Leonard, Lygo, 和 Procter:《進階實用有機化學》第二版
(第一章:簡介;第二章:安全、第三章:記錄保存、第四章:實驗室裝置、第八章:真空幫浦)
Before we get started in the lab, there are several chapters in the text that you must read first. Our time in the lab will be intense, but of limited duration, so it is important that you complete the readings on time. Not only is the reading essential to your success in 5.301, but it also will help in your development as an experimental chemist.
So, before you begin your experiments, take some time to read over the following chapters in Zubrick. This text was selected because it's easy to read and very practical. For more in-depth reading on these and related topics, we recommend the listed selections in the text by Leonard, Lygo, and Procter. A copy of this text will be available in the Reserve Book Room of the Science library. It is often difficult to fully grasp a laboratory concept by simply reading about it, but using the strategy of introductory reading, practicing in the lab, and post-lab review reading you will retain most of what we will cover in 5.301.
At the beginning of each lab period, there will be a short overview of that day's topic where Dr. Tabacco and your TAs will facilitate a discussion of the assigned reading and the actual lab experiment. You will also view relevant portions of The Digital Lab Techniques Manual to give you a visual representation of the important techniques. Time will be set aside to answer questions that you have from the readings.
The following list is the bulk of the reading for the course. There will also be additional reading during IAP, but this introductory reading is meant to familiarize you with the typical chemistry laboratory.
Zubrick, James. The Organic Chem Lab Survival Manual: A Student's Guide to Techniques. 6th ed.
(Chapters 1- Safety; 2- Notebooks; 4- Jointware; 6- Interesting Equipment; 9- Clean and Dry; 10- Drying Agents; 11- On Products; 15- Extraction and Washing; 18- Heat; 19- Clamps; 31- Instrumentation in the Lab)
Leonard, Lygo, and Procter. Advanced Practical Organic Chemistry. 2nd ed.
(Chapters 1- Introduction; 2- Safety; 3- Keeping Records; 4- Equipping the Lab; 8- Vacuum Pumps)
技術單元
Technique Modules
2.6的重要部份是涵蓋技術單元以致於組成課程的大部份。在此處的五大主題是轉移與萃取、再結晶純化、蒸餾純化、快速層析法純化和蛋白質測定與誤差分析。很重要的一點是實驗指南並不會提供你完成此實驗所需的資訊。許多重要的資訊你將會在預讀作業中找到,而有一些將會在實驗前簡短概述中討論。此三條路(課文、指南和討論)將會讓你準備好來對付技術單元中的實驗要點。
2-6節很重要的部份是技術清單。每一節的開始列出你在實驗期間將會遇到的技術。當你完成的技術單元,你將要回到技術核對清單並在清單上標記以證明你很熟練。如果你對特殊的技術仍然不熟練,那麼你將要多練習幾次直到你覺得有信心可以去運用於不同的實驗中。此了純化與操作技巧外,此節也將會介紹給你光譜技術像是核磁共振光譜(NMR)、紅外光譜(IR)、氣相層析法(GC)和紫外光-可見光(UV-Vis)光譜。
Sections 2–6 cover technique modules that make up the bulk of the class. The five topics included here are "Transfer and Extraction," "Purification by Crystallization," "Purification by Distillation," "Purification by Flash Column Chromatography," and "Protein Assays and Error Analysis." It is important to note that the manual does not contain all of the information that you will need to complete these experiments. Some important information will be found in your pre-lab reading, while the rest will be covered during the pre-lab discussion. This three-pronged approach (the texts, the manual, and the discussions) will prepare you to tackle the experiments outlined in the technique modules.
An important part of sections 2-6 is the techniques checklist. Each section begins with a list of techniques that you will encounter during the experiment. When you have completed a technique module, you should return to the techniques checklist and check off all of the techniques that you have mastered. If you are still uncomfortable with a specific skill then you should practice it until you feel confident that you could apply it in a different experiment. In addition to various purification and manipulation techniques, this section will also introduce you to spectroscopic techniques like nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, gas chromatography (GC), and ultraviolet-visible (UV-Vis) spectroscopy.
Note:
「CC」是指「合格的化學家」
"CC" refers to the "Competent Chemist" modules.
「EE」是指「有經驗的實驗者」
"EE" refers to the "Expert Experimentalist" modules.
