Problem: Outline a mechanism for the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene catalyzed by acid. (include all arrows, charges, and intermediates)

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Given reaction: Alcohol + Strong Acid → Dehydration → Alkene

Dehydration of  Alcohol → protonation + E2 elimination


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


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Problem Details

Outline a mechanism for the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene catalyzed by acid. (include all arrows, charges, and intermediates)

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