1) The textbook: “Organic Chemistry Laboratory, Standard and Microscale Experiments, third ed.” by C. E. Bell, Jr., Allen Clark, And Douglas Taber; Harcourt College Publishing, 2001.

2) A laboratory notebook which is permanently bound, has serially numbered pages, and which allows you to make a removable carbon copy which can be turned in for grading.

3) A laboratory coat - knee-length and long-sleeved.

4) Safety goggles (NOT SAFETY GLASSES). The laboratory coat and goggles must be worn at all times anyone in the laboratory is doing experimental work. They may be purchased in the chemistry department. (Note: No open-toed shoes are allowed in the laboratory at any time!)

5) A STRONG, RELIABLE lock for your laboratory drawer. Lock your drawer whenever you leave your bench, even if you are only walking across the room! Lock your drawer at the end of every lab period. You are responsible for any broken, missing, or stolen glassware and equipment.

NOTE: The following may be subject to revision. It is the responsibility of the student to make note of any such revision when given by the TA.

Jan 13-18	Orientation, check-in. Wash glassware and watch films on safety, using standard equipment and distillation.
Jan 20	Martin Luther King Day - No Lab.
Jan 21-27	Remember to bring your lab coat, goggles, lab manual, lab notebook, and lock. Prelaboratory preparation: Read Chapters 1 (Introduction), 2 (Melting Points), and 5 (Distillation). Answer in your laboratory notebook Prelaboratory Questions 1-5, p. 22 and 1-5, p. 58. EXPERIMENTS: Chapter 2 - Using the techniques described in parts A, B, and C, you will: 1. Calibrate a thermometer by determining the melting points of benzophenone (m.p. = 47-50 °C), pimelic acid (m.p. = 105-105 °C), and benzoin (135-137 °C) 2. Determine the melting behavior of an “unknown” material supplied by your instructor 3. Determine the identity of your “unknown” by doing a mixed melting point Chapter 5 – Parts B and C 4. For experiment B use a mixture of 10 mL 95% ethanol and 10 mL of water 5. For experiment C use a mixture of 25 mL 95% ethanol and 25 mL water. Use glass beads to pack the fractionating column. Postlab questions: 1-4, p. 22 and 3, 5, p. 58.
Jan 28- Feb 3	Prelaboratory preparation: Read Chapter 3, Recrystallization. Answer in your laboratory notebook Prelaboratory questions 1-5, p. 32. Experiment: Perform part B as written. Note Carefully: Retain the products of all experiments until you are given instructions about what to do with them. In this case, retain the recrystallized solid for determination of its melting point after it is completely dry (one week). Additional note: In an experimental procedure, the specification of a quantity as, for example, “60 mg of benzoic acid” does not mean precisely 60 mg, but rather about 60 mg weighed to the precision of the balance. To insure reproducibility in weighing, always use the same balance when you tare the container and later when you weigh the container plus the recrystallized material. Postlab questions: 1- 5, p. 32.
Feb 4-10	Prelab preparation: Read p. 59 (first paragraph only), pp. 67-68 (through Table 7.1) and Chapter 8, Thin Layer Chromatography. Prelab questions: 1-5, p. 78. The aim of this experiment is to teach the principles and techniques of thin layer chromatography (TLC) in order for you to become facile in using it as an analytical technique for estimating the purity and identity of products. Your chromatograms, together with your observations, will constitute your report for this experiment. They will be judged on the basis of appropriate concentration of material applied to the slide, correct development of the slide, care in marking developed spots, and correct calculation of Rf values. You will use solutions of dyes to gain experience with the experimental techniques. 1) Choose any one of these dyes, and after application to the slide, attempt development with a solvent of low polarity, such as hexane, cyclohexane, or ligroine. Record your observations. 2) Redevelop the same slide with a solvent of higher polarity like ethyl acetate, or ethanol, or with an aromatic solvent such as toluene which has a greater ability to dissolve other aromatic substances, such as these dyes. Record your observations. 3) Try using mixtures of these solvents, using fresh slides as necessary, recording your results each time, until you have succeeded in finding one or more solvents or solvent mixtures in which the dye migrates with an Rf between 0.3 and 0.6. 4) Use the solvent or solvent mixture you have selected to attempt to separate a mixture of dyes. Your TA will give you additional instructions. Postlab questions: 1-4, p.78.
