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Topic: Loss of LG result in resonance-stabilized carbocation  (Read 1453 times)

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Offline ostudent

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Loss of LG result in resonance-stabilized carbocation
« on: June 12, 2018, 07:30:45 PM »
Hi all,

I am curious to know why the loss of chloride does not result in a resonance-stabilized carbocation for the following compound?

I believe the resonance structures would look like figure 2.
Is it simply wrong because double bonds cannot be oriented non-linearly?

Thank you for the feedback.
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Offline Enthalpy

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Re: Loss of LG result in resonance-stabilized carbocation
« Reply #1 on: June 13, 2018, 04:20:58 AM »
The aromatic ring is already a very efficient resonance.
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Offline mjc123

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Re: Loss of LG result in resonance-stabilized carbocation
« Reply #2 on: June 13, 2018, 04:28:33 AM »
You can't have double bonds next to each other in a benzene ring.

The empty orbital in the phenyl cation is an in-plane sp2 orbital that does not participate in resonance with the pi orbitals.
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