The alcohol shown is heated with concentrated sulfuric acid. Which structure is the major product?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

The alcohol is 1-methylcyclohexanol, a tertiary alcohol that dehydrates by the E1 route through a tertiary carbocation. Loss of a ring hydrogen gives the more substituted, more stable endocyclic alkene 1-methylcyclohexene (Saytzeff). Methylenecyclohexane is minor.

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