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Cyclohexanol Lab Report

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In the experiment, the cyclohexanol solution is used to perform the dehydration process. Cyclohexanol is a six carbon aromatic hydrocarbon with 1 of the hydrogen atoms is substituted by 1 hydroxyl group, OH-. Through dehydration reaction, the hydroxyl group of cyclohexanol is removed causing formation of cyclohexene. Cyclohexene is a six carbon hydrocarbon with a single double bond. Cyclohexanol will undergo E1 elimination mechanism to form cyclohexene. This elimination reaction will cause the loss of a small H-X molecule from adjacent carbon resulting in formation of pi bond. All the E1 mechanism reaction will undergo a process known as heterolytic bond cleavage. The condition for this heterolytic cleavage to occur is when one atom leaves a compound with both of the original bond’s electrons. This will lead to formation of ions. For example, elimination of H-X from an organic compound involves the loss of a proton and a …show more content…

For dehydration of cyclohexanol, phosphoric acid is used. The phosphoric acid protonates the most basic atom(oxygen atom) in the cyclohexanol and promotes the conversion of the very poor leaving group (HO-) into a good leaving group (water,H2O). The protonation of oxygen atom atom lower the pka value of leaving group(water) from 16 down to ≈ 0(H3O+). The lowered pka value will then promote the departure of the leaving group(water) and leave behind a 2° carbocation intermediate. Then, the base (water is the base that present in the highest concentration) removes a proton from a β-carbon( a carbon adjacent to the positively charged carbon) and forms an alkene(cyclohexene). The phosphoric acid will then regenerated. For dehydration of cyclohexanol, only cyclohexene is produced. But for others alcohol, acid catalyzed dehydration may lead to more than 1 elimination product. The major product will be the more stable alkene as it has the more stable transition state leading to its

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