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轉移和萃取技巧 Transfer and Extraction Techniques
- CC:乙基酯的精采冒險(PDF)
CC: Ethyl Ester's Excellent Adventure (PDF)
- EE:進入稀薄空氣(PDF)
EE: Into Thin Air (PDF)
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萃取: Zubrick Ch. 15, LLP Ch. 10 Extraction: Zubrick Ch. 15, LLP Ch. 10
萃取理論: Zubrick Ch. 37 Theory of Extraction: Zubrick Ch. 37
熔點的決定: Zubrick pp. 87-92 Melting Point Determination: Zubrick pp. 87-92
核磁共振光譜理論及操作: Zubrick Ch. 35, LLP Ch. 15.2 NMR Theory and Operation: Zubrick Ch. 35, LLP Ch. 15.2
額外的EE單元閱讀: Additional EE Module Reading:
- 空氣靈敏度技術: LLP Ch. 9
Air Sensitive Techniques: LLP Ch. 9
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數位實驗技巧單元: Digital Lab Techniques Manual:
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用再結晶來純化固體 Purification of Solids by Recrystallization
- CC:如何在結晶樟腦丸?(PDF)
CC: How do you Recrystallize a Mothball? (PDF)
- EE:單晶試驗(PDF)
EE: The Single-Crystal Shakedown (PDF)
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再結晶理論: Zubrick Ch. 13, LLP Ch. 11.2 Theory of Recrystallization: Zubrick Ch. 13, LLP Ch. 11.2
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數位實驗技巧單元: Digital Lab Techniques Manual:
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用蒸餾來純化液體 Purification of Liquids by Distillation
- CC: 桃子如何到香蕉裡面的?(PDF)
CC: How did the Peach Get in the Banana? (PDF)
- EE:高海拔處的烹煮法是什麼?(PDF)
EE: What’s with Those High-Altitude Recipes? (PDF)
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蒸餾理論: Zubrick Ch. 36, LLP Theory of Distillation: Zubrick Ch. 36, LLP Ch. 11.3
蒸餾器皿與如何架設裝置: Zubrick Ch. 20 Distillation Glassware and How to Set it Up: Zubrick Ch. 20
氣相層析儀的使用: Zubrick Ch. 32 Use of the GC: Zubrick Ch. 32
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用快速層析分離的純化 Purification by Flash Column Chromatography
- CC: 看到的不一定是真的(PDF)
CC: Looks can be Deceiving (PDF)
- EE:設定流速(PDF)
EE: Setting the Pace (PDF)
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管柱層析儀理論: Zubrick Ch. 27 Theory of Column Chromatography: Zubrick Ch. 27
薄層分析法-極性/溶劑系統: TLC - Polarity/Solvent Systems: Zubrick Ch. 28, LLP Ch. 9.3.1
準備一矽膠管柱: Zubrick Ch. 29, LLP Ch. 11.6 Setting up a Silica Gel Column: Zubrick Ch. 29, LLP Ch. 11.6
適用於管註層析法的最初的產物混合物 Applying Crude Mixtures to the Column
跑快速層析分離管柱 Running a Flash Column
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數位實驗技巧單元: Digital Lab Techniques Manual
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蛋白質化驗與誤差分析 Protein Assays and Error Analysis
- CC: 乳牛的心臟中有什麼?(PDF)
CC: What's in a Cow's Heart Anyway? (PDF)
- EE: 一個像鐵一樣強壯的心臟(PDF)
EE: A Heart as Strong as Iron (PDF)
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創新研究計畫(PDF)
Original Research Project (PDF)
在實驗指南的第七部份中,這些簡短的實驗的將會介紹給你一些實際的創新研究並示其刺激性。
Found in section seven of the Lab Manual, this brief set of experiments will introduce you to some of the realities and excitement of performing original research.
技術簡介
Technique Guides
在實驗指南的第八部份中,這些簡介將會提供你一些在化學實驗室更常碰到的技術並一步一步的指導你。
Found in section eight of the Lab Manual, these guides will provide you with step-by-step instructions for some of the more common techniques encountered in a chemistry laboratory.
| 8.1 |
傅立葉轉換核磁共振光譜樣品準備簡介(PDF) FT-NMR Sample Preparation Guide (PDF) |
| 8.2 |
氣相層析儀樣品準備簡介(PDF) GC Sample Preparation Guide (PDF) |
| 8.3 |
薄層層析法(TLC)簡介(PDF) Thin Layer Chromatography (TLC) Guide (PDF) |
| 8.4 |
萃取與沖洗簡介(PDF) Extraction and Washing Guide (PDF) |
| 8.5 |
無空氣技術簡介(PDF) No-Air Techniques Guide (PDF) |
| 8.6 |
兩溶劑再結晶簡介(PDF) Two-Solvent Recrystallization Guide (PDF) |
| 8.7 |
養單晶簡介(PDF) Guide to Growing a Single Crystal (PDF) |
| 8.8 |
蒸餾簡介(PDF) Distillation Guide (PDF) |
| 8.9 |
快速層析分離簡介(PDF) Flash Column Chromatography Guide (PDF) |
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講義
Handouts
光譜技術介紹(PDF)
Introduction to Spectroscopic Techniques (PDF)
數位實驗技巧指南(PDF)
The Digital Lab Techniques Manual (PDF)
致謝
Acknowledgements
此課程的實驗指南和材料是由Katherine J. Franz and Kevin M. Shea 和助理教授Rick L. Danheiser 和Timothy M. Swager。材料則由J. Haseltine, Kevin M.Shea和Sarah A. Tabacco所校訂。
The laboratory manual and materials for this course were prepared by Katherine J. Franz and Kevin M. Shea with the assistance of Professors Rick L. Danheiser and, and Timothy M. Swager. Materials have been revised by J. Haseltine, Kevin M.Shea, and Sarah A. Tabacco.