2. Experiment Schedule

Table abbreviations:

In the schedule above, the following abbreviations are used: McM = McMurry, Organic Chemistry; Zub = Zubrick, The Organic Chem Lab Survival Manual and MOE = Microscale Organic Experiments, created by the Towson University Organic faculty (some customization for each instructor); all three of these books are required for the course

REQUIRED:

1. 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 also satisfactory, and the chapter numbers are the same. The 6th edition is also satisfactory; since it has one more chapter, 6e chapter numbers are in parentheses. Known as "Zub" in this syllabus. Please note that some reading assignments in Zubrick are repeated; almost every time a technique is used, the appropriate section is assigned for review. Please read it carefully the first time and look it over the second time for review.

2. Chemistry 332 Laboratory Microscale Organic Experiments, prepared by the TU faculty and staff, available from Copies+ in the library lobby. Slight differences in experiments, prelab questions, etc. mean that each instructor publishes their own collection of experiments; be sure you get the one labelled Dr. Sweeting. Known as "MOE" in this syllabus.

3. Laboratory Notebook - National 43-647, Jones and Bartlett (ISBN 0-86720-893-7 or 0-86720-877-5), or Hayden-McNeil or Chemical Education Resources Organic Chem Lab Notebook (ISBN 0-87540-252-6), or equivalent; the notebook must have pre-numbered pairs of pages and create carbon copies so that you can turn in copies of your work without turning in your notebook. Notebooks are available from University Store or Student Affiliates of ACS (SAACS, Chemistry Club) You may continue in your CHEM 331 notebook if you used only about half of the pages.

4. Goggles meeting ANSI standard Z-87 for chemical splash protection, available from University Store or Student Affiliates of ACS (SAACS, Chemistry Club). Goggles must seal to the face and have baffles to prevent splashes from entering the eyes. 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. Avoid