Laboratory Syllabus, CHEM 331, Fall 2003

SCHEDULE OF EXPERIMENTS AND ACTIVITIES
 
 

Week	Date	Experiment to Be Done With Links to Some Details	Preparation: Read from Z=Zubrik, MM=McMurry	Reports, Problems and Exams
1	Sep 1-2	Labor day -- no lab	Syllabus
2	Sep 8-9	Solvents, Splashes, Safety and Disposal, Safety Aide and Locker Assignments, using ISIS and Excel, Lab Check-in	Safety Rules & SOPs, Syllabus; Z 1, 2, 3; MM 2 (review polarity)
		Purification and Characterization
3	Sep 15-6	Expt 1a and 1b. Purification and Characterization of Solids: Melting Points and Solubilities	Z 1, 2, 9, 12, 13, 17, 18; Expt. 1,	Prelab Questions, Expt.1
4	Sep 22-3	Expt 1b and 1c. Purification of Solids by Recrystallization, Analysis by MP	Review Z 7, 12, 13
5	Sep 29-30	Expt 2a. Purification of Liquids by Distillation	Z 4, 17, 18, 19, 20 (class 1 & 3); Expt. 2	Prelab Questions, Expt. 2
6	Oct 6-7	Complete Expt 2b. Introduction to Chromatography, Analysis of Distillation Fractions by Gas Chromatography	Z 26(27), 30(31), 31(32), 35(36)
7	Oct 13-4	Expt 3. Column and Thin-Layer Chromatography	Z 26(27), 27(28), 28(29)	Report Expt. 1
		Structural Analysis of Pure Materials
8	Oct 20-1	Expt 4. Identification of an Unknown Liquid Mass Spectrometry AND Infrared Spectroscopy	MM 12; Z 3, 7, 33(34); Expt. 4	Report Expt. 2
9	Oct 27-8	Expt 4. Identification of an Unknown Liquid Introduction to 1H NMR Spectroscopy	MM 13; Z 3, 7, 25(26), 34(35)	Report Expt. 3
10	Nov 3-4	Expt 4. Identification of an Unknown Liquid NMR Problems	Expt. 4	NMR Problems
11	Nov 10-11	Expt M. Molecular Models & Molecular Geometry. Complete Expt 4.	MM 9	Report Expt. M
		Synthesis and Mechanisms
12	Nov 17-18	Expt 5. Nucleophilic Substitution	Z 7, 9, 10, 15, 17, 22(23); Expt. 5	Prelab Questions, Expt. 5; Report Expt. 4
13	Nov 24-5	Expt 6. Dehydration of an Alcohol; Characterization of Products from Expt. 5	Z 10, 11, 15, 22(23); Expt. 4; MM 7, 17	Prelab Questions, Expt. 6
14	Dec 1-2	Complete Expt 6. Infrared Spectroscopy, Gas Chromatography / Mass Spectrometry	Z 31(32), 33(34); MM 12, 13	Spectroscopy Lab Exam; Report Expt. 5
15	Dec 8-9	Checkout, Lecture Review Session	MM 1-12, 17, 18, Z 1-4, 7, 9-13, 15-20, 22(23), 25-28(26-29), 31(32), 33-35(34-36)	Techniques Exam; Sample Exam; Report Expt. 6

REQUIRED PURCHASES

James W. Zubrick, The Organic Chemistry Laboratory Survival Manual - A Student's Guide to Techniques, 5th edition. John Wiley and Sons, 2001. The 4th edition is OK if you have it, since the chapter numbers are the same as the 5th; since the 6th edition has one more chapter, its chapter numbers are in parentheses when different.

