09 Cyclohexene

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CUNY College of Staten Island *

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250

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Chemistry

Date

Jan 9, 2024

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docx

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3

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Cyclohexene 1. Purpose (5pts) The purpose of this experiment was to use cyclohexanol in a reaction in order to collect cyclohexene. 2. Balanced equation (5pts) Cyclohexanol 3. Procedure (20pts) 3.1) Place 10 mL of cyclohexanol in a 50 mL round bottom flask. Then add 2.5 mL of 85% phosphoric acid and mix thoroughly. Begin heating and continue setting up the apparatus as shown in the diagram. When 10mL of cyclohexanol and 2.55mL of 85% phosphoric acid were mixed and heated the solution resulted in a clear liquid substance. 3.2) Distill into an ice-cooled test tube until about 5 mL of residue remains in the flask. 7mL distillate should be collected. The distillate was 7mL clear and cloudy. 3.3) Allow the residue to cool for 3 minutes after removing the heat. When cooled the residue was approx. 5mL and was a yellow-brown color. 3.4) Add 10 mL of toluene to the top of the column using a long-stemmed funnel. Distill 5 mL more of the distillate. Discard the residue into the proper waste container and clean your 50 mL round bottom flask. When 10mL of toluene was added the residue remained yellow and the distillate was clear.
3.5) Transfer the distillate in the test tube into a 125 mL separatory funnel. Rinse the tube with 5 mL of saturated sodium chloride and add to the separatory funnel. Add an additional 8 mL of saturated sodium chloride into the separatory funnel. When sodium chloride was added the mixture was clear. 3.6) Shake, vent, and allow the layers to separate. Drain the lower water layer and discard. When shaken and vented two layers were formed and both layers were clear. One layer was cloudier than the other. 3.7) Add 2g of sodium sulfate anhydrous to a dry 125 mL Erlenmeyer flask then pour what was the upper layer out from the top of the funnel into the flask. Cover the flask with a beaker and allow it stands for 10 minutes. Ensure that your 50 mL round bottom flask is dry. The sodium sulfate was added and when it stood for 10 minutes the solution was clear. 3.8) Decant the dried extract into a clean flask. The solution was clear, and 17mL of the solution was collected. 3.9) Calculate the percent yield and theoretical yield. (Outlets were not working, data is from a classmate) 4. Result and Explanation 4.1) Yield? high or low? (10pts) The yield of the mixture was higher. 4.2) Reasons (15pts) 1) (5pts) One reason it could have been higher is because toluene may have remained in the mixture.
2) (5pts) The mixture could not have been heated enough. 3) (5pts) There were too many different solvents added. Post-lab Assignment 1. Why should the test tube which collects cyclohexene be immersed in an ice bath? The test tube collecting cyclohexene should be immersed in an ice bath to facilitate the condensation of the vaporized cyclohexene back into a liquid state. By immersing the collection test tube in an ice bath, the vapor pressure of the cyclohexene is reduced, causing it to condense and collect in the bottom of the test tube as a liquid. This also minimizes the loss of cyclohexene due to evaporation. 2. Could sulfuric acid or hydrochloric acid be used instead of phosphoric acid in this experiment? Why? Sulfuric acid and hydrochloric acid can also catalyze the dehydration of alcohols, but they are typically more reactive and can lead to side reactions. Sulfuric acid or hydrochloric acid could be used as an alternative to phosphoric acid in the dehydration of cyclohexanol, they may not provide the same level of selectivity and efficiency as phosphoric acid.
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