1-3: Performing a Distillation Distillation is a separation technique utilized by organic chemists. A distillation apparatus...
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1-3: Performing a Distillation Distillation is a separation technique utilized by organic chemists. A distillation apparatus separates liquid compounds based on boiling points. The boiling point of each compound is determined by the intermolecular forces that exist in a solution of the compound. In a standard distillation apparatus, the mixture of liquid compounds is held within a round bottom flask known as the distillation flask. A thermometer is used to measure the temperature of the liquid in the distillation flask, and the entrance point for the thermometer is sealed. The distillation flask is also connected to a condenser at a joint. The remaining open end of the condenser is connected to a second flask called the collection flask. Heat is applied to the distillation flask and the temperature is monitored via the thermometer. As the boiling point of one of the compounds is reached, the compound is vaporized and travels into the condenser. Cold water is run through the condenser, which causes the vapors to cool and condense on the inside of the condenser. The condensed vapors drip out of the condenser and into the collection flask. The collected liquid, called the distillate, is now separated from the other compounds in the distillation flask. Note that this is a sealed system and an inert gas must also be attached to provide pressure relief and an inert environment for the distillate. Thermometer Distillation Flask Condenser Collection Flask In this assignment, you will be guided through the steps of a Friedel-Crafts reaction as a demonstration of how to use a distillation apparatus as a tool to separate products. This assignment will also serve as a tutorial to teach you how to utilize the various parts of the organic simulation that will be used in later assignments. 1. Start Virtual ChemLab Organic and select Performing a Distillation from the list of assignments. The lab will open in the Synthesis laboratory, and you should see a lab bench containing reagents on the back of the bench, aqueous reagents on the right, an equipment rack containing necessary laboratory equipment, a red disposal bucket for cleaning up the lab, and the organic stockroom in the back. Other pieces of laboratory equipment will be used in other assignments. 2. You will find a round bottom flask located on the stockroom counter. Select the starting materials for the reaction by first clicking on the bottle containing benzaldehyde and dragging and dropping the syringe on the mouth of the flask. Now do the same for the other reactant-acetyl chloride and for the solvent-ether. Note the bottle labels are small, but you can see the full name and structure of each starting material by hovering over the bottle. Now click on the flask and drag it to the stir plate on the lab bench. It should snap into place when you are at the right location. 3. The round bottom flask containing the starting material should now be on the stir plate. The starting materials should be listed on the chalkboard, and hovering over a listed starting material will display its structure on the chalkboard. Help on using Virtual ChemLab Organic can be found by clicking on the bell on the stockroom counter. 4. In order to perform the reaction, aluminum chloride (AICI,) must be added. This is done by clicking on the Aluminum Trichloride bottle on the back of the lab bench and dragging the spatula to the round bottom flask. The reagent can also be added by double-clicking on the bottle. The chalkboard should now show that the reagent has been added to the reaction mixture. 5. Before the reaction can be started, we must be able to heat the flask so the reaction can proceed at a suitable rate. This is done by adding a heating mantle to heat the reaction mixture, adding a condenser so the mixture can be refluxed, and then adding nitrogen gas to maintain an inert atmosphere and to prevent pressure buildup. Click on the Heating Mantle and drag it to the round bottom flask to place it on the stir plate. Now click on the Condenser from the equipment rack and drag it on top of the round bottom flask. Finally, click on the N; Gas hose to the right of the stir plate and drag and drop it on top of the condenser. Now click on the Stir Plate button to start the reaction. You should see the reaction mixture stirring in the round bottom flask. 6. Allow the reaction to proceed until the product begins to form, but do not let it go to completion. A reaction time of 3 minutes is sufficient. The reaction will proceed in real time. However, time can be sped up. The three blue buttons beneath the LED clock display can advance the time in 1 min, 10 min, and 1 hr intervals. This reaction occurs fairly quickly, so only advance the time in 1 min intervals (if at all). You will be able to monitor the progress of the reaction either by running TLC plates, by looking at the compounds on the blackboard, or both. The blackboard updates as the reaction proceeds, displaying the names of all compounds in the flask. 