COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 CHEM C2507, SPRING 1999 Intensive General Chemistry Laboratory STUDENT MANUAL FOR CASE STUDY Alan Szeto and Luis Avila TABLE OF CONTENT PAGE I. SCHEDULE AND DUE DATES …………………………… 2 II. INTRODUCTION …………………………… 3 …………………………………………… 4 COLLABORATIVE LEARNING TEAM ROLES CHEMICAL ANALYSIS III. …………………………………… 4 PLANNING AND WORKING IN THE LABORATORY LABORATORY SAFETY ………………………..……..…… PLANNING BEFORE A LAB PERIOD 6 …………………… 7 CLASSICAL ANALYSIS PROCEDURES …………………… 8 INSTRUMENTATION ANALYSIS PROCEDURES …… 9 …………………………… 9 ADVANCED PROCEDURES SUGGESTED GUIDELINES FOR ANALYSIS PROGRESS REPORTS SUPPORT …………… 9 …………………………………… 10 …………………………………………………… 10 IV. EVALUATION …………………………………………… V. CASE STUDY PROJECTS 12 CASE I: SUSPICIOUS WASTE DISPOSAL …………… 13 CASE II: ENVIRONMENTAL POLLUTION …………… 13 CASE III: HAZARDOUS CHEMICALS IDENTIFICATION 14 VI. BIBLIOGRAPHY 15 VII. SUPPORT INFORMATION …………………………………………… …………………………… 16 FINAL VERSION Page 1 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 SCHEDULE AND DUE DATES APRIL 5/6 Lecture Introduction to Collaborative Learning (CL) Introduction to Case Study Introduction to Chemical Analysis Chemical Analysis Quiz Self-assessment (Pre-Case Study) Laboratory Students self-assemble into groups of 3 to 4 Members of each group sign up on the Role sheet Each group selects a case Each group obtains sample(s) Phase I Analysis Each group submits Phase I Progress Report Seminar Topic: Chemical Instrumentation 12/13 Monday/Tuesday Laboratory Phase II Analysis Each group submits Phase II Progress Report (if ready) 16 Seminar Topic: Chemical Literature 19/20 Monday/Tuesday Laboratory Phase II/III Analysis Each group submits Phase II/III Progress Report (if ready) 23 Seminar Topic: To be announced 26/27 Monday/Tuesday Laboratory Open 30 Friday Lecture Self-assessment (Post-Case Study) Course Evaluation Friday Due Date Case Study Group Report 9 Monday/Tuesday Friday Friday Friday MAY 7 VENUES Lecture/Seminar Laboratory 209 Havemeyer Hall 302 Havemeyer Hall Page 2 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 INTRODUCTION Welcome to Case Study! The last segment of the Intensive General Chemistry Laboratory (CHEM C2507) course will be a Collaborative Learning (CL) exercise. This exercise will involve the performance of a variety of Case Studies by groups of three to four students. You will be evaluated based on your contribution as an individual and on the overall success of your group. COLLABORATIVE LEARNING According to Felder and Brent (1994):1 Collaborative Learning (CL) is instruction that involves students working in teams to accomplish a common goal, under conditions that include the following elements: 1. Positive interdependence. Team members are obliged to rely on one another to achieve the goal. If any team member fails to do their part, everyone suffers consequences. 2. Individual accountability. All students in a group are held accountable for doing their share of the work and for mastery of all of the materials to be learned. 3. Face-to-face promotive interaction. Although some of the group work may be parceled out and done individually, some must be done collectively, with group members providing one another with feedback, challenging one another’s conclusions and reasoning, and perhaps most importantly, teaching and encouraging one another. 4. Appropriate use of collaborative skills. Students are encouraged and assisted to develop and practice trust-building, leadership, decision-making, communication, and conflict management skills. 5. Group processing. Team members set group goals, periodically assess what they are doing well as a team, and identify changes they will make to function more effectively in the future. Understanding elements 1 to 5 above is crucial for the success of your team in the CL exercise. 