lab 6

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Lab SD: Simple Distillation and Boiling Point Analysis Purpose In this experiment, you will familiarize yourself with the theory of distillation by purifying an unknown organic compound by simple microscale distillation. You will the identify the unknown compound using boiling point and density measurements. Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.1 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
Simple Distillation Background Background Distillation is one of the oldest and most common methods for the purification and identification of organic liquids. It is a physical process used to separate chemicals from a mixture by the difference in how easily they vaporize. As the mixture is heated, the temperature rises until it reaches the temperature of the lowest boiling substanceinthemixture, whiletheothercomponentsof themixtureremainintheiroriginalphaseinthemixture. The resultant hot vapor passes into a condenser and is converted to the liquid, which is then collected in a receiver Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.2 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD. Learning Objectives Set up and perform a simple microscale distillation. Use boiling point and density in identification of an organic compound. Laboratory Skills Perform a simple distillation. Determine a boiling point. Equipment Reflux condenser Joint grease Boiling chips 10 mL round bottom flask Clamps Ring stand Water hoses Rubber O-rings Plastic caps Aluminum block Hot plate/stirrer Hickman still pH paper Thermometer Glass pipet 3 mL conical vial Syringe Centrifuge tube Chemicals Unknown organic compound DI water References: 1. Multiscale OperationalOrganicChemistry, by JohnW. Lehman, custom edition, Prentice Hall Publishing, New Jersey, 2009; pp. 679-691. 2. Pavia, D.; Lampman, G.; Kriz, G.; Engel, R., Organic Laboratory Techniques , Saunders College Publishing, New York 1990; pp. 638-651.
Simple Distillation flask. The other components of the mixture remain in their original phase until the most volatile substance has all boiled off. Only then does the temperature of the gas phase rises again until it reaches the boiling point of a second component in the mixture, and so on. The boiling point of a substance—determined by distillation—is a useful physical property for the characterization of pure compounds. At any given temperature a liquid is in equilibrium with its vapor. This equilibrium is described by the vapor pressure of the liquid. The vapor pressure is the pressure that the molecules at the surface of the liquid exert against the external pressure, which is usually the atmospheric pressure. The vapor pressure is a very sensitive function of temperature. It does not increase linearly but in fact increases exponentially with temperature. The vapor pressure of a substance roughly doubles for every increase in 10 C. When the vapor pressure of the liquid equals the applied pressure, the liquid boils. Thus, the boiling point of a liquid is the temperature at which the vapor pressure equals the applied pressure. The normal boiling point of a liquid is the temperature at which the vapor pressure of a liquid equals atmospheric pressure (1 atm). The boiling point of a liquid is a measure of its volatility. Simple distillation involves a single equilibration between the liquid and vapor. This distillation is referred to as involving one theoretical plate and is frequently in the organic chemistry teaching labs, when the liquid is relatively pure to begin with (e.g., no more than 10% liquid contaminants). Essentially, a pure material is separated from a non-volatile or from a solid contaminant. The liquid is contaminated by a liquid with a boiling point that differs by at least 70 C. Theprincipleof fractionaldistillation isbasedontheestablishmentof alargenumberof theoreticalvaporizationcondensation cycles (theoretical plates): the apparatus of a simple distillation is modified by inserting a fractionating column between the distillation flask and the distillation head, The fractionating column provides a large surface area in which the initial distillate is redistilled and condensed again. This process continues as the vapors rise up the column until the vapors finally make it into the condenser. These vapors and the final distillate will contain a greater percentage of the lower boiling liquid. Continuous repetition of re-distillation process in fractional distillation gives good separation of the volatile liquid components. Microscale Simple Distillation The complete micro scale simple distillation setup is shown in Figure SD.1 and consists of a round-bottom flask containing the liquid and 2 – 3 boiling stones, attached to the bottom joint of a Hickman still head (Figure SD.1A). A condenser is attached to the top joint. A thermometer can be suspended down the middle in order to record the distilling temperature, with the bottom of the thermometer in the lower part of the Hickman head just below the circular well (Figure SD.1C). Thevaporof theheatedliquid risesupwardandiscooled andcondenseson eitherthe insidewallsof theHickman head or on the walls of the condenser. The condensate then collects in the circular well at the bottom of the still. The well Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.3 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
