Cyclohexanol to Cyclohexene

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Experiment 5: Preparation of Cyclohexene- Acid Catalyzed Elimination of Cyclohexanol Ball State University Organic Chemistry Lab 231 (Sec. 5) Dr. Bock/Daniel Miller Tiffany Raber 5 November 2012 Purpose: To prepare an alkene by an elimination reaction of an alcohol in the presence of sulfuric acid as a catalyst to produce a successful yield and desired results for the purity of the alkene. Introduction: The dehydration of an alcohol such as cyclohexanol is a useful technique for generating alkenes. The success of this reaction relies on a dehydration, such as the presence of a strong acid (sulfuric acid). Because this reaction is reversible, a fractional distillation is necessary to produce cyclohexene, water, and some impurities and a simple distillation is followed to further purify the product. [pic] (Fig. 1- Cyclohexanol dehydrated by sulfuric acid to produce cyclohexene) Procedure: 1. Mix five mL of Cyclohexanol and 2.5 mL of 9M sulfuric acid in a 25 mL flask. 2. Construct a fractional distillation apparatus (unpacked) while stirring the mixture and begin heating. a. Heat slow b. Do not heat over 90-100 degrees Celcius c. Ice water bath for distillate if desired 3. The distillate will be cloudy. Add anhydrous potassium carbonate in small amounts until it is no longer cloudy. Transfer to a 10 to 25 mL round bottom flask. 4. Construct a simple distillation making sure all tools are dry and clean. The flask should be pre-weighed. Drying tube must be connected to a vacuum adapter by a hose. a. Drying tube- clear, plastic tube filled with drying agent 5. After distillation, record the mass of the distillate and

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