Theory of synthesis of cyclohexane from cyclohexanol by acid catalyzed (E1) elimination?
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Apr 13
The synthesis of cyclohexane from cyclohexanol by acid-catalyzed (E1) elimination involves the following steps:
1. Protonation of the hydroxyl group: The first step in the reaction is the protonation of the hydroxyl group in cyclohexanol by an acid catalyst, such as sulfuric acid (H2SO4). This protonation makes the hydroxyl group a better leaving group.
2. Formation of a carbocation: The protonated hydroxyl group undergoes dehydration, resulting in the formation of a carbocation intermediate. The carbocation is stabilized by the delocalization of the positive charge over the cyclohexane ring.
3. Rearrangement (if necessary): In some cases, the carbocation may undergo a rearrangement to form a more stable carbocation intermediate.
4. Deprotonation: The final step in the reaction is the deprotonation of the carbocation intermediate by a base, such as water or another alcohol molecule. This deprotonation results in the formation of cyclohexane.
Overall, the acid-catalyzed (E1) elimination of cyclohexanol to form cyclohexane involves the dehydration of the hydroxyl group to form a carbocation intermediate, followed by deprotonation to yield the desired product.