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Organic Chemistry Lab CHM 266 Spring Semester, 2007 Science Building 451 8:00 - 11:00 A.M. MW Instructor: Dr. Tahmassebi Office: Science Building 484 Phone: 481- 6297 Email: tahmassd@ipfw.edu Text: Introduction to Organic Laboratory Techniques a small scale approach, 2nd Edition , by D. L. Pavia, G. M. Kriz, G. S. Lampman, and R. G. Engel, Saunders College Publishing, 2005 Lab Separates The Synthesis of A Superabsorbent Polymer , Charles M. Garner, Chemical Education Resources, 2000 Tentative Schedule of Experiments Changes may occur but you will be given sufficient notice. Experiment Title Reference 1 Oxidation of Cysteine to Cystine (Synthesis, 20 pt.) Handout, Technique 25. pp. 878- 2 Multistep Synthesis (Synthesis, 40 pt.) Part 1 Coenzyme Synthesis of Benzoin Pavia, Exp. 34A, pp. 288- 294, Review GC-MS notes Experiment Title Reference
Part 2 Benzil Pavia, Exp. 34B, pp. 294- 296, Technique 25.6, pp. 882- Part 3 Tetraphenylcyclopentadienone Pavia, Exp. 35, pp. 300- 302 3 Synthesis and Recrystallization of Adipic Acid (Synthesis 20 pt.) Handout 4 Free Radical Chlorination (Analytical, 20 pt.) Handout, Review Technique 22, pp. 837 – 857 5 The Synthesis of a Superabsorbent Polymer (Synthesis 20 pt.) Lab Separate 6 Friedel Crafts Acylation (Synthesis 20 pt.) Pavia, Exp. 59, pp. 530- 537, Technique 16.1,2,8, pp. 764-772, 778- 7 Triphenylmethanol (Synthesis 20 pt.) Pavia, Exp. 36, pp. 303- 311 8 Mutarotation of Glucose (Analytical 40 pt.) Handout, Review Technique 23, pp. 857 - 866 9 Nitration of methyl benzoate (Synthesis 20 pt.) Pavia, Exp. 43, pp 352- 10 Esterification, Design of Procedure (Synthesis, 40 pt.) Handout 11 Carbohydrate Reactions (Analytical, 20 pt.) Pavia, Exp. 52 pp. 443- 12 Identification of an Organic Unknown (Analytical, 40 pt.) Handout
Grading
12 Reports 320 points Notebook 130 points Technique 50 points Quizzes 100 points Lab Exam, Friday May 4, 8-10 A.M. 100 points Total 700 points Cutoffs A > 90% (630) B > 80% (560) C > 70% (490)
Lab reports are due the first 15 minutes of lab on the announced date. After that the report is considered late. You can not complete your report in lab. Technique You will be graded on your safety practices and the skill with which you perform experiments. This technique grade will be assigned at the end of the semester. Normally, I will take the total grade of your reports, divide that by the total possible report grade and multiply by 50. Your technique grade would then reflect how well you performed the lab and knew the material. However, I reserve the right to deduct points from this value if the following reasons. Safety practices as described in the safety sheets, notes, and lab manual are not followed. This particularly includes not wearing goggles. Suggestions by the instructor for experimental procedure or apparatus set-up are not followed. Student samples stored in the refrigerator or drawer are not properly labeled. The caps of reagent bottles have not been replaced after use. Reagents and solvents have been contaminated. This can be avoided by not replacing unused reagent or solvent to their original containers. Place unused material in the waste bottles. Also, you should not directly pipet reagents and solvents from bottles. Pipets that have not been cleaned and dried have been a cause of contamination previously. Pour liquids into a beaker or flask and then use the pipet. If your pipet is dirty, it affects only your experiment and not others. This requires that you minimize how much material is poured out so that we don’t waste expensive chemicals and don’t unnecessarily add to the waste that must be disposed. Magnetic stirrers, hotplates, water faucets, gas lines, m.p. and air lines have not been shut off. Hood sashes have not been closed. The m.p. apparatus and balances should be turned off at the end of the lab period if you are the last to use them. Reagents and equipment are not properly replaced to their shelf or drawer location. A student has a higher than usual rate of equipment breakage. The instruments have not been treated with care. If water is to be used for your experiment other than a hot or cold water bath, always use the deionized water from the gray faucets. After cleaning glassware and equipment with tap water, always rinse with deionized water. There are sufficient contaminants in tap water used for lab to adversely affect experiments. I have chosen experiments that generally work well despite whatever mistakes are made, but it is always good technique to use deionized water.
The number of points deducted will be determined by the instructor and announced to the student. This policy is not meant to be punitive but to help you become competent in lab. Although you will see some of these techniques in later lab courses, CHM 265 and CHM 266 are essentially designed to be the only courses where you will learn to function in a lab that does organic chemistry. When you get to a job, you may be expected to perform recrystallizations and distillations. If you don’t learn it here, you won’t impress your coworkers and bosses by learning it on the job later. Notebook You will be required to keep a laboratory notebook using the following guidelines.
- A bound notebook must be used.
- A table of contents must be placed at the beginning of the notebook. Number the pages of the notebook if necessary.
- Use only pen in recording entries.
- When making corrections, place a single line through the error. e.g. Then 10 ml 8 ml of ethanol was ...
- Mark the date of each new notebook entry.
