Problem: What alkene(s) would be produced from the dehydration of cyclopentanol?

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We are asked what alkene(s) would be produced from the dehydration of cyclopentanol




Recall that alcohols are converted to alkenes via acid-catalyzed dehydration. The mechanism depends on the type of alcohol involved:

For 1˚ alcohols:

(1) protonation – the –OH group is protonated by the acid catalyst to give H2O, a better leaving group

(2) E2 β-elimination – the conjugate base removes a β-hydrogen via E2, reforming the acid catalyst in the process


For 2˚ and 3˚ alcohols:

(1) protonation – the –OH group is protonated to give a better leaving group, H2O

(2) carbocation formation – the carbon-H2O bond is broken

(3) E1 β-elimination – the conjugate base removes a β-hydrogen via E1, reforming the acid catalyst in the process


Since a carbocation is formed in this mechanism, the carbocation may rearrange into a more stable one.


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What alkene(s) would be produced from the dehydration of cyclopentanol?

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