March 28, 2024, 11:09:31 AM
Forum Rules: Read This Before Posting


Topic: Carbocation rearrangement question  (Read 673 times)

0 Members and 1 Guest are viewing this topic.

Offline sharbeldam

  • Full Member
  • ****
  • Posts: 344
  • Mole Snacks: +8/-2
Carbocation rearrangement question
« on: July 30, 2020, 07:50:59 AM »
The question lies in the picture below, my first question is, can groups other than alkyl/hyride shift as well like this in the picture? it's not too large?
And if they can, why wouldn't the benzene ring shift instead since it's the smallest.
the teacher said the first product would happen but why? the carbocation wouldn't be as stable because NO2 is electron withdrawing and it would make the carbocation less stable...

Any explanation?
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21

Offline rolnor

  • Chemist
  • Sr. Member
  • *
  • Posts: 2203
  • Mole Snacks: +148/-10
Re: Carbocation rearrangement question
« Reply #1 on: July 30, 2020, 09:44:40 AM »
You need to draw the mecanism to understand why p-methoxy but not p-nitro can rearrange this way.

Offline sharbeldam

  • Full Member
  • ****
  • Posts: 344
  • Mole Snacks: +8/-2
Re: Carbocation rearrangement question
« Reply #2 on: July 30, 2020, 09:50:49 AM »
So this is not normal shift? like not same mechanism as hydride/methyl shift?
If not, any link for the mechanism?
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21

Offline sharbeldam

  • Full Member
  • ****
  • Posts: 344
  • Mole Snacks: +8/-2
Re: Carbocation rearrangement question
« Reply #3 on: July 31, 2020, 05:19:04 AM »
anyone has a link for the suggested mechanism that shows that only activating groups can rearrange?
O-Chem 1+2 Online Free tutor on Skype: Live:damnitsjake21

Sponsored Links