1 Felder, R. and R. Brent. ERIC Document Reproduction Service Report ED 377038 (1994). Page 3 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 TEAM ROLES2 In each team, each member should select one of the following roles: • • • • The coordinator, organizes the Case Study into subtasks, allocates responsibilities, and keeps the group on task. The checker, monitors both the solutions and every team member's comprehension of them. The recorder, checks for consensus and writes the final group solution. The skeptic, plays devil’s advocate, suggests alternative possibilities, and keeps the group from leaping to premature conclusions. You will have the freedom to negotiate and select your own role. Make sure you sign up on the Role sheet kept by your instructor. The group as a whole will come to a consensus in choosing one specific Case Study among the available cases. CHEMICAL ANALYSIS The purpose of Chemical Analysis is to establish the composition of naturally occurring or artificially manufactured substances. The individual components in these substances are called analytes. Traditionally, Chemical Analysis is done in two distinct steps. First, qualitative analysis is used to identify the sample components. This is followed with quantitative analysis, by which the relative amounts of these components are determined. In this Case Study, you will perform mainly qualitative analysis of organic and/or inorganic unknowns. Chemical Analysis has remained a prominent field throughout the history of Analytical Chemistry for an obvious reason: we are curious to find out the composition of different materials. During the last few decades, especially, not many branches of any science have undergone so much change in the equipment and procedures used as has the field of Chemical Analysis. This revolution has significant impact on how the principles of chemistry are taught today. The revolution in analysis also has had wide influence on technology in general because of the far greater accuracy with which chemical determinations can be made. While the impact of vastly improved Chemical Analysis has been felt by essentially all branches of science, dramatically more precise data have been of notable significance in the areas of pollutants and pharmaceuticals. Classically (essentially prior to the 1940s), the subject of Chemical Analysis was divided into two readily understood areas. Qualitative analysis concerned simply with the identification of the components in a mixture (or the constituents of a compound), sometimes accompanied by observations (rough estimates) of whether certain ingredients may be present in major or trace proportions. Quantitative analysis concerned with the amounts (to varying degrees of precision) of all or frequently of only some specific ingredients of a mixture or compound. Quantitative analysis involves gravimetric analysis (where changes in the weight of samples or precipitates 2 Johnson, D. W., R. T. Johnson, and K. A. Smith. Cooperative Learning: Increasing College Faculty Instructional Productivity. ASHE-ERIC Higher Education Report No. 4. George Washington University, 1991. Page 4 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 are the underlying basis of calculation) and volumetric (titrimetric) analysis (where solutions of known concentration are reacted in some fashion with the sample to determine the concentration of the unknown). With the massive use of chemical instrumentation today (such as Infrared Spectroscopy and Nuclear Magnetic Resonance), Chemical Analysis is convenient and reliable. A chemist (or analyst) who has a sample in hand, and needs to know what it is, cannot possibly be aware of all the reported data for comparison with the properties of the unknown. Thus, a systematic approach is essential. This approach must first exclude as many structural possibilities as possible; then, reduce the number of possible structures to just a very few (say, three or four) possibilities; and finally, establish and confirm one structure. The approach you will use in this Case Study will be somewhat similar. You will first determine whether you have a mixture of components in your unknown sample. Once you have isolated the pure components, collect data on as many of the physical properties of a component as possible. With the help of instrumentation, you will establish a short list of possible identities of your component. Finally, you will confirm the exact identity by performing confirmation testing. Unfortunately, in Chemical Analysis we are often confronted with either of the following extreme situations:3 1. Determination of the identity of a compound that has no prior history. This is often the case for a natural products chemist who must study a very small amount of sample isolated from a plant or an animal. A similar situation applies to the forensic chemist who analyzes very small samples related to a lawsuit or crime. 