Dehydrating Cyclohexanol

Topics: Distillation, Oxygen, Water Pages: 3 (722 words) Published: March 13, 2013
Dehydrating Cyclohexanol

The purpose of the lab experiment is to prepare cyclohexene from cyclohexanol through an acid-catalyzed dehydration. In order to produce the cyclohexene from cyclohexanol, an elimination reaction was performed. First by protonating the oxygen of the alcohol and creating an oxonium ion we replaced the poor leaving group (OH) into a better leaving group (OH2+). Second, dehydrating the cyclohexanol using phosphoric acid and sulfuric acid as acid catalysts and heat to create a charged carbocation which then creates the carbon-carbon pi bond of cyclohexene from the release of a proton that is adjacent to the positively charged carbon. As a result we were able to distill a total of 2.5098 grams of cyclohexene

Reaction Scheme and/or structure of compounds used

Compounds used:


Molecular formula: C6H12O
Molar Mass: 100.158 g/mol
Density: .962 g/ml, liquid
Melting point: 25.93 C
Boiling point: 160.84 C

Phosphoric Acid
Molecular Formula: H3PO4
Molar Mass: 97.995 g/mol
Density: 1.885 g/mL , liquid
Melting point: 42.35 C (anhydrous)
Boiling point: 158 C (decomp)

Sulfuric Acid
Molecular Formula: H2SO4
Molar Mass: 98.079 g/mol
Density: 1.84 g/cm3
Melting point: 10 C
Boiling point: 337 C

Results and Discussion:

To begin the procedure of dehydrating cyclohexanol into cyclohexene, we assembled a simple distillation apparatus, using a heating element that did not include a flame. The reason behind this is because the cyclohexene is highly flammable, so as to remove any unnecessary risk we used a heating pad. We then created our cyclohexanol mixture of cylcohexanol (6mL), sulfuric acid (10 drops), phosphoric acid (8 mL), and a boiling cheap which we then used on our apparatus. We heated the mixture to no more than 88 C so as to be sure we distilled all the cyclohexene, and not the phosphoric, sulfuric, and cyclohexanol. Having distilled our mixture to a temperature of 88...
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