EXPERIMENTS (required): CHEM 331 Laboratory Experiments, Dr. Sweeting (available from Copies+, Cook Library lobby)

ALSO REQUIRED:

1. Laboratory Notebook - National 43-647 or Jones and Bartlett ISBN 0-86720-877-5 or ISBN 0-7637-0163-7, or Hayden-McNeil (available from Chemistry Club). Pages must be pre-numbered in pairs and you must be able to turn in (carbon) copies of your work at the end of the lab if necessary.  You will fill a notebook between 331 and 332, so buy a new one.
2. Goggles meeting ANSI standard Z-87 for chemical splash protection, available from Bookstore, Student Affiliates of ACS (student chemistry club). Goggles should fit the face snugly and have baffles over ventilation; hardware dust goggles with fine perforations are not acceptable. Students who wear contact lenses should remember that the consequences of foreign objects, especially vapors and liquids, in eyes with contacts are much more serious than without contacts; if you have glasses that you can wear instead, do so.

1. Rubber gloves (snugly fitted). Playtex and other grocery store models are good and cheap. I wear gloves when working in the lab almost all the time. We will provide inexpensive disposable gloves.
2. Laboratory apron or coat. Don't wear your best clothes, just in case.
3. Health insurance. A cheap group policy is available to TU students.

EXPLANATORY COMMENTS ABOUT ORGANIC CHEMISTRY LABORATORY

1. Concepts to be Learned
Chemists are generally concerned with three major problems in the laboratory: identification of materials, synthesis of new materials and understanding how materials behave. Organic chemists ask all of these questions and it is the purpose of the laboratory part of this course to introduce you to some of the basic methods that are effective for answering them for the compounds of carbon. These methods are also used for inorganic and biochemical compounds with a little modification. I have listed some questions below (with some techniques used to answer them that you will learn this semester)
1. Identification of Materials: Chemical Analysis (discussed primarily in laboratory)
1. Is a given material pure? (chromatography, spectroscopy, physical constants)
2. If a material is not pure, what is its composition? (chromatography, spectroscopy, wet chemical techniques)
3. If a material is not pure, how can you purify it? (recrystallization, distillation, chromatography)
4. If a material is pure, what is it? (spectroscopy, physical constants)
2. Synthesis of New Materials (lecture and laboratory)
1. How do you make a (new) pure compound from available materials? (reagents and conditions)
2. How do you make solutions and mixtures of desired properties from available materials? (physical constants, spectroscopy)
3. How Materials Behave: Reaction Mechanisms, Physical and Chemical Properties
1. How does a material behave under chemical or physical treatment? (melting and boiling, pressure, heat, etc)
2. How does a chemical reaction occur?
3. Why does a chemical reaction occur?
2. Skills to be Learned

During the course of this laboratory, you are expected to develop the following skills, upon which your enjoyment of the lab and your grade will depend. The laboratory is designed to teach all these skills all of the time, thus you will gradually build your skills, understanding and confidence through the course.

1. Good safety habits.
2. Understanding of chemical hazards and sources of information about them
3. Good observational skills of chemical phenomena
4. Accurate recording of experimental procedures and data
5. Effective planning of experimental procedures
6. Efficient use of lab time
7. Scientific (brief, complete and effective) writing
8. Effective use of glassware and instruments, with appropriate attention to your safety and that of the equipment.
9. Understanding of theoretical and practical basis of experimental methods
10. Interpretation of experimental observations
11. Scientific curiosity and confidence in your observations
12. Understanding and implementation of waste reduction and proper disposal methods for organic materials
3. Prerequisites

Both Chemistry 110 and 111 (or equivalent). Listed below are some of the laboratory skills you are expected to have acquired in your previous chemistry courses. Review any that you have forgotten.

