The dehydration of Cyclohexanol requires going through an acid-catalyzed elimination of water for the synthesis of cyclohexane from cyclohexanol. To get cyclohexane from cyclohexanol you must remove the cycloalkane with fractional distillation, drying with anhydrous sodium sulfate, and analyzed by GC data and the bromine test.
The reaction we are trying to accomplish going from cyclohexanol to cyclohexene is a secondary alcohol going through an E1 reaction. This is the unimolecular elimination reaction in which Zaitsev’s rule applies where the most substituted alkene is formed. In a unimolecular elimination, the leaving group leaves to form a carbocation where the base removes a proton which results in an alkene
The set up for the fractional distillation is slightly complicated. The round bottom flask with the cyclohexanol mixture sits inside of the depression of a heating mantle. All glass pieces clamp together with blue clips. The flask attaches to a vertical …show more content…
Set up fractional distillation and attach the round bottom flask with the mixture, and heat over a heating mantle. An ice bath was placed under the receiving flask of the fractional distillation set up. The distillation product was collected from 60°C to 28°C. At the last drop the heating mantle was unplugged and removed and the receiving flask was weighed. 2 teaspoons of anhydrous sodium sulfate were added and swirled until the water was removed and the product was ‘dried’. The product was decanted from the anhydrous sodium sulfate crystals into another round bottom flask. This round bottom flask was pre-weighed and then weighed after the addition of the product for the weight of crude cyclohexene. A few drops of the pure product went into a GC tube for analysis. A few drops were added to a test tube and 2 drops of bromine were added for the bromine
The reaction we are trying to accomplish going from cyclohexanol to cyclohexene is a secondary alcohol going through an E1 reaction. This is the unimolecular elimination reaction in which Zaitsev’s rule applies where the most substituted alkene is formed. In a unimolecular elimination, the leaving group leaves to form a carbocation where the base removes a proton which results in an alkene
The set up for the fractional distillation is slightly complicated. The round bottom flask with the cyclohexanol mixture sits inside of the depression of a heating mantle. All glass pieces clamp together with blue clips. The flask attaches to a vertical …show more content…
Set up fractional distillation and attach the round bottom flask with the mixture, and heat over a heating mantle. An ice bath was placed under the receiving flask of the fractional distillation set up. The distillation product was collected from 60°C to 28°C. At the last drop the heating mantle was unplugged and removed and the receiving flask was weighed. 2 teaspoons of anhydrous sodium sulfate were added and swirled until the water was removed and the product was ‘dried’. The product was decanted from the anhydrous sodium sulfate crystals into another round bottom flask. This round bottom flask was pre-weighed and then weighed after the addition of the product for the weight of crude cyclohexene. A few drops of the pure product went into a GC tube for analysis. A few drops were added to a test tube and 2 drops of bromine were added for the bromine