Consider the dehydration of 1-methylcyclohexanol in the presence of concentrated H ₂ SO ₄ . What is the correct order of the relative yields of the following products? (I) (II) (III)

Step-by-step solution

The dehydration of 1-methylcyclohexanol in the presence of concentrated H ₂ SO ₄ proceeds via an E1 mechanism. Protonation of the hydroxyl group followed by the loss of a water molecule generates a stable tertiary carbocation, the 1-methylcyclohexyl cation. This carbocation can lose a proton from adjacent carbon atoms to form different alkenes. Loss of a proton from the adjacent ring carbons yields 1-methylcyclohexene (III). This is a trisubstituted, endocyclic alkene, which is the most stable product. According to