We’re being asked to draw the product of the given reaction.
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.
Also, 1˚ alcohols that can rearrange into 3˚ follow this mechanism.
Draw the Zaitsev product formed when 2,3-dimethylpentan-3-ol undergoes an E1 dehydration.
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