Feb 11-17	Read Chapter 4, Extraction. Prelab questions: 1-5, p. 45-46. Experiment: Part B – The unknown contains an acidic and neutral component only. After performing the instructions of the first sentence of the procedure section, skip to the third paragraph which begins, “ To isolate the acidic component…..” Note Carefully: In this and all subsequent experiments, ether solutions are to be concentrated by distillation, not by evaporation into the atmosphere. The distilling receiver is connected to the condenser with the vacuum adapter and is cooled in an ice bath. A piece of rubber tubing is led from the tubulation of the adapter into the sink trough, so that vapors which escape the apparatus are removed in the water stream. Do not distil to dryness! Use the “house” vacuum line to remove the last traces of ether. Also note: In the event that the acidic component does not precipitate on acidification with HCl, extract the acidic component with ether and distill the ether to obtain the component. Each component separated will be characterized by melting point and TLC in the following manner: 1) Using the same experimental approach that you used in the TLC experiment, find a solvent or solvent mixture that effectively separates on TLC the possible components of the mixture which you separated by extraction. Since the materials are colorless to the eye, they must be visualized by use of UV lamps. Mark the spots under the UV light for further analysis. Note that because they have greatly different polarities, the acidic materials migrate at greatly different rates from those of the neutral materials in any one solvent. Hence, two solvent systems must be found: one for the acidic components, one for the neutral components. 2) Use the appropriate solvent system to compare the Rf value of the acidic component of your mixture with those of standards of known structure. Apply both known and standards in separate spots to the same slide, label for correct identification, develop, and mark the spots. Identify your unknown by seeing which reference material its Rf matches. Repeat for the neutral component. Postlab questions: 1-7, p. 45.
Feb 18-24	Read Chapter 10: Steam Distillation of Essential Oils. Prelab questions: 1-5, p. 92. Experiments: Part A., p. 88 and Part D., pp. 90-91. Note the following change: Ether, not methylene chloride, will be used to extract the clove oil. The ether is removed by distillation as described earlier.
Feb 25- Mar 10	Finish steam distillation. Post lab questions: none Read Chapter 16: Properties of Hydrocarbons. Prelab questions: 1-5, p. 185. Experiments: Parts A – F, p. 184. Postlab questions: 1-4, p. 184, and 6, p. 185.
Mar 3-8	SPRING BREAK
Mar 11-17	MIDTERM EXAM Read Chapter 17: Nucleophilic Substitution of Alkyl Halides. (Related material: Wade, Chapter 6.) Prelab questions: 1-4, p. 192. Experiments: Parts A – C, pp. 188 – 191. Postlab questions: 1 – 5, p. 192. Note: The answer to question 3 should be based on your own data and stated in terms of the polarity of the solvent mixtures you used.
Mar. 18-24	Read Chapter 20: Dehydration of Alcohols (Related lecture text material: Wade, pp. 317 – 318.) Prelab questions: 1 – 5, pp. 208-209. Experiment: Part A, pp. 206 – 207. Note: The experiment is performed exactly as described using the fractionating column packed with glass beads. If the product appears cloudy upon final distillation, it is because it has traces of water condensed in it. You can ensure that your product is free of water by drying the crude product as described and by drying the glassware used in the final distillation before use. Using the air heater to dry the glass surfaces is an approved technique. Test your product, as well as an acetone blank, and cyclohexanol as described in test D on p. 184. Postlab questions: 1 – 6, p. 208.
Mar 25-31	Handout: Oxidation of Cyclohexene. (Related lecture text material: Wade, pp. 364 – 366.) Prelab and postlab questions are in the handout. IMPORTANT NOTE: Wash all glassware needed for next week’s experiment before you leave the lab. Do not wait until next week!
Apr. 1-7	Read Chapter 19: The Grignard Reaction. (Related lecture text material: Wade, pp. 432 – 440.) Prelab questions: 1 – 5, p. 204. Experiments: Parts A and B (macroscale), pp. 198 – 201. Note: The key to success in this reaction is a dry environment! Carefully dry all glassware as described by the TA. Immediately replace the caps on all reagents used, especially the ether. Note the following procedure change: Part B – After the ether layer is dried over magnesium sulfate, transfer the ether to a tared round bottom flask and simple distil to remove the ether. Do not distil to dryness. Remove the last traces of ether with the “house” vacuum. Record the weight of the crude product and save a small sample for TLC analysis. Triturate the solid product remaining in the flask with cold petroleum ether to remove the biphenyl side product. Carefully decant the petroleum ether/biphenyl solution and save it for analysis by TLC. Recrystallize the remaining solid from isopropyl alcohol. Measure and record the weight and melting point of the purified triphenylmethanol. Calculate the % yield. Analyze the crude product, the petroleum ether extract, and the recrystallized product by TLC using petroleum ether as the solvent.
Apr. 8-14	Finish Grignard Reaction. Postlab question: 1 – 4, p. 204. Read Chapter 18: Properties of Alcohols. (Related lecture text material: Wade, pp. 459 – 461, 470 – 471, 484 – 485. Prelab questions: 1 – 5, p. 196. Experiments: Parts C – E, pp. 195 – 195. Postlab questions: 2 – 6, pp. 195 – 196. Important Note: Wash all glassware and make sure that all of the necessary equipment is in your drawer for check-out next week. It is your responsibility to replace anything broken during the semester.
Apr. 21-26	Final Exam (cumalative) and check out.