0 votes
24 views
ago in Organic Chemistry by (34.3k points)
Identify the reaction intermediate and propose a detailed mechanism for the acid-catalyzed hydration of 1-methylcyclohexene to form a tertiary alcohol.

1 Answer

0 votes
ago by (34.3k points)
In the acid-catalyzed hydration of 1-methylcyclohexene, the reaction intermediate is a carbocation, specifically a tertiary carbocation. The mechanism for this reaction can be described in the following steps:1. Protonation of the alkene: The reaction begins with the protonation of the double bond in 1-methylcyclohexene by a strong acid, such as sulfuric acid  H2SO4  or hydrochloric acid  HCl . This results in the formation of a more stable tertiary carbocation intermediate, as the positive charge is located on the more substituted carbon.1-methylcyclohexene + H  [1-methylcyclohexyl]+2. Nucleophilic attack by water: The carbocation intermediate formed in the first step is then attacked by a water molecule, which acts as a nucleophile. The oxygen atom in the water molecule donates a pair of electrons to form a bond with the positively charged carbon, resulting in the formation of an oxonium ion.[1-methylcyclohexyl]+ + H2O  [1-methylcyclohexyl-OH2]+3. Deprotonation: In the final step, the oxonium ion loses a proton to another water molecule or a conjugate base from the acid used in the first step  such as HSO4 or Cl . This results in the formation of the tertiary alcohol product, 1-methylcyclohexanol, and regenerates the acid catalyst.[1-methylcyclohexyl-OH2]+ + H2O  1-methylcyclohexanol + H3OOverall, the acid-catalyzed hydration of 1-methylcyclohexene proceeds through a tertiary carbocation intermediate, with the final product being 1-methylcyclohexanol.
Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...