2. The industrial chemist or college laboratory chemist who must analyze a sample that contains a major expected product and minor products, all of which could be expected from a given set of reagents and conditions. It is entirely possible that such a sample with a welldocumented history will allow one to have a properly preconceived notion as to how the analysis should be conducted. The background of each case that is available in this Case Study should provide important clues as to what the unknown could be, even before you begin the analysis. Adequate planning and research prior to carrying out a lab procedure will assure you positive progress (in a timely manner) toward identifying the unknown. On the other hand, team-work, frequent communications, frequent reflection on the obtained data, patience, and positive attitude are also imperative if you are to have an enjoyable experience in the laboratory. Often, you will be confronted with limitations in availability of time, space, resources, equipment, and other unforeseeable constraints. Therefore, sensible decision-making skills must be exercised. Do not be afraid to experiment at the beginning of the analysis. Decision-making skills will improve with increasing experience. 3 Shriner, R. L., et al. The Systematic Identification of Organic Compounds, A Laboratory Manual. 6th ed. John Wiley & Sons: New York, 1980. Page 5 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 PLANNING AND WORKING IN THE LABORATORY The following guidelines will facilitate your work during the four-week period. LABORATORY SAFETY Basic Safety All laboratory safety protocols in CHEM C2507 will be strictly enforced (refer to pp. 3 – 6 of the Intensive General Chemistry Laboratory Manual, Spring 1999, or obtain a Safety Check-list from Alan Szeto). Violation of any safety protocol may result in points deduction on the Written Evaluation by Instructor and/or dismissal from the laboratory. Safety has two aspects: prevention of accident and response to emergency. The golden rule of thumb is to use your common sense at all time. Always be aware of your surrounding. Treat your classmates and chemicals in the laboratory with respect. Do not work in the laboratory alone or perform any unauthorized experiments. Ask your instructor whenever you do not know how to perform a procedure. Notify your instructor immediately when there is an accident (including broken glassware, major chemical spill, and bodily injury). Material Safety Data Sheet (MSDS) http://www.chem.ucla.edu/Safety/ Federal law requires that manufacturers and distributors of chemicals provide users with Material Safety Data Sheets (MSDS). MSDS is a fairly concise technical document that gives information on any particular chemical among the over 10,000 frequently encountered chemicals in research laboratories and industries. The information includes contact address and phone number of the chemical supplier, chemical names, physical and chemical properties, physical hazards (such as flammability, reactivity, explosibility, etc.), toxicity data and health hazards, storage and handling procedures, emergency and first-aid procedures, and disposal and transportation information. Today, the MSDS for a chemical can be conveniently located by submitting the name of the chemical to a MSDS searchable database on the internet. Many of such databases exist, and they can be found using the world-wide-web address provided. In the Case Study, you will come into contact with many chemicals that you may be unfamiliar with. It is your responsibility to read the MSDS for a chemical that you plan to use for your particular experiment or analysis. This task is similar to reading the safety warning of an experiment in the Intensive General Chemistry Laboratory Manual, Spring 1999, before you actually perform the experiment. Chemical Waste Disposal No chemicals can go down the sink, period. Aqueous, organic, and solid wastes should be disposed properly in clearly labeled containers. Follow the instructions on the Intensive General Chemistry Laboratory Manual, Spring 1999, page 6. Ask your instructor when in doubt. Page 6 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 Chemicals Storage Toward the end of a lab period, you will be asked to clean-up your working area in the laboratory. At that time, decide what samples of chemicals you will save for the next lab period. In general, glass vials of various sizes work well in storing aqueous and organic solutions and solid