Question

In lab we reacted 4-Methylcyclohexanol with sulfuric acid to give 4-Methylcyclohexene. We would expect 4-Methylcyclohexanol to only yield one product; however, the reaction produces isomers. This is not a case of a hydride shift or methyl shift, it is actually a result of the equilibrium that exists during the reaction.

Give the structures of ALL the possible methyl cyclohexene isomers and write the mechanism for the formation of the other isomers.