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Topic: question in carbocation rearrangement  (Read 2274 times)

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Offline HB

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question in carbocation rearrangement
« on: September 25, 2013, 02:10:27 PM »
is it true that primary carbocation rearrange to tertary carbocation and not secondary carbocation.
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Offline magician4

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Re: question in carbocation rearrangement
« Reply #1 on: September 25, 2013, 06:24:15 PM »
I'm not aware of any rule stating so

In contrary, I'm aware of examples proving the opposite
http://pubs.rsc.org/en/content/articlepdf/1963/JR/JR9630001938

so: rearrangements to tert. structures often do occur, yes, but rearrangements to sec. structures are by no means forbidden (and are proven to occur, too)


regards

Ingo
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Offline spirochete

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Re: question in carbocation rearrangement
« Reply #2 on: September 25, 2013, 10:45:19 PM »
General rule: Carbocations rearrange to make more stable carbocations.

Exception: if rearrangement to a less stable carbocation is followed by rearrangement to an even more stable one than you started with, occasionally that will happen.  Not usually in undergrad classes, though.
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Offline antimatter101

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Re: question in carbocation rearrangement
« Reply #3 on: September 26, 2013, 03:49:05 AM »
To truly understand this topic, go on Google and search up:
-Hyperconjugation
-Alkyl shift
-Halide shift
Electrostatic potential maps if possible. My chemistry book has tons of them!
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