samples. Use parafilms wherever appropriate. If you are not certain how to store properly your particular sample, ask your instructor. Most samples and chemicals will be shelved in a metal solvent cabinet located in 302C Havemeyer Hall. PLANNING BEFORE A LAB PERIOD There is no formal “Pre-lab” write-up required. However, without preparation in advance, you will quickly find yourself wasting time and chemicals in the laboratory. • The first task in any research endeavor consists of searching the literature. Read the background of the case thoroughly. Use the Chemistry Library to look up references. • Using the scientific method, analyze the problem, make a hypothesis, and design experiments to collect data. • Use your laboratory notebook to take notes and make observations. Keep all information in an organized manner. You will never know what pieces of information will become the key to your success. • Although you will be given a slightly large quantity of unknown sample, always remember to save samples at various stages of your analysis. Exercise your common sense to decide how much of a sample you will use for a particular procedure. • Review your chemistry concepts and apply them effectively in the laboratory. • Each member of the group may conduct and analyze experiments independent of each other. Toward the end of a lab period, the members of the group will meet, share their findings, and prepare for the next lab session. • If you want to perform an experiment that is not listed on the next page in the Classical, Instrumentation, and Advanced Analysis procedures, ask your instructor for permission. Your instructor will contact either Alan Szeto or Luis Avila for proper approval. Page 7 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 CLASSICAL ANALYSIS PROCEDURES Thin-layer Chromatography (TLC) Refer to IGChem Lab Manual, pp. 109 – 127 Melting Point (m.p.) Analysis Refer to Mayo, pp. 41 – 44 Boiling Point (b.p.) Analysis Refer to Pavia, pp. 551 – 554 Simple Distillation Refer to Pavia, pp. 554 – 558 Solubility Tests Refer to Shriner, pp. 90 – 109 Solubility Studies in Organic Solvents Refer to Shriner, pp. 109 – 112 Classification Tests Refer to Shriner, pp. 16 – 17 Titratable Acids If you are certain that you have a pure component (solid or aqueous) that is acidic, titrate to obtain the end point and pKa of the acid. Refractive Index Determination Refer to Mayo, pp. 39 – 40 Filtration Refer to Mayo, p. 105 Crystallization Refer to Mayo, pp. 103 – 105 Simple Density Determination If you are certain that you have a pure liquid, determine its density using an analytical balance and a 10-mL graduated cylinder. Column Chromatography Refer to IGChem Lab Manual, pp. 109 – 127 Liquid Extraction Refer to Fieser, pp. 56 – Page 8 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 INSTRUMENTATION ANALYSIS PROCEDURES Gas Chromatography (GC) Refer to IGChem Lab Manual, pp. 109 – 127 Fourier-Transform Infrared Spectroscopy (FT-IR) Refer to IGChem Lab Manual, pp. 52 – 56; Avila, pp. 8 – 12; IR Tutor 1.1 Nuclear Magnetic Resonance (NMR) Refer to Mayo, pp. 493 – 499 and 469 – 474 High Performance Liquid Chromatography (HPLC) Refer to IGChem Lab Manual, pp. 109 – 127 Visible Spectrophotometry Refer to IGChem Lab Manual, pp. 21 – 34 ADVANCED PROCEDURES Preparation of Derivatives Refer to Shriner, pp. 18 – 20 SUGGESTED GUIDELINES FOR ANALYSIS Phase I – Physical Descriptions, Physical Properties, and Phase Separation • Visual Examination Write down the color, odor, number of phases, and physical characteristics of the sample(s) received. • Physical Properties Determination If your sample is a solid, determine its melting point (m.p.). Test the solubility of the solid in several solvents. Take notice of the polarity of the solvents. Determine the density if you know you have a pure liquid. Determine the refractive index. Examine the purity of your sample and its components with m.p. and TLC. • Separation of Components in a Mixture Filter the sample if necessary. Keep both the solid and the filtrate. If the filtrate shows immiscible phases, perform a liquid extraction. Hint: Do not discard any of the separated phases since you do not know the solubility of the compound or mixture of compounds you are to determine. Page 9 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 Phase II – Chemical Analysis • Solid sample: - Prepare a solution of the solid and perform a TLC. - Separate