1. Safe use of glassware, including thermometers, and insertion of glass into rubber stoppers
2. Cleaning of glassware (I will give you additional tips)
3. Safe handling of chemicals, especially acids, bases and flammables
4. Proper disposal of inorganic reagents
5. Lighting and controlling Bunsen burners
6. Measurement of weight and volume using appropriate accuracy
7. Use and care of balances
8. Correct solution preparation
9. Calculation of weight, volume or density from the other two
10. Calculation of weight, moles or molecular weight (formula) from the other two
11. Calculation of percent yield of a chemical reaction!!! (Note: no student will pass CHEM 331-2 until they can demonstrate that they can do this calculation)
12. Appropriate use of significant figures (don't forget to acquire and record as many as you need)
13. Balancing simple chemical equations
14. Plotting graphs (recognize the independent variable)
15. Use of the Internet, word processor, and spreadsheet
4. Grading

Your instructor's goal in the laboratory is to teach you to think and work scientifically, while learning the techniques of organic chemistry and the properties of organic compounds. The skills you learn here will be useful in scientific activities of all kinds, All of the components of your laboratory grade listed below are designed to meet this goal. REMEMBER that you must pass both lecture and laboratory to pass the course. You will receive a grade on each component.

1. Attendance is required for laboratory; late arrival is not permitted. Any student arriving late for laboratory may miss the safety discussion; the instructor reserves the right to exclude a late student from activities dependent on that safety information. The instructor may elect instead to penalize by points deducted from the "Skills" grade, as timeliness is an important skill. For some experiments, there will be an end-of-lab discussion which is also required. Any student who is ill (or whatever) and cannot attend a laboratory session will be given a makeup only if a) he/she informs me during that day of the reasons and b) she/he presents a dated confirmation note from a doctor, auto mechanic, etc. before the makeup lab. Makeup labs are not always possible because of space limitations. Any student who does not complete a lab will be graded on what they have completed. All experiments must be attempted and a report submitted for a passing laboratory grade.
2. Laboratory preparation and quizzes. You are expected to study the day's experiment ahead of time so that you genuinely understand it. To encourage you to do so, you will be assigned pre-lab questions to be turned in at the beginning of the laboratory lecture; they will usually be graded and returned to you during the lab. Please try to think about the questions rather than just copying from the text; put the answer in your own words. Identical responses to prelab problems from n different students will be assumed to be copied and will be given at most 1/n of the earned grade. You may wish to write summary notes or questions on the instructions or on the left side of your lab notebook page (unless you have automatic carbon paper) or on a separate sheet to guide you. Also recommended is a brief summary of the steps enetered into the laboratory notebook and clearly labelled "PLAN", to distinguish it from the notes you take on what you actually do. With this preparation, you are much less likely to make mistakes andmuch more likely to get out early. Pay particular attention to safety (e.g. whether to use the fume hood), materials needed, and efficient use of your time. If you are doing a chemical transformation you should have entered in your notebook before entering the lab a balanced equation and a calculation of the expected yield from the reaction, but NOTHING ELSE (unless you have a PLAN). Bring your questions to the pre-lab discussion. You will periodically be given (unannounced) pre-lab quizzes to test your preparation. If you are always prepared I will not give quizzes. Students working in an unsafe manner are assumed to be inadequately prepared. Up to 8% of your grade.
3. Laboratory Reports, including notebooks. See details in E and F. About 60% of lab grade. Late reports (see due dates in schedule) receive reduced credit; no reports will be accepted after the last day of class. You must correctly calculate the percent yield of a reaction at least once to pass the course.
4. Laboratory Exam(s). A two-part laboratory exam will be given toward the end of the semester. This will be a paper and pencil exam to determine your understanding of the techniques you have learned. The exam will cover the theory and procedures of the experiments completed, safety, and spectroscopic interpretation. Details in F. Approximately 30% of the lab grade.
5. Safety aide. In order to involve you more thoroughly in the development of good safety practices, you will be assigned once to the rotating role of SAFETY AIDE. It will be your responsibility for the week assigned to:
1. Read the experiment for the week particularly carefully to anticipate potential hazards.
2. Check the toxicity and safe disposal method for each chemical to be used (references below). You must use at least one source in addition to your text. Books (see G) are available in Cook Library, the Chemistry tutoring center and the laboratory; the Internet is another powerful source. For some experiments you may make a presentation on other aspects of safety, such as glassware or instruments.
3. Evaluate and extract the most relevant information and give a presentation to the class (5 minutes) on your findings. Be sure to state your sources. If you wish to use a transparency or handout, see me the prevous day for assistance.
4. Your AIDE responsibilities will count as part of your laboratory grade, about 8%. The grade will be based on relevance, accuracy and on how successful you are at convincing your classmates to work safely. The presentations will be given during the first hour of lab (lab lecture time). During the first week of class, you will be able to choose the date and subject of your safety presentation. You may see me to find out your grade after the lab.
6. Results. Products or data will be turned in for all experiments. Products will be graded separately for both purity and yield, for about 8% of your grade.
7. Skills developed. I will spend quite a bit of time with you in laboratory and will visit you on a regular basis at your work area. My main purpose is to help and to teach, but I will take note of the physical skills you develop; up to 8% of your lab grade will be based on what you learn physically during the lab. This grade is typically very dependent on your preparation for the lab, as well-prepared students typically finish earlier with fewer mistakes. Students working in an unsafe manner are assumed not to have developed the requisite skills.
5. Laboratory Notebook
