Dismiss Notice
Join Physics Forums Today!
The friendliest, high quality science and math community on the planet! Everyone who loves science is here!

Stability of phenyl cation

  1. May 23, 2012 #1
    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???
     
  2. jcsd
  3. May 23, 2012 #2
    Try drawing out the resonance structures.
     
  4. May 24, 2012 #3
    The only way to rearrange a phenyl cation would be a hydride shift, which is unfavorable.
     
Know someone interested in this topic? Share this thread via Reddit, Google+, Twitter, or Facebook




Similar Discussions: Stability of phenyl cation
  1. Cation Solubility (Replies: 3)

  2. Phenyl and methyl shift (Replies: 10)

Loading...