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What is the mechanism of acid-catalyzed dehydration of 1-methoxy-2-methylcyclohexane to yield methylenecyclohexane, and how would the mechanism change if a proton scavenger was added to the reaction mixture?

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ago by (190 points)
The acid-catalyzed dehydration of 1-methoxy-2-methylcyclohexane to yield methylenecyclohexane involves the following steps:1. Protonation of the oxygen atom in the methoxy group by a strong acid  e.g., H2SO4 or H3PO4 . This step generates a positively charged oxonium ion.2. The oxonium ion undergoes a 1,2-alkyl shift  a rearrangement involving the migration of the methyl group from the 2-position to the 1-position . This migration results in the formation of a carbocation at the 2-position of the cyclohexane ring.3. Loss of a proton from the carbocation to form a double bond, resulting in the formation of methylenecyclohexane.4. Deprotonation of the conjugate acid of the catalyst by the solvent or another molecule of the starting material, regenerating the acid catalyst.If a proton scavenger  a base  is added to the reaction mixture, it will compete with the methoxy group for the proton from the acid catalyst. This competition can slow down or even inhibit the formation of the oxonium ion, which is the first step in the dehydration mechanism. As a result, the overall rate of the reaction may decrease, and the yield of methylenecyclohexane may be reduced. Additionally, the proton scavenger may react with the carbocation intermediate, leading to the formation of side products.

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