Products: 1-methylcyclohexene, 3-methylcyclohexene, methylenecyclohexane A) Which kind of mechanism can better account for the product mixture obtained from the dehydration of cis and trans 2-methylcyclohexanol: E1, E2, or a combination of the two?
B) Write detailed mechanisms explaining the formation of all the observed products.

See explanation

Explanation:

The reaction that we are considering here is quite a knotty reaction. It is difficult to decide if the mechanism is actually E1 or E2 since both are equally probable based on the mass of scientific evidence regarding this reaction. However, we can easily assume that the methylenecyclohexane was formed by an E1 mechanism.

Looking at the products, one could convincingly assert that the reaction leading to the formation of the two main products proceeds via an E1 mechanism with the formation of a carbocation intermediate as has been shown in mechanism attached to this answer. Possible rearrangement of the carbocation yields the 3-methylcyclohexene product.

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