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Simple Distillation can contain as much as 2 mL of liquid. The Hickman still we use has a side port to help with the distillate’s removal. Distillate can later be removed with the help of a Pasteur pipet after opening the port (Figure SD.1B). Once removed, the liquid is transferred to a smaller vial and capped with a Teflon-sealed cap. By recording the boiling point and the density of the collected liquid you can identify the liquid after comparing it to a known sample. Figure SD.1: (A) shows the Hickman head with the side port closed. (B) shows the Hickman head with the side port open so it can be accessed with a glass pipet. (C) shows the position of the thermometer in the Hickman head. The image on the right shows the distillation setup. Procedure Safety Precautions Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.4 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
Simple Distillation Full-sleeved shirts, full pants and shoes (covering all areas of foot) must be worn at all times. Wear splash-proof goggles at all times. Gloves must be worn when handling chemicals. All organic compounds are extremely flammable. Organic compounds can be toxic they may target organs like liver kidneys and neural cells. Be careful not to breathe your product or get it on your skin. Please review SDS notes before lab. All chemicals should be handled in the hood to avoid inhalation. No eating and drinking allowed in the lab. Wash your hands after handling the reagents. The aluminum block, hot plate and your glassware can become very hot. Please use caution as they can cause severe burns. If any chemical gets on your skin wash the area with tap water for at least 15 minutes. Check with TA if further treatment is necessary. All liquid and solid chemical waste should be discarded in the waste containers located in the dispensing hoods. No flames should be used in the laboratory. Experimental: Distillation Setup 1. Lightly grease the tapering ground glass joint of a reflux (jacketed) condenser. Too much grease will cause problems. Show to your TA before proceeding. 2. Add approximately 5 mL of the unknown organic assigned by your TA to a 10 mL round bottom flask (this is your distillation flask). 3. Add 2-3 boiling chips to the distillation flask and securely clamp the neck of the flask to a ring stand. Make sure the clamp is secure and clamped below the lip of the neck of the distillation flask. 4. Attach the Hickman still to your distillation flask, the side port of the still should be properly capped and the ground glassware joints are lightly greased. 5. Connect water hoses to the greased reflux (jacketed) condenser. 6. Attach the condenser to your distillation flask (make certain that your ground glassware joints are lightly greased). Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.5 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
Simple Distillation 7. Secure all glassware joint connections with rubber O-rings and plastic caps. 8. Connect the water hose from the lower nozzle of the reflux condenser (See ?? ) to a faucet. The water hose from the upper nozzle (outlet) should be placed in the sink at the back of the hood. 9. Turn on the faucet valve slowly, until a gentle stream of water flows through the reflux condenser, do not start heating. 10. Place an aluminum block with the slight depression facing up on a hot plate stirrer. 11. Lower the 10 mL distillation flask into the heating well. 12. Insulate the top of the distillation flask and lower part of the Hickman still by loosely wrapping with aluminum foil. 13. Make sure that water is gently flowing through the condenser before you begin heating. 14. Suspend a thermometer (use a small O-ring or a clamp) down the middle of the condenser. The bottom of the thermometer should be in the lower part of the Hickman still head (see ?? C) just below the circular well. Safety Precaution The top of the top of the condenser should be open to the air and not capped or sealed. Have your TA check your setup before you start heating. Distillation 15. Start heating with your heating plate dial set to 30% power. You can increase this setting later after consulting with your TA. 16. Using a glass pipet collect 3 distillate fractions during the distillation (from the side port, see ?? B): The liquid (the forerun) which is collected before the temperature stabilizes (distillate fraction 1). The liquid which is collected after the temperature has stabilized (distillate fraction 2). When about 0.5 mL of impure liquid remains in the distillation flask (distillate fraction 3). Record the temperature when each fraction is collected. Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.6 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
