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
Outline a mechanism for the dehydration of 2-methylcyclohexanol into 1-methylcyclohexene catalyzed by acid. (include all arrows, charges, and intermediates)
Frequently Asked Questions
What scientific concept do you need to know in order to solve this problem?
Our tutors have indicated that to solve this problem you will need to apply the Dehydration Reaction concept. You can view video lessons to learn Dehydration Reaction. Or if you need more Dehydration Reaction practice, you can also practice Dehydration Reaction practice problems.