7. After 3 minutes, the reaction mixture will contain both product and starting materials. Perform a separatory funnel extraction (see activity 1-2: Performing a Separatory Funnel Extraction). Add H₂O by clicking on the large H₂O container and dragging it to the separatory funnel. The separatory funnel should have two distinct layers of liquid. Remove and keep the organic layer, which contains your product. Do this by clicking on and dragging the organic layer to the cork ring, where it will be placed in a new round bottom flask. Notice that the organic layer contains the product and what remains of one of the starting materials. What is the product that is in the organic layer? What is the starting material that is in the organic layer? 8. The aqueous layer in the separatory funnel can be discarded in the red bin, and the funnel can be returned to the equipment rack. Put the round bottom flask with the organic layer onto the stir plate. Bring the Distillation apparatus over from the equipment rack by clicking and dragging, placing it on top of the round bottom flask on the stir plate. It should snap in place. Hovering over the thermometer will show you the temperature of the apparatus. You can also hover over the collection flask, which will be filled with distilled compounds as you carry out the distillation. 9. Attach the N₂ Gas hose to the distillation apparatus to prevent pressure buildup. The distillation is started by clicking on the Stir Plate button. The apparatus takes 5-10 minutes to reach the boiling point of the compound with the lowest boiling point. You can monitor the temperature by hovering over the thermometer. 10. The boiling point of one of the products is around 178 °C. As the distillation apparatus reaches this temperature, slowly advance the time until liquid begins to collect in the collection flask. Which of the compounds has this lower boiling point and therefore begins to distill first (we will refer to this compound as Compound 1)? 11. By hovering over the distillation flask, you will notice that some of Compound 1 remains mixed with the other compound. Continue to advance the time until all of Compound 1 is in the collection flask and none remains in the distillation flask. What is the compound remaining in the distillation flask (Compound 2)? 12. Draw the structures of Compounds 1 and 2. 13. Intermolecular forces define the boiling points of compounds. What type of intermolecular forces exist for Compounds 1 and 2?_ Based on what you now know about the boiling points of Compounds 1 and 2, in which are intermolecular forces stronger? Why? Distillation can be used to separate products from products, starting materials from products, or solvents from products through boiling point differences. Some lab activities in Virtual ChemLab Organic will require you to use the principles of distillation learned here to make necessary separations. 1-3: Performing a Distillation Distillation is a separation technique utilized by organic chemists. A distillation apparatus separates liquid compounds based on boiling points. The boiling point of each compound is determined by the intermolecular forces that exist in a solution of the compound. In a standard distillation apparatus, the mixture of liquid compounds is held within a round bottom flask known as the distillation flask. A thermometer is used to measure the temperature of the liquid in the distillation flask, and the entrance point for the thermometer is sealed. The distillation flask is also connected to a condenser at a joint. The remaining open end of the condenser is connected to a second flask called the collection flask. Heat is applied to the distillation flask and the temperature is monitored via the thermometer. As the boiling point of one of the compounds is reached, the compound is vaporized and travels into the condenser. Cold water is run through the condenser, which causes the vapors to cool and condense on the inside of the condenser. The condensed vapors drip out of the condenser and into the collection flask. The collected liquid, called the distillate, is now separated from the other compounds in the distillation flask. Note that this is a sealed system and an inert gas must also be attached to provide pressure relief and an inert environment for the distillate. Thermometer Distillation Flask Condenser Collection Flask In this assignment, you will be guided through the steps of a Friedel-Crafts reaction as a demonstration of how to use a distillation apparatus as a tool to separate products. This assignment will also serve as a tutorial to teach you how to utilize the various parts of the organic simulation that will be used in later assignments. 1. Start Virtual ChemLab Organic and select Performing a Distillation from the list of assignments. The lab will open in the Synthesis laboratory, and you should see a lab bench containing reagents on the back of the bench, aqueous reagents on the right, an equipment rack containing necessary laboratory equipment, a red disposal bucket for cleaning up the lab, and the organic stockroom in the back. Other pieces of laboratory equipment will be used in other assignments. 2. You will find a round bottom flask located on the stockroom counter. Select the starting materials for the reaction by first clicking on the bottle containing benzaldehyde and dragging and dropping the syringe on the mouth of the flask. Now do the same for the other reactant-acetyl chloride and for the solvent-ether. Note the bottle labels are small, but you can see the full name and structure of each starting material by hovering over the bottle. Now click on the flask and drag it to the stir plate on the lab bench. It should snap into place when you are at the right location. 