Final answer:
The conversion of cyclohexanol to cyclohexene is a dehydration reaction under acidic conditions, typically involving sulfuric or phosphoric acid. It proceeds through the protonation of the hydroxyl group, formation of a carbocation intermediate, and finally the elimination of a hydrogen atom to form the double bond of cyclohexene.
Step-by-step explanation:
Mechanism of Conversion of Cyclohexanol to Cyclohexene
The conversion of cyclohexanol to cyclohexene involves a dehydration reaction, which is a common type of elimination reaction in organic chemistry. Specifically, this transformation involves the removal of a water molecule (H2O) from cyclohexanol under acidic conditions to form cyclohexene. The typical acid used for this reaction is sulfuric acid or phosphoric acid, which helps to protonate the hydroxyl group (-OH) of cyclohexanol, making it a better leaving group. In the first step, the alcohol is protonated to form water, which is a good leaving group. Next, the departure of the water molecule leads to the formation of a carbocation intermediate. Lastly, a hydrogen atom is removed from the adjacent carbon, resulting in the formation of a double bond and producing cyclohexene as the final product.
The reaction is generally carried out by heating the mixture of cyclohexanol and the acid to promote the dehydration process. The reaction conditions need to be controlled carefully to prevent further reactions such as polymerization or cracking of the formed cyclohexene.
It is important to note that while the Diels-Alder reaction is an important synthetic mechanism in organic chemistry, it is not the mechanism by which cyclohexanol is converted to cyclohexene. Instead, the Diels-Alder reaction involves the formation of a six-member ring through the cycloaddition of a diene and a dienophile.