Why can't the phenyl cation be stabilized by resonance?

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In summary, the conversation discusses the inability of the phenyl cation to be stabilized by resonance. The conditions for resonance are met, but the rearrangement of the cation through a hydride shift is unfavorable. The idea that the carbon atom with a positive charge must be sp-hybridized is also questioned. Drawing out resonance structures may provide further explanation.
  • #1
Ashu2912
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In my book, it's written that the phenyl cation can't be stabilized by resonance. I can't think of any reason why this is so. All the conditions for resonance are satisfied : all carbon atoms lie in one plane, all possible canonical structures will have the same number of unpaired electrons, we'll only move the pi - electrons.
Also, I think that the carbon atom having positive charge must be sp - hybridized, as per the orbital diagram, but I guess even that is incorrect. Can anyone explain this?
 
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  • #2
Try drawing out the resonance structures.
 
  • #3
The only way to rearrange a phenyl cation would be a hydride shift, which is unfavorable.
 

Related to Why can't the phenyl cation be stabilized by resonance?

1. What is a phenyl cation?

A phenyl cation is a positively charged molecule that contains a benzene ring. It is formed when a benzene ring loses a hydrogen atom and gains a positive charge, making it an unstable species.

2. Why is the stability of phenyl cation important?

The stability of phenyl cation is important because it can influence the reactivity of organic compounds. Understanding the stability of phenyl cation can help predict the products of chemical reactions and design more efficient synthetic routes.

3. How is the stability of phenyl cation determined?

The stability of phenyl cation is determined by several factors, including resonance, inductive effects, and hyperconjugation. These factors affect the distribution of electrons in the molecule, which can either stabilize or destabilize the cation.

4. What are some methods used to stabilize phenyl cation?

One method to stabilize phenyl cation is to introduce electron-donating groups, such as alkyl or aryl groups, onto the benzene ring. These groups can donate electrons to the cation, making it more stable. Another method is to use a solvent that can solvate the cation, reducing its charge and increasing its stability.

5. Can the stability of phenyl cation be predicted?

Yes, the stability of phenyl cation can be predicted using computational methods, such as molecular orbital theory. These methods can calculate the energy of the cation and predict its reactivity. However, experimental data is still needed to confirm the predicted stability.

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