Question

Draw a structural formula of an alkene or alkenes (if more than one) that undergo acid-catalyzed hydration and without rearrangement give 1-methylcyclohexanol as the MAJOR product. Ignore stereochemistry. If your answer includes more than one alkene, just draw both structures. Do not separate the formulas with + or any other sign.

Answer 1

See explanation and image attached

Step-by-step explanation:

The acid-catalyzed hydration of alkenes is an ionic reaction. Being an ionic reaction, a carbocation is formed in the process. This carbocation is capable of rearrangement to yield different products based on thermodynamic stability.

Remember that the order of stability of carbocations is; methyl< primary<secondary< tertiary. The rearrangement of carbocations leads to the formation of more stable intermediates and consequently more stable products.

However, the alkene in the image shown yields 1-methylcyclohexanol without carbocation rearrangement.