the components using column chromatography. - Take an IR spectrum of the separated fractions using DRIFT or KBr pellet. • Aqueous phase: - If your aqueous solution is acidic, do a potentiometric titration to determine the number of replaceable hydrogen atoms in the molecule. From the titration curve, determine the pKa . - Do an HPLC of the aqueous phase and compare it with standards. • Liquid organic mixture: - Perform a TLC. - Perform a GC of the solution. - Take a capillary film IR spectrum of the separated fractions using salt plates or 3M cards. Phase III – Further Chemical Analysis and Positive Identification Testing Once you have characterized the unknown(s) via melting point, acid-base titration, chromatography and visible and IR spectroscopy, you will receive a series of known compounds and their NMR spectra. You should look up the physical and chemical properties of these compounds in the CRC Handbook of Chemistry and Physics and correlate them with the information you have gathered during your data collection. PROGRESS REPORTS Each group is required to submit three Progress Reports. Although they do not have definite due dates, it is strongly recommended that the group should get together after a specific phase of the Case Study is completed to discuss the group progress among the members themselves and with the instructor. Fill out the Progress Reports completely (referring to the sample available in the laboratory) and obtain the signatures of each group member as well as the instructor. Turn in a Progress Report as soon as it is ready (referring to the Schedule and Due Dates section). SUPPORT Instructors • • The laboratory instructors will supervise the activities during the data collection process and will help you to make decisions about procedures, techniques, and data interpretation. The instructors will hold office hours outside the laboratory to help you to solve problems. Refer to the Support sheet for more information. Page 10 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 Chempreps (304 Havemeyer Hall) Chempreps has an inventory of glasswares, chemicals, and accessories. Staff in Chempreps will assist you with your needs, for example, if you cannot find a certain item in the laboratory. You are strongly advised to ask your instructor before walking over to the Chempreps window. Your instructor will clarify the exact item you need, tell you whether the item you need is in the laboratory, and if the item is not in the laboratory, advise you whether it is necessary and worthy to get it from Chempreps. This simple communication will assist the staff in Chempreps to help you and prevent a lot of unnecessary access of the inventory in Chempreps. Chemistry Library (4th floor Chandler Hall) The Chemistry Library has a remarkably large collection of chemical literature from textbooks, manuals, journal titles, to reference sets. There are computer terminals available for you to search conveniently for chemical literature electronically. The Reserve section of the library contains all the primary references used to prepare this Manual; these references are available to you on a two-hour loan basis. For further assistance in using the Chemistry Library, consult the librarian. MacLab (310 Havemeyer Hall) MacLab has a number of Macintosh computers all connected to a common server. To use a computer there, type in “gchem” as the login name and then press enter (no password is necessary). You can use valuable computer software there such as IR Tutor 1.1 or access the internet through Netscape to obtain information from countless numbers of sources. Other applications such as Words and Excel are also available. However, to access these later applications, you need to obtain special login name and password from your instructor. Off-hours Use of Laboratory Due to safety and security reasons, you are allowed to use the laboratory (302 Havemeyer Hall) only during the dates listed under the Schedule and Due Dates section. However, if you need to repeat a measurement during any morning (Monday through Friday) when there is no class, you may ask permission from Alan Szeto via e-mail by 9:00 p.m. the night before. Page 11 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 EVALUATION Your grade for the Case Study will be assigned using the following criteria: Chemical Analysis Quiz Individual 50 points Phase I Progress Report Group 30 points Phase II Progress