3. The round bottom flask containing the starting material should now be on the stir plate. The starting materials should be listed on the chalkboard, and hovering over a listed starting material will display its structure on the chalkboard. Help on using Virtual ChemLab Organic can be found by clicking on the bell on the stockroom counter. 4. In order to perform the reaction, aluminum chloride (AICI,) must be added. This is done by clicking on the Aluminum Trichloride bottle on the back of the lab bench and dragging the spatula to the round bottom flask. The reagent can also be added by double-clicking on the bottle. The chalkboard should now show that the reagent has been added to the reaction mixture. 5. Before the reaction can be started, we must be able to heat the flask so the reaction can proceed at a suitable rate. This is done by adding a heating mantle to heat the reaction mixture, adding a condenser so the mixture can be refluxed, and then adding nitrogen gas to maintain an inert atmosphere and to prevent pressure buildup. Click on the Heating Mantle and drag it to the round bottom flask to place it on the stir plate. Now click on the Condenser from the equipment rack and drag it on top of the round bottom flask. Finally, click on the N; Gas hose to the right of the stir plate and drag and drop it on top of the condenser. Now click on the Stir Plate button to start the reaction. You should see the reaction mixture stirring in the round bottom flask. 6. Allow the reaction to proceed until the product begins to form, but do not let it go to completion. A reaction time of 3 minutes is sufficient. The reaction will proceed in real time. However, time can be sped up. The three blue buttons beneath the LED clock display can advance the time in 1 min, 10 min, and 1 hr intervals. This reaction occurs fairly quickly, so only advance the time in 1 min intervals (if at all). You will be able to monitor the progress of the reaction either by running TLC plates, by looking at the compounds on the blackboard, or both. The blackboard updates as the reaction proceeds, displaying the names of all compounds in the flask. 7. After 3 minutes, the reaction mixture will contain both product and starting materials. Perform a separatory funnel extraction (see activity 1-2: Performing a Separatory Funnel Extraction). Add H₂O by clicking on the large H₂O container and dragging it to the separatory funnel. The separatory funnel should have two distinct layers of liquid. Remove and keep the organic layer, which contains your product. Do this by clicking on and dragging the organic layer to the cork ring, where it will be placed in a new round bottom flask. Notice that the organic layer contains the product and what remains of one of the starting materials. What is the product that is in the organic layer? What is the starting material that is in the organic layer? 8. The aqueous layer in the separatory funnel can be discarded in the red bin, and the funnel can be returned to the equipment rack. Put the round bottom flask with the organic layer onto the stir plate. Bring the Distillation apparatus over from the equipment rack by clicking and dragging, placing it on top of the round bottom flask on the stir plate. It should snap in place. Hovering over the thermometer will show you the temperature of the apparatus. You can also hover over the collection flask, which will be filled with distilled compounds as you carry out the distillation. 9. Attach the N₂ Gas hose to the distillation apparatus to prevent pressure buildup. The distillation is started by clicking on the Stir Plate button. The apparatus takes 5-10 minutes to reach the boiling point of the compound with the lowest boiling point. You can monitor the temperature by hovering over the thermometer. 10. The boiling point of one of the products is around 178 °C. As the distillation apparatus reaches this temperature, slowly advance the time until liquid begins to collect in the collection flask. Which of the compounds has this lower boiling point and therefore begins to distill first (we will refer to this compound as Compound 1)? 11. By hovering over the distillation flask, you will notice that some of Compound 1 remains mixed with the other compound. Continue to advance the time until all of Compound 1 is in the collection flask and none remains in the distillation flask. What is the compound remaining in the distillation flask (Compound 2)? 12. Draw the structures of Compounds 1 and 2. 13. Intermolecular forces define the boiling points of compounds. What type of intermolecular forces exist for Compounds 1 and 2?_ Based on what you now know about the boiling points of Compounds 1 and 2, in which are intermolecular forces stronger? Why? Distillation can be used to separate products from products, starting materials from products, or solvents from products through boiling point differences. Some lab activities in Virtual ChemLab Organic will require you to use the principles of distillation learned here to make necessary separations.
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SOLUTION Compound 1 Toluene Compound 2 Compound 3 Ethee Product is Acetyl chloride C83 ROR 4methy... View the full answer
Related Book For
Physics
ISBN: 978-0077339685
2nd edition
Authors: Alan Giambattista, Betty Richardson, Robert Richardson
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