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Simple Distillation 17. Record the boiling point range as when the solvent begins to boil and collect in the well to the temperature once it stabilizes again. 18. After collecting your last fraction, remove the flask from the Aluminum block and allow it to cool. Do not distill to dryness. As the distillation apparatus cools, perform the other tests on your unknown. Density and Solubility Test 19. Transfer 0.25 ml (syringe) of distillate fractions B to a pre-weighed , clean, and dry 3 mL conical vial and determine its density. 20. Add 0.5 mL of distillate B to a clean and dry centrifuge tube to perform the solubility test. 21. Add 1 mL of DI water to this tube. Cap and shake the tube a few times. Remember to vent. 22. Remove the cap and place the tube in a beaker and allow the mixture to settle for approximately 2 minutes. 23. One layer means the unknown organic is miscible with water (see Table SD.1). Two layers means unknown organic is immiscible with water. 24. Record your observations (one layer or two layers). Comparison to Known Organic Compound 25. Carefully disassemble the cooled distillation apparatus. Do not wash glassware with water. In the next step, use the condenser without cleaning. 26. Consult Table SD.1 and select one of the organic compounds whose data (boiling point, density and solubility) is nearest (boiling point will not be exactly the same) to your unknown’s data. Due to the differences in your technique and experimental errors the observed data of your unknown may not match the literature value of any compound. Table SD.1: Possible Unknown Organic Compounds Substance Solubility in Water Literature Boiling Point ( C) Literature Density (g/mL) Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.7 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
Simple Distillation Cyclohexane Poor - Miscible 80-81 0.779 Methyl Alcohol Very Good - Miscible 64-66 0.792 Hexane Poor - Immiscible 68-69 0.654 Ethyl Acetate Poor - Immiscible 76-78 0.902 Ethyl Alcohol Very Good - Immiscible 77-79 0.789 27. Perform the solubility test and determine the density of the organic compound you believe to be your unknown. 28. Determine the boiling point of the organic compound you believe to be your unknown by attaching a reflux condenser to a clean 3 mL conical flask. You do not need a Hickman still. Suspend a thermometer (use the same thermometer) down the middle of the condenser. The bottom of the thermometer should be slightly above the liquid in the flask. 29. When you have completed all the tests and recorded the data, ask your TA if you can start cleaning up. Cleanup 30. Clean up your bench and hood area. All the chemicals should be discarded in the appropriate waste container. You do not need to clean your glassware with water. 31. Wipe off the excess grease from the glassware. Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.8 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.
Introduction Draw the chemical structures for ethyl acetate, acetone, methyl alcohol, cyclohexane, ethyl alcohol, and n - hexane. Experimental Inashortparagraph, describetheset-upof thedistillationapparatusandtheprocessof distillation, including what the sample was doing at each step. Simple Distillation Report Sheet Results Unknown Compound Assigned: A / C / M / F / K / O Report Table SD.1: Distillation Temperatures of Unknown Distillate fraction Temp when collection started ( C) 1 Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.1 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD. Report Sheet: Simple Distillation Name: Section: Date: 2 3
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Organic compound assumed to be unknown (from Table SD.1): Report Table SD.2: Characterization of Unknown and Assumed Compound Data indicates that unknown organic ( A / C / M / F / K / O ) is: Simple Distillation Report Sheet Discussion Justify your identification of your unknown based on its behavior in the distillation and the characterization tests. Explain the difference in boiling point between your unknown and the other solvents. For example, you can discuss hydrogen bonding, polarity, molecular weight, whether the structure is branched or linear, etc. Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.2 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD. Unknown-Fraction 2 Known-Assumed compound Temp. at boil start ( C) Temp. at boil end ( C) Vol. for density (mL) Mass of volume (g) Density (g/mL) Vol. for solubility (mL) Vol. of water (mL) Number of layers Solubility GOOD/POOR GOOD/POOR
Explain the difference in solubility of your unknown in water compared to the other solvents. Catalyst Education OER Labs are licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 license. SD.3 To access our full list of experiments visit https://links.labflow.com/OER. Lab Version SD.