Report Group 45 points Phase III Progress Report Group 45 points Written Evaluation by Instructor Individual 25 points Completion of Self-assessments Individual Case Study Final Report Group Total 5 points* 200 points 400 points *Graded on credit/no credit basis. Chemical Analysis Quiz – This 30 minutes, open-book quiz aims to evaluate your grasp of the bread and butter of Chemical Analysis and your understanding of the theory and operation of classical and instrumentation procedures. Your satisfactory performance on the quiz is your license to participate in this Case Study. You may be asked to perform some lab procedures in front of your instructor to prove that you are competent enough to work in the laboratory if you fail the quiz. Progress Reports – These reports are to document data and communications among group members and your instructor. It is an important summary of discoveries and its preparation and organization will show the workmanship of the group. It must be turned in to the instructor in a timely manner. See the Progress Report section for more information. Written Evaluation by Instructor – This evaluation provides your instructor a medium to evaluate your lab performance as an individual. Your contribution to the team observed by your instructor will also be evaluated objectively. Self-assessments – This five points will be awarded to you after you complete both the Pre- and Post-Case Study Self-assessments. These assessments contain questions that require your sincere response so that chemical education in the future can be improved. Case Study Final Report – At the end of the Case Study each group will present a joint written report about the activities and the conclusions reached. Only the names of the individuals who actually participated should appear on the final product with their team roles identified. This report will be about eight to ten pages long (excluding graphs and spectra) in a journal article style. This report should resemble high quality work and critical thinking and accurate Page 12 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 description of scientific concepts required of a professional. This report will be held to the highest standard in grading. CASE STUDY PROJECTS CASE I THEME: SUSPICIOUS WASTE DISPOSAL Description: The Department of Sanitation is conducting a joint investigation with the NYC Police Department to determine the chemical identity of a pungent liquid found in a series of five metallic containers in a public Dumpster in Uptown West Manhattan. The waste management workers reported to the Engine 234 – NYC Fire Department that one of their colleagues suffocated after handling one of the containers. The paramedics took the injured worker to St. Luke’s Hospital and reported the case to the NYC Police Department. The forensics laboratory sent a sample of the liquid to Columbia chemists to crossreference their findings about the chemical identity of the unknown liquid. This improper disposal could result from the operation of legal stores in the zone (an Auto Mechanic shop or a pickle production store) or from the operation of a clandestine laboratory suspected to be processing alkaloids in the area. Your goal: Identify the unknown liquid waste using Chemical Analysis and suggest the disposal source. CASE II THEME: ENVIRONMENTAL POLLUTION Description: An investigation was conducted to determine the cause of the death of approximately 240 bottlenose dolphins, Tursiops truncatus, along the Texas coastal ecosystem during 1992. The possible causes of death include industrial pollution, agricultural runoff, fishery interaction, biotoxins, and/or disease.4 The investigation of all potential causative factors have been explored using laboratory analyses for determination of water quality and detection of priority pollutants and pesticides in the water, examination of local fisheries and interviews with fishermen, analysis of water and shellfish samples for biotoxins. Gross necropsy and histiopathology from the animal carcasses were also performed and the forensics laboratory has sent a sample of frozen liver, kidney, and stomach tissues for Columbia chemists to investigate the nature of the chemicals metabolized by the animals. Investigation results indicate that two 4 Ann Colbert. Forensics Program, National Marine Fisheries Service, Southeast Fisheries Science Center, Charleston Laboratory, Charleston, SC. Page 