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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: ostudent on September 16, 2018, 09:08:40 PM

Title: [urgent] hydration mechanism ring strain
Post by: ostudent 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.
Title: Re: [urgent] hydration mechanism ring strain
Post by: sjb on September 17, 2018, 04:53:17 AM
What other factors affect stability?