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Topic: carbocation rearrangement  (Read 3120 times)

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Offline phymatter

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carbocation rearrangement
« on: March 24, 2011, 10:52:12 AM »
if there is a choice between H , CH3 and Phenyl group for rearrangement to stabalize a carbocation , what is the preference followed ? is there no exception to this rule ??
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Offline Grundalizer

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Re: carbocation rearrangement
« Reply #1 on: March 24, 2011, 01:46:51 PM »
Which of those functional groups would be better for stabilizing a charge?

 The positive "+" charge is going to sit on a carbon, so which one of those has more carbons? 

Hydrogen is out of the question, so which do you think is better between a methyl group and phenyl group?  Which one has more resonance structures?  Multiple resonance structures is a good indication of an organic compound being able to stabilize charge

Offline Honclbrif

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Offline phymatter

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Re: carbocation rearrangement
« Reply #3 on: March 24, 2011, 11:29:36 PM »
if phenyl shift takes place the crbocation will not be stabilized by resonance :

consider 2 cases :
carbocation is stabilized by :
1.2 methyl groups
2.1 methyl and 1 phenyl group , which will be more stable ???

please *delete me*!

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