   The keeping of a laboratory notebook is probably the most important skill you will learn in this course. Good laboratory records are crucial to science, because the accuracy that other scientists and the public rely on is dependent on this primary record. Pretend Organic Chemistry Lab is original research. Treat your laboratory notebook as if it were the only record anywhere of how to do this experiment, as if no one had ever done this experiment before. The notes you take should be sufficiently detailed so that anyone (including yourself 10 years from now) can take your notebook and repeat the experiment using your notes and know exactly what to do and what will happen. Because science requires absolute honesty in observation and report, no deliberate misrepresentation of an experiment will be tolerated; fabrication of data will result in an F in the course.
   The logistics of research notebooks vary somewhat in the real world. The requirements here are common in both industrial and academic chemical and drug research. Page 1 will be a table of contents. Each new experiment will start on a new page and the date will be entered each day you work in the lab (the time between working days may be important). If you have an unfinished experiment when you start the next one, leave a page for completion. If you must continue on a non-contiguous page, include "continued from" and "continued to" references. The notebook you will use will provide carbon copies. As you work in the lab, you will keep carbon copies of your work; you will turn these in to me as part of your report (that way, you can keep working while I am grading). In research they would be stored in a separate location for security.
   When you come into the lab, you should have entered in your notebook title, date and, whenever you do a chemical reaction / synthesis, balanced equation and calculations of expected yield and any important physical properties of the reagents; you may use the lab text method of organizing physical data, or list it under the balanced equation. In most cases the title will serve as a "purpose" or "introduction". A brief plan (clearly labelled as such) may be entered before class, but DO NOT COPY TEXT PROCEDURES INTO YOUR NOTEBOOK BEFORE CLASS. Notes from lab lectures should NOT be in your laboratory notebook. Your laboratory notebook serves as a diary, a log, of your laboratory activities and your interpretation of them (clearly labelled as interpretation). No laboratory notebook entries, except plans and calculations, should ever be done outside of the lab.
   As you work in the lab, record in your notebook everything you do and see in your own words as you do it, making copies as you do. Lab notes must NEVER be taken on scraps of paper. I will confiscate and destroy these scraps. Do not copy the instructions--I've read those already and consider this plagiarism. Incomplete sentences are allowed, as is the first person, as long as the meaning is clear. You may use a list format instead of paragraphs; in either case, make sure you have some logical breaks. Subtitles are encouraged (e.g. synthesis, neutralization, purification). Since you will have plenty of time for taking lab notes, they should be reasonably neat.
   The detail recorded for a particular procedure will vary throughout the semester as your knowledge and skills improve. For example, the first experiment is devoted to the process of recrystallization and will probably take 2-3 notebook pages to describe. During second semester, this whole process may be summarized this way: "recrystallized the 0.70 g yellow crude product from 20 mL boiling 95% ethanol (with charcoal treatment and hot filtration) by cooling to yield 0.50 g (71%) pale yellow needles, m.p. 117-119oC."
   Any new apparatus you use should be sketched (with labels) when you set it up (do not copy from the text but from your own apparatus.)
   Observations and procedures will be completely integrated since you will write things as they happen; be sure to record any errors, repeats, etc. since I often remember them. Nothing should ever be obliterated from a lab notebook and pages should never be removed. If your record does not reflect what you actually did, cross out the error neatly and rewrite - you may need the information later! If you did the wrong thing, the notes should remain with a strong notation that this was an error (you may prevent repeat errors). Your lab notebook should be a complete and accurate diary of what happened. Learn to OBSERVE and RECORD color, physical state, temperature - especially if it changes - automatically, for every compound and mixture, plus all heating methods and settings.
   For some experiments (e.g. unknowns) it will be necessary to interpret the data as you are working, to draw conclusions, in order to decide what the next step is. Put your thought processes in your notebook, since it will help you to understand and trouble-shoot your own conclusions. But do not confuse interpretations of observations with the observations themselves. For example, if you did a test for halides, "positive" or "soluble" are conclusions, but "white precipitate formed" or "no solid visible" are observations: BOTH the observation and the conclusion should be in your notebook. If the observation is recorded you can reinterpret it if further experiments prove that a halide is unlikely (for example). As you are interpreting your data, you may also write down what you are planning to do next - make sure the plan is clearly labelled as such.
   At the end of each experiment, please state explicit results and conclusions in your notebook. The success of each chemical transformation that you perform needs to be documented, so that it is clear to the reader of your report that you have accomplished the transformation. A melting or boiling range and infrared spectrum should be determined and interpreted for each starting material and product (boiling points may be obtained during distillation or in a separate experiment); in some cases you will be given the IR spectrum of starting material to save time and materials. Spectroscopic data should be unambiguously labelled, interpreted and attached to your report. Include brief comments about the success of the experiment: the yield, physical properties and identity of the product from any chemical reaction or purification, and brief comments about sources of errors or losses. If you compare your data with the chemical literature to prove its identity, be sure to provide a reference.
   In order to help you to learn to take lab notes, your instructor will come around to look at your notebooks and make suggestions or hand out some examples. In addition, bring your notebook to your instructor for initials at the end of each laboratory period to certify that these were your notes and they were taken during the lab. Feel free to ask for advice anytime about notebooks.