- Two types of experiments will be performed throughout the course. Either you will synthesize and isolate a compound (synthesis experiment) or you will perform a specific laboratory technique or analytical test. (analytical/technique experiments). The notebook entries for each type of experiment will be somewhat different. For analytical/technique experiments use the following format: Analytical/Technique Notebook Entries a. Place the title of the experiment at the top of the page. b. Write the reference for the procedure. (See last two pages for preferred style.) c. Write out a table containing the names of the compounds used, pertinent known analytical data such as m.p., b.p. etc. (obtained from the CRC Handbook of Chemistry and Physics, Merck Index, or Chemfinder) and any particular hazards presented by the compound. Under hazards, indicate whether the compound is known to be toxic, flammable, explosive, an irritant, etc. (obtained from the Sigma Aldrich Library of Chemical Safety, the Merck Index, or Chemfinder). This information may appear on the bottle's label. d. Write the procedure you used to perform the experiment in full English sentences. Avoid the use of the pronouns I, we, and they. Place the date on which that portion of the procedure was performed on the left-hand side at the beginning of the narrative. Be concise, but include enough information so that anyone can read your notebook and do the experiment. e. Place all data collected (masses, m.p., b.p.) in a separate data section. Do not mix data with the narrative. Also clearly indicate your final results. Write the date on which the observations were made on the left-hand side at the first entry for that day. (See the example given.)
You will receive an F for the course. You should realize that each instrument’s output consists of a certain amount of irreproducible electronic noise. The probability that the same instrument will give the same exact results twice is negligible. On time attendance is expected at all of the lab sessions. One point will be deducted for tardiness of 15 minutes from your techniques grade. If you are more than half an hour late, you are not allowed to come in to the lab. All cell phones must be turned off in the lab. If your phone rings during lab session, one point will be deducted from your techniques grade. Although not required (yet), some schools and instructors require outlines of procedures to insure that experimental procedures have been read. If it appears that some students are not coming prepared to lab, it may become a requirement. Procedure changes and announcements for the course will be given in lab and on the CHM 266 Home Page. Lectures explaining the experiments, practical considerations in organic chemistry, and some theory will be given on many but not all lab periods. The notes will be presented on transparencies. You have been provided with the notes for the first two lab lectures. The remaining lectures for the semester must be printed from the internet. See the CHM 266 Home Page. Use the computers on campus for your printing needs. It is your responsibility to have these materials ready prior to lab. You can use the computer in Organic lab to look up compound properties on www.chemfinder.com and other necessary information but may not print. It is required to save your data on a zip disk (preferably 100 MB) and bring it to lab. You will be assigned a drawer and a hood for the semester. The locker will be only yours, but the hood will be shared with other laboratory sections. You will be expected to clean your hood at the end of each lab period. Your drawer will be expected to be clean at the end of the semester. Clean it on a regular basis so that it does not become stained. The stockroom personnel are very busy, please do not make extra work for them. Return all chemicals and equipment back to their proper locations. Clean up after yourselves. In several ways, organic chemistry lab is much different than general chemistry lab. In certain ways, organic chemistry lab reflects what it's actually like to work in a lab more than general chemistry. Most experiments will last more than one lab period. Often, you will be working on more than one experiment at once. If you make a mistake and the experiment doesn't work, it will have to be repeated until it does work.
The experiments involve techniques used by people who do organic chemistry part or all of the time: distillation, recrystallization, reflux, IR, NMR etc. I can't or won't necessarily stay late or show up early to accommodate your schedule. If you don't get the experiment done by the due date because you did not spend all the time in lab you could for it, then that's your problem. I realize that some students have difficult schedules. For that reason, I am trying to be as flexible as possible. In the end however, you must complete the same amount of work as everyone else. Occasionally you may have to wait for a particular reaction to finish, or you may complete a procedure early. This is a good time to work on your notebook, reports, or other experiments. It is not necessary but may be helpful to write an outline of the experiment before you do it. People often find that it takes less time to do the experiment and fewer mistakes are made. I often do this myself. To reflect more stringent safety requirements imposed by various governmental agencies, you will be required to label all samples that are to be stored in your drawer or refrigerator. Using one of the labels with the 4-color hazard diamond, write down the name of the compound, the date, and your initials. Then when available, write the hazard numbers in the appropriate boxes. Further explanation will be provided in lecture. Please always place your thermometers with the bulb pointing downwards in the plastic tubes mounted on the inside of your lockers. You will be expected to know the following from general chemistry lab. These topics will not be covered in lab lecture this semester. Either read the appropriate section in your lab manual if you have forgotten or ask me questions. How to calculate molecular weights How to calculate limiting reagents How to calculate theoretical yields How to calculate % yields How to use a balance and measure masses How to use graduated cylinders, volumetric flasks, and volumetric pipets How to use Bunsen burners Useful References
- R. C. Weast, ed. "CRC Handbook of Chemistry and Physics", 70th ed. CRC Press, Boca Raton, 1989, revised annually.
- S. Budavari, ed. "The Merck Index", 12th Ed. Rahway, NJ.: Merck & Co., 1996
- J. Nagarkatti, C. Lane, "Aldrich Catalog and Handbook of Fine Chemicals", Aldrich Chemical Co. Milwaukee, 1992.
- R. E. Lenga, ed. "The Sigma-Aldrich Library of Chemical Safety Data Edition I", Aldrich Chemical Co. Milwaukee, 1998.
