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Mechanism of acid-catalyzed ring opening of a cyclopropane ring
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Mickey Curran
Mechanism of acid-catalyzed ring opening of a cyclopropane ring
I believe the mechanism should be somewhat like this (after the formation of carbocation) -
It would account for the product shown, but I am not sure if it's correct. I feel it's more favourable for a dehydration to occur with the hydrogen from the ring itself (shown on the dash at the top) to form this -
This double bond is conjugated and more substituted, so I should have thought that this would be the major product.
I believe the mechanism should be somewhat like this (after the formation of carbocation) -
It would account for the product shown, but I am not sure if it's correct. I feel it's more favourable for a dehydration to occur with the hydrogen from the ring itself (shown on the dash at the top) to form this -
This double bond is conjugated and more substituted, so I should have thought that this would be the major product.
@Mithoron Thanks for the insight. Yes, if its a single step then to form my proposed product it would need to start making a double bond before the ring was completely broken - which of course would be difficult owing to angle strain.More
I believe the mechanism should be somewhat like this (after the formation of carbocation) -
It would account for the product shown, but I am not sure if it's correct. I feel it's more favourable for a dehydration to occur with the hydrogen from the ring itself (shown on the dash at the top) to form this -
This double bond is conjugated and more substituted, so I should have thought that this would be the major product.
I believe the mechanism should be somewhat like this (after the formation of carbocation) -
It would account for the product shown, but I am not sure if it's correct. I feel it's more favourable for a dehydration to occur with the hydrogen from the ring itself (shown on the dash at the top) to form this -
This double bond is conjugated and more substituted, so I should have thought that this would be the major product.
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