6. Laboratory Reports
One week after you have completed each experiment you will be required to turn in the following (details are given below the list):
1. Abstract (no carbon necessary; should be on separate paper)
2. Carbon copy of lab notes with supporting data sheets from spectrometer or chromatograph.
3. Post-Lab problems (no carbon necessary; should be on separate paper)
4. Pre-lab problems which have already been graded and returned to you.
5. Products, for some experiments.
Items 1, 2, 3 and 4 should be stapled together in that order. These will be graded and returned to you 1-2 weeks later. Because most of your grade depends on the laboratory notes, and you will receive feedback during the labs on these (ask for my input if I don't visit you); you should not wait until the lab is returned to modify any methods that you are using that I have criticized. Products will be turned in separately during a laboratory period; please do not take your samples home.

1. Abstract

"that which presents the substance or general idea in brief form; concise; condensed" - Webster's New World Dictionary

When the experiment is completed, you will make a summary or abstract of the whole experiment, 2 -3 sentences, which describes the purpose, procedures and results (not in your notebook). You may wish to use a short table to present physical data on your products. Use your best writing skills: you will be graded on conciseness and accuracy. The purpose of this abstract is to guide the reader to the important parts of the full record; it is not a "purpose" but a "summary". Abstracts serve this same function in peer-reviewed reseeach papers.
2. Carbon copies of notebook pages.

Note that you must start each new experiment on a new page to be able to turn in the notes one experiment at a time. Do not turn in originals.

