Cyclohexanol Synthesis Lab Report

Experimental

Clay-catalyzed dehydration of cyclohexanol

Cyclohexanol (10.0336 g, mmol) was added to a 50 mL round bottom flask containing five boiling chips, Montmorillonite K10 clay (1.0430 g) was then added to the cyclohexanol and the mixture was swirled together. The flask was then placed in a sand bath and attached to a simple distillation apparatus. The contents of the flask were then heated at approximately 150 °C to begin refluxing the cyclohexanol. The distillation flask was then loosely covered with aluminum foil and the hood sash was lowered in order to minimize airflow. As the reaction continued, the temperature was adjusted in order to maintain a consistent rate of distillation. When the distillation was complete, the heat was removed, allowing the clay to cool. The cyclohexene product contained within the collection flask was transferred to a scintillation vial and massed, revealing that 0.9273 g (11.31 mmol) of product was collected. Using the acquired mass of the product a percent yield value of 11.31% was found. The percent yield value was calculated by dividing the product yield obtained from the experiment (in mmol) ( m_A) by the theoretical yield (m_T) and multiplying that value by 100%.

Percent yield of cyclohexene:

% recovery= ((m_A ))/((m_T))•100%

% recovery= ((11.31 mmol))/((100.1 mmol))•100%

%

An addition funnel containing 30% H2O2 was attached to round bottom flask. The flask was then placed in an ice-water bath and allowed to stir and cool. After cooling for five minutes, the H2O2 was added dropwise to the reaction flask. As Br2 formed, the solution began to produce a reddish brown color. Once all of the H2O2 was added, the cyclohexene (1.03 g, 12.6 mmol) produced from the first experiment was then poured into the addition funnel. In a fashion similar to the H2O2, the cyclohexene was added to the reaction flask in a dropwise