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Topic: [urgent] hydration mechanism ring strain  (Read 1480 times)

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Offline ostudent

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[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

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Re: [urgent] hydration mechanism ring strain
« Reply #1 on: September 17, 2018, 04:53:17 AM »
What other factors affect stability?

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