November 30, 2023, 02:56:13 AM
Forum Rules: Read This Before Posting

Topic: [urgent] hydration mechanism ring strain  (Read 1433 times)

0 Members and 1 Guest are viewing this topic.

Offline ostudent

  • Regular Member
  • ***
  • Posts: 31
  • Mole Snacks: +1/-0
[urgent] hydration mechanism ring strain
« on: September 16, 2018, 09:08:40 PM »
Hi all,

I'm sorry about the 'urgent' plug. My exam is tomorrow.
I would like to understand precisely why the ethenylcyclobutane doesn't yield a tertiary carbocation at the third step by hydride shift and instead shifts to a cyclopentane with a secondary carbocation before rearranging to a tertiary carbocation.

If it is due to ring strain, does this type of mechanism apply to all rings of this format?

Thank you a thousand times.

Offline sjb

  • Global Moderator
  • Sr. Member
  • ***
  • Posts: 3651
  • Mole Snacks: +222/-42
  • Gender: Male
Re: [urgent] hydration mechanism ring strain
« Reply #1 on: September 17, 2018, 04:53:17 AM »
What other factors affect stability?

Sponsored Links