13 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 likely causative factors were exposure to pollutants generated by the operation of a local factory in the region and/or by exposure to pesticides in agricultural runoff, both resulting from unusually heavy rainfall in the area. Your goal: Determine the exact causative factor of death by performing a Chemical Analysis of the aqueous extract of the tissues received. CASE III (IIIA, IIIB, and IIIC) THEME: HAZARDOUS CHEMICALS IDENTIFICATION Description: The Environmental Health and Safety Department at Columbia University contacted a chemical waste disposal company to dispose of a series of unlabeled vials located in the hood of an Organic Chemistry Research Laboratory in the Department of Chemistry. Disposing of unlabeled chemicals is extremely costly to the University because the waste disposal company has to first characterize the unknown substances to properly dispose of the chemicals. The vials contain liquid and solid samples. In an attempt to save costs, the Director of Research of the Chemistry Department proposed to the Undergraduate Program to analyze the unknown samples in the instructional laboratories. Your goal: Analyze the samples (either IIIA, IIIB, or IIIC) and produce a Chemical Analysis report for the waste disposal company. Page 14 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 BIBLIOGRAPHY INTRODUCTION Considine, D. M., and G. D. Considine, ed. Van Nostrand’s Scientific Encyclopedia. 8 th ed. Van Nostrand Reinhold: New York, 1995. Felder, R. and R. Brent. ERIC Document Reproduction Service Report ED 377038 (1994). Johnson, D. W., R. T. Johnson, and K. A. Smith. Cooperative Learning: Increasing College Faculty Instructional Productivity. ASHE-ERIC Higher Education Report No. 4. George Washington University, 1991. PLANNING AND WORKING IN THE LABORATORY Avila, L. and D. Schiering. Infrared Spectroscopy Basic Techniques and Experiments. PerkinElmer, 1993. CRC Handbook of Chemistry and Physics. Latest edition. CRC Press. CRC Handbook of Laboratory Safety. Latest edition. CRC Press. Fieser, L. and K. L. Williamson. Organic Experiments. 5th ed. Heath: New York, 1997. Laboratory Manual (CHEM C2507, SPRING 1999), Intensive General Chemistry. Department of Chemistry, Columbia University, 1999. Mayo, D. W., R. M. Pike, and S. S. Butcher. Microscale Organic Laboratory. 2nd ed. John Wiley & Sons: New York, 1989. Pavia, D. L., G. M. Lampman, and G. S. Kriz. Introduction to Organic Laboratory Techniques. 3rd ed. Saunders College Publishing: New York, 1988. Shriner, R. L., et al. The Systematic Identification of Organic Compounds, A Laboratory Manual. 6th ed. John Wiley & Sons: New York, 1980. Skoog, D. A. and J. J. Leary. Principles of Instrumental Analysis. 4 th ed. Saunders College Publishing: New York, 1992. Skoog, D. A., D. M. West, and F. J. Holler. Fundamentals of Analytical Chemistry. 6th ed. Saunders College Publishing: New York, 1992. CASE STUDY PROJECTS Colbert, Ann. Forensics Program, National Marine Fisheries Service, Southeast Fisheries Science Center, Charleston Laboratory, Charleston, SC. Page 15 of 16 COLUMBIA UNIVERSITY CHEM C2507, SPRING 1999 SUPPORT INFORMATION Luis Avila Professor of Chemistry 455 Chandler Hall, [email protected] Office Hours: by appointment Alan Szeto Administrative Coordinator, Tuesday Instructor 859 Chandler Hall, [email protected] Office Hours: Thursdays, 12:30 – 2:00 p.m., and by appointment Guanglu Ge Tuesday Instructor 308 Havemeyer Hall, [email protected] Office Hours: Tuesdays, 11:00 a.m. – 12:00 p.m. Tatyana Igumenova Monday Instructor 308 Havemeyer Hall, [email protected] Office Hours: Fridays, 2:00 – 3:00 p.m. Jiang Jiang Monday Instructor 308 Havemeyer Hall, [email protected] Office Hours: Wednesdays, 3:00 – 4:00 p.m. Rebecca Kwaan Tuesday Instructor 308 Havemeyer Hall, [email protected] Office Hours: Wednesdays, 3:00 – 4:00 p.m. Alvaro Mercado Monday Instructor 855 Chandler Hall, [email protected] Office Hours: Wednesdays, 3:00 – 4:00 p.m. Chempreps (304 Havemeyer Hall) Hours: Mondays – Fridays, 10:00 a.m. – 6:00 p.m. Chemistry Library (4th floor Chandler Hall) Hours: Mondays – Thursdays, 9:00 a.m. – 9:00 p.m.; Fridays, 9:00 a.m. – 5:00 p.m.; Saturdays, 12:00 p.m. – 5:00 p.m.; Sundays, 2:00 p.m. – 6:00 p.m. MacLab (310 Havemeyer Hall) Hours: Mondays – Fridays, 10:00 a.m. – 5:00 p.m. Page 16 of 16
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