Do alkenes only form carbocations while carbonyl groups only form carbanions?

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In summary, the conversation discusses the reactivity of carbocations and carbanions, and the difference between homolytic and heterolytic cleavage. It also clarifies that carbonyl carbons do not form carbanions and that homolytic cleavage does not result in positive or negative charge.
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brake4country
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Homework Statement


Do alkenes only form carbocations while carbonyl groups only form carbanions?

Homework Equations


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The Attempt at a Solution


I understand the relative reactivity of carbocations and carbanions. How does one know when an organic compound follows heterolytic cleavage or homolytic cleavage of H? For example, do alkenes only make carbocations while ketones and aldehydes create carbanions?
 
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  • #2
You are mixing up quite a few things here and it is very difficult to give you an answer. Let's clear up some terminology and ideas here.

Carbonyl carbons do not form carbanions. In fact, carbonyl carbons have quite a bit of carbocation character, thus they are attacked by nucleophiles (think formation of an amide or any other -COOH type of chemistry).

Homolytic versus heterolytic cleavage does not result in postive versus negative charge. Homolytic cleavage leaves neutral molecules whereas homolytic cleavage will result in one positively and one negatively charged molecule. Please draw these out for yourself.

Please think about some of these ideas/terms and come back with any further questions.
 

1. What are carbocations and carbanions?

Carbocations and carbanions are chemical species that contain a carbon atom with an incomplete octet. Carbocations have a positive charge on the carbon atom, while carbanions have a negative charge.

2. How do carbocations and carbanions differ in stability?

Carbocations are less stable than carbanions due to the positive charge on the carbon atom, which makes them highly reactive. Carbanions, on the other hand, are more stable due to the negative charge, making them less reactive.

3. What factors influence the stability of carbocations and carbanions?

The stability of carbocations and carbanions depends on the inductive effect, resonance, and hyperconjugation. The inductive effect refers to the ability of neighboring atoms to influence the distribution of electrons in the molecule. Resonance occurs when electrons can delocalize and stabilize the charge. Hyperconjugation also contributes to stability by allowing the delocalization of electrons through the overlap of sigma bonds.

4. How do carbocations and carbanions participate in reactions?

Carbocations are electrophilic, meaning they are electron-deficient and can accept electrons from a nucleophile to form a new bond. Carbanions, on the other hand, are nucleophilic, meaning they are electron-rich and can donate electrons to form a new bond with an electrophile.

5. What are some common reactions involving carbocations and carbanions?

Some common reactions involving carbocations include electrophilic addition, electrophilic substitution, and rearrangement reactions. Carbanions are often involved in nucleophilic substitution, nucleophilic addition, and elimination reactions.

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