

 
Thus, the order of stability is: CH3+ o o o
 

Other carbocations are benzyl carbocation, which is primary in nature but is highly stable because of resonance stabilization.

 

Triphenyl carbocation, Ph3C+ is the most stable because of resonance stabilization among three phenyl groups.

Sweta Mishra
37 Points
6 years ago
Carbocations are electron deficient species, so if any electron donating group attached will increase the stability of carbocations. Hence tertiary carbocations are more stable. It depends upon inductive effect and hyperconjugation effect.On the other hand, carbanions are electron rich species so stability order is reversed as compared to carbocations.It depends upon inductive effect and resonance effect.
Upendra Yadav
33 Points
6 years ago
The stability and reactivity of a carbanion is determined by several factors . 
any electron donating group attached will increase the stability of carbocations. Hence tertiary carbocations are more stable. It depends upon inductive effect and hyperconjugation effect.On the other hand, carbanions are electron rich species so stability order is reversed as compared to carbocations.It depends upon inductive effect and resonance effect.any electron donating group attached will increase the stability of carbocations. Hence tertiary carbocations are more stable. It depends upon inductive effect and hyperconjugation effect.On the other hand, carbanions are electron rich species so stability order is reversed as compared to carbocations.It depends upon inductive effect and resonance effect.

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