3. Pre- and Post-Lab Problems

You will regularly be assigned problems from your lab texts to be turned in with the experiment. You may consult with each other in the solution of these problems, but DO NOT copy each others' solutions: your grade will be lowered in proportion to the number of identical problem sets like yours.

4. Products

For some experiments you will turn in your products for grading; these will count no more than 20% of the grade on the experiment. The products will be graded for yield and purity. No credit will be given for inadequately identified materials. Each must be labelled with the following:

• Your name, course and section number
• Name or number of compound
• Number of grams
• % yield
• Melting range or boiling range
• Instructor's name
5. Notes on Specific Experiments, Procedures and Lab Reports

Facilities at TU: Each of you will be assigned a personal locker which you will share with another student in your section. In addition, we share community equipment among all the sections of organic chemistry. You will be given lists of what belongs where (in general, ground glass equipment, heating and filtering apparatus are community). It is important that you clean and return all the community equipment to its correct location so that other students can do their experiments. Your instructor reserves the right to take points off your lab reports if you are regularly careless about community equipment.

Experiment I. Recrystallization and Melting Point. Complete the prelab questions. You will be given an impure compound to purify and identify. Using individual and mixture melting points, you will be able to identify 1 - 3 others in the class who have the same unknown and work together to determine the best solvent. Allow the samples to dry in your locker, being sure to label it well (remember, you share a drawer). Note that the experiment is due 2 weeks after it is scheduled to be completed to ensure that your samples are dry enough to weigh and determine the melting point. Turn product in with correct label (See F4). Don't forget the postlab problems.

Experiment 2. Distillation. Groups will do the distillation in different ways, and transfer data within the group during the laboratory period. Remember the person finished first is the person who will collect the data from all and plot it with Excel. Label your graphs with the kind of distillation. Fractions from the distillation will be analyzed during the second week of the experiment by GC. Make sure yours are labelled adequately (remember, you share a drawer). Questions within the procedures are designed to help you understand the procedure as you are doing it; you should be able to answer them on a laboratory exam. Postlab problems and all graphs, but no samples will be turned in.

Experiment 3. Chromatography of organo-iron compounds shows why the name of the technique is based on the Greek word for color. You will separate by column chromatography and analyze by thin-layer.

Experiment M. Models: The purpose of this experiment is to provide an opportunity for you to practice using molecular models and exploring conformation and configuration. Report requirements will be decribed at the time; you will not be doing this in your laboratory notebook, but you will need it for the other activities on those days. This report is due on the same day the experiment is completed.

Experiment 4. Identification of an Unknown: In these experiments, instead of an abstract, write a summary (as long as you need) of what you believe your compound is and why. You will need to interpret your spectroscopic data, and compare it to that expected for this compound and/or that found in the literature for this compound (don't forget references - always give credit to your sources). Some of the analysis should be in your notebook.

Experiment 5. Nucleophilic substitution, Preparation of 1-Bromobutane: Prelab questions. Be sure to interpret your spectral and chromatographic data.

Experiment 6. Dehydration of an Alcohol, 2-Methylcyclohexanol. This reaction produces several products. You will compare the IR spectrum of reagent and product to determine whether conversion has occurred and you will be provided GC/MS data to identify the products.

Techniques Laboratory Exam: This part of the laboratory exam will test your recollection of everything but spectroscopy. For example: safety and chemical hazards, theory of melting, boiling, and distillation, procedures for experiments (reflux, extraction, etc, methods but not amounts), apparatus, etc. It may be open notebook, so your notes may have additional importance.

Spectroscopy Laboratory Exam: This part of the exam will test your understanding of spectroscopic methods and ability to interpret spectroscopic data. Most of the exam will consist of problems in which you determine the structure of a compound whose IR, NMR and MS are given, perhaps along with other information. There will be generous opportunities for choice on the exam; spectral absorption tables which you have already used will be provided.

7. References

These sources may be of use to you and may be found in the library (reference, faculty reserve room or stacks), chemistry tutoring center, in the laboratory itself or on the World Wide Web.

