Which is more stable: carbocation or carbanion?

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In summary, carbocation is more stable than carbanion due to the presence of donor groups that stabilize the positive charge. Carbanions, on the other hand, are less stabilized and more reactive due to their sp3 hybridization and lone pair of electrons. This makes them act as free radicals.
  • #1
ashishsinghal
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Is carbocation more stable than carbanion. Why or why not? I feel carbanion should be more stable because the octet of carbon is complete. Is it correct?
 
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  • #2
That is an interesting question but it is difficult to answer precisely because I can't think of any conditions that would allow for both to exist. I would also vote for carbanions because that stay intact in solution after you generate them. Carbocations tend to rearrange and give mixtures very quickly.
 
  • #3
Yes carbocation is more stable. let's take for example the ter-butyl carbocation (Ch3)3-C+ this charged ion is highly stabilized due to the presence of the three donor methly groups that donate electrons, and hence largely stabilize the positive charge.
On the other hand the tert-butyl carbanion (CH3)3-C- would be less stabilized and more reactive than its positive catine since The negatively charged carbon atom in carbanion is sp3 hybridized. Therefore, it has a tetrahedral structure. Three of the four sp3 hybridized orbitals form 3s-bonds with hydrogen or carbon atom of the alkyl group. The fourth sp3 hybrid orbital contains the lone pair of electrons.This would cause to bring the reactivity to this ion and makes it act as a free radicals (check for the reactivity of free radicals).
 

1. What is a carbocation?

A carbocation is a positively charged carbon atom that is missing an electron. It is a reactive intermediate in organic chemistry reactions.

2. What is a carbanion?

A carbanion is a negatively charged carbon atom that has gained an extra electron. It is also a reactive intermediate in organic chemistry reactions.

3. How do carbocations and carbanions differ?

The main difference between carbocations and carbanions is the presence or absence of an extra electron. Carbocations have a positive charge, while carbanions have a negative charge. This difference affects their stability and reactivity in chemical reactions.

4. What are the properties of carbocations and carbanions?

Carbocations are highly reactive and unstable due to their positive charge, and they tend to undergo reactions to regain stability. Carbanions, on the other hand, are more stable due to their negative charge and are less reactive. They often act as nucleophiles in chemical reactions.

5. How are carbocations and carbanions used in organic synthesis?

Carbocations and carbanions are key intermediates in many organic synthesis reactions, allowing for the creation of complex molecules. They can be used to form new carbon-carbon bonds and introduce functional groups into organic compounds.

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