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Organic Chemistry 1

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Epoxide Opening Carbocations

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When the following epoxide is treated with acid, the protonated epoxide can open to form two possible carbocations. The three cation intermediates can be considered to be like resonance structures of each other.

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

Which carbocation is more stable?

A

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

B

Ross V. Weatherman. Created for Albert.io. Copyright 2016. All rights reserved.

C

They are both of equivalent energy.