GENERAL LABORATORY TECHNIQUES, CHEMICAL TESTS AND DATA

1. Writing the Laboratory Notebook, H. M. Kanare, ACS, Washington, D.C., 1985. This book provides both rationale and methods for keeping a laboratory notebook that will satisfy the patent office, your boss, and yourself.
2. The Organic Chem Lab Survival Manual; A Student's Guide to Techniques, J. W. Zubrick, John Wiley and Sons, NY 1988. This book manages to be entertaining while explaining the basics of organic lab techniques. Excellent instructions for laboratory notebook .
3. Organic Laboratory Techniques, R. J. Fessenden and J. S. Fessenden, 2nd ed., Brooks/Cole Division of Wadsworth Publishing, Belmont, CA 1993. All the basic lab techniques are here. Excellent discussion of MSDS's
4. Experimental Organic Chemistry: Principles and Practice. L. M. Harwood and C. J. Moody, Blackwell Scientific Publications, Oxford, 1989. Especially good on how to keep a notebook and wet chemical techniques. A manual that would take you through graduate school in organic chemistry, but accesible to the beginner.
5. Laboratory Experiments in Organic Chemistry, 7th edition, R. Adams, J. R. Johnson and C. F. Wilcox, Jr., Macmillan Pub. Co., Inc., New York 1979. Old text with good stuff.
6. The Systematic Identification of Organic Compounds, 5th edition, R. L. Shriner, R. C. Fuson, D. Y. Curtin and T. C. Morrill, John Wiley & Sons, Inc., New York 1980. The best source for wet chemical tests for functional groups.
7. Handbook of Tables for Organic Compound Identification, Z. Rappoport, CRC Press, Cleveland 1964. Huge tables of compounds sorted by functional group and melting and boiling points.
8. Vogel's Textbook of Practical Organic Chemistry, B. S. Furniss et al., Longman, Inc., NY 1978. The old standard reference updated a little.
9. Handbook of Organic Chemistry, J. A. Dean, McGraw-Hill, NY 1987.

SPECTROSCOPIC TECHNIQUES

Your lecture text has excellent discussions of the theory and use of spectroscopic techniques. In addition, software available in the tutoring center, and on the Internet - World Wide Web may be helpful, and other books with more detail.
1. irtutor, dynamic software written by an organic chemistry graduate student which summarizes theory at basic and quantum mechanical levels and shows molecular motions responsible for a wide variety of IR bands. Not enough functional groups, but otherwise a dynamite piece of software. Wish we had more this good. Do not miss this one!!
2. "NMR Tutor" is more like a set of slides from a lecture class, but explains basics well. Different author from irtutor.
3. Links to educational NMR software in various places can be found in a terrific web site at the University of Umea (Sweden), http://www.anachem.umu.se; NMR stuff is at http://www.chem.umu.se/division/fk/EduNMRSoft.html
4. Spectrometric Identification of Organic Compounds, 3rd edition, R. M. Silverstein, G. C. Bassler and T. C. Morrill, John Wiley & Sons, Inc., New York 1981. This is probably the best book around for organic chemistry. Oledr editions are fine but may not have C-13 NMR.
5. Introduction to Spectroscopy, D. L. Pavia, G. M. Lampman and G. S. Kriz, Jr., W. G. Saunders Co., Philadelphia 1979. The second best.
6. Organic Structural Analysis, J. B. Lambert, H. F. Shurvell, L. Verbit, R. G. Cooks, G. H. Stout, MacMillan, NY 1976. There is also a more recent edition which is more accessible.
7. The Spectrum in Chemistry, J. E. Crooks, Academic Press, London 1978.
8. The Chemist's Companion, A Handbook of Practical Data, Techniques & References, A. J. Gordon & R. A. Ford, Wiley. This is a great reference for lots of things - all of the stuff I ever wanted in the CRC Handbook that wasn't there, like pKa's, spectroscopic data.
9. The Aldrich Library of Infrared Spectra, C. J. Pouchert, Aldrich Chemical Co., Milwaukee 1970. Lots of spectral data for comparison.
10. The Aldrich Library of NMR Spectra, C. J. Pouchert, W. R. Campbell, Aldrich Chemical Co., Milwaukee 1974. Lots of spectral data for comparison - H-1 only.
11. Merck IR Atlas (FTIR), VCH Publishers Inc., NY 1987.

