麻省理工学院：《有机化学基本实验操作技巧》教学资源（讲义）How did the Peach Get in the Banana

and riskfor the implementation of such safety procedures and measures. MrT shall haven orris for the content or implementation of a y of the material preseated Legal Notices 3. Purification of liquids by Distillation 3. 1. Competent Chemist Rating: "How Did the Peach Get in the Banana? Techniques Checklist Setting up distillation glassware correctly Performing atmospheric pressure distillations Using Gas Chromatography(GC)to analyze samples u Pre-lab Discussion and required reading: Theory of distillation: Zubrick Ch. 36, LLP Ch. 11.3 Distillation glassware and how to set it up: Zubrick Ch. 20 Use of the gc: Zubrick ch 32 E . quipment Round-bottomed flasks(1x25-mL, lx50-mL) Magnetic stir bar Distillation kit(distillation head) Ground glass thermometer Glass wool and aluminum foil (optional) Heating mantle(w/ sand) and variac To purify a mixture of two liquids using distillation. Experiment Outline: You will receive a vial containing 11. 20 g of a mixture of 2 compounds whose boiling points differ by about 40C(See possible Analyze the mixture using the gC -see GC Sample preparation and GC Operation guides Perform atmospheric pressure distillation-see Distillation Guide Prepare a GC sample of your purified low-boiling product Obtain a mass and a gas chromatogram of your purified low-boiling compound

3. Purification of Liquids by Distillation 3.1. Competent Chemist Rating: “How Did the Peach Get in the Banana?” Techniques Checklist: • Setting up distillation glassware correctly ❑ • Performing atmospheric pressure distillations ❑ • Using Gas Chromatography (GC) to analyze samples ❑ Pre-lab Discussion and Required Reading: • Theory of distillation: Zubrick Ch. 36, LLP Ch. 11.3 • Distillation glassware and how to set it up: Zubrick Ch. 20 • Use of the GC: Zubrick Ch. 32 Equipment: • Round-bottomed flasks (1x25-mL, 1x50-mL) • Magnetic stir bar • Distillation kit (distillation head) • Ground glass thermometer • Keck clips • Glass wool and aluminum foil (optional) • Heating mantle (w/ sand) and variac Goal: • To purify a mixture of two liquids using distillation. Experiment Outline: • You will receive a vial containing 11.20 g of a mixture of 2 compounds whose boiling points differ by about 40 °C (See possible compounds below.). • Analyze the mixture using the GC - see GC Sample Preparation and GC Operation Guides. • Perform atmospheric pressure distillation - see Distillation Guide. • Prepare a GC sample of your purified low-boiling product. • Obtain a mass and a gas chromatogram of your purified low-boiling compound. 24 WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. WARNING NOTICE: The experiments described in these materials are potentially hazardous and require a high level ofsafety training, special facilities and equipment, and supervision by appropriate individuals. You bear the sole responsibility, liability, and risk for the implementation of such safety procedures and measures. MIT shall have no responsibility, liability, or risk for the content or implementation of any of the material presented. Legal Notices

H3C Ethyl Isobutyrate(Peach) Isoamyl Acetate(Banana) BP112-113°C 3-Dimethylpyrazine Ethyl Heptanoate BP188-189°C) Helpful Hints Make sure all of your joints are lightly greased and sealed well. Otherwise, you ill lose your product into the atmosphere Insulate your distillation head with cotton and foil to speed things up Do not heat your mixture too fast, or your entire sample will end up in your Be aware that the temperature reading on the thermometer may not correlate accurately with the boiling point of the distilling liquid Results: To obtain your CC Rating" in Purification of Liquids by Distillation, you must obtain at least 7.00 g of the low-boiling material that is 92% pure or better as determined using GC analysis. You must also correctly identify the two components of your mixture. Think boiling points and smell

CH3 O CH3 O CH3 H3C H3C O CH3 O Ethyl Isobutyrate (Peach) Isoamyl Acetate (Banana) (BP 112–113 °C) (BP 142–143 °C) N CH3 O CH3 N CH3 H3C O 2,3-Dimethylpyrazine Ethyl Heptanoate (BP 156 °C) (BP 188–189 °C) Helpful Hints: • Make sure all of your joints are lightly greased and sealed well. Otherwise, you will lose your product into the atmosphere. • Insulate your distillation head with cotton and foil to speed things up. • Do not heat your mixture too fast, or your entire sample will end up in your collection flask. • Be aware that the temperature reading on the thermometer may not correlate accurately with the boiling point of the distilling liquid. Results: • To obtain your "CC Rating" in Purification of Liquids by Distillation, you must obtain at least 7.00 g of the low-boiling material that is 92% pure or better as determined using GC analysis. You must also correctly identify the two components of your mixture. Think boiling points and smell! 25