Problem: Draw the major organic product formed when the compound shown below is heated with H2SO4.

FREE Expert Solution

For this problem, 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.


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Problem Details

Draw the major organic product formed when the compound shown below is heated with H2SO4.