SAFETY

1. Excerpts from Genium's safety publications. Thorough and entertaining.
2. General laboratory safety, including design, from Flinn Scientific, which produces lots of educational materials for high school labs.
3. Material Safety Data Sheets, MSDS's, flyers from chemical companies which accompany chemical products, in accordance with the OSHA worker right-to-know law. These may be found, alphabetically by IUPAC name, or searchable by IUPAC name, on the World Wide Web. Several sites I have found to be useful (there are probably others):
• What is an MSDS? Genium, the company that created this, sell MSDS's, so you can't get them from their web site.
• MSDS's from the University of Vermont and the links it maintains to other sources of MSDS's and other safety information.
• Interactive Learning Paradigms Incorporated's list of WWW resources for MSDS's, including an explanation of what they are, definitions of terms and parameters, book list and regulations.
• Oxford University's collection of MSDS's
• MSDS's from Fisher Scientific: Search either the Acros Organic or Fisher Chemical Catalog for the compound; the description will include a choice for MSDS.
• Cornell University MSDS collection, searchable by typing in the name.
• The University of Georgia's Public Safety Division has links to a large number of universities and companies which have MSDS's posted as part of their commitment to Right-To-Know laws.
• Enviro-Net MSDS's. Search using alphabetical groups.
• Updated links to these and other sites.
4. Hugh B. Kareful, Working Safely with Chemicals in the Laboratory: A Student Guide, Genium Press, Schenectady, NY 1994. An amusing booklet with just about everything you need to know to work with chemicals. An extract about MSDS's is on the Web site above.
5. Safety in Academic Chemistry Laboratories, American Chemical Society, 1974-6. A thorough booklet with general guidelines for students and faculty, but no specific toxicity information.
6. The Merck Index. An Encyclopedia of Chemicals and Drugs, 8th-10th edition, Merck & Co. Toxicity information on drugs and many common compounds whose toxicity has been studied. More recent editions have more compounds and less information for each.
7. Aldrich Catalog/Handbook of Fine Chemicals, Aldrich Chemical Co. Basic information and references on the compounds they sell - which is lots.
8. Sigma-Aldrich Library of Chemical Safety Data, Edition II, R. E. Lenga, Ed., Volumes 1 and 2, Sigma-Aldrich Corp., Milwaukee, WI, 1988. This bookis very popular with students looking things up because of its convenient tabular format.
9. Registry of Toxic Effects of Chemical Substances, NIOSH, Govt. Printing Office, Washington, 198O. The official blurb.
10. Dangerous Properties of Industrial Materials, Sax, N. I., Reinhold, New York, 1984 (6th edition).
11. Handbook of Toxic and Hazardous Chemicals and Carcinogens, Sittig, M., Noyes Publications, Park Ridge, NJ, 1985.
12. Handbook of Reactive Chemical Hazards, Bretherick, L. Butterworths, Boston, 1979 (2nd edition). Things that go bump in the night, and things you should never mix.
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24. First Aid Manual for Chemical Accidents, Lefevre, Dowden Hutchinson & Ross, Stroudsburg, 1980.
25. Fire Protection Guide on Hazardous Materials, National Fire Protection Association, Boston, 1975.
26. Hazardous Chemical Data Book, Weiss, Noyes Data Corp., Park Ridge, 1980.
27. Chemistry of Hazardous Materials, Meyer, Prentice-Hall, Englewood Cliffs NJ, 1977.
28. Safe Storage of Laboratory Chemicals, Pipitone, John Wiley and Sons, NY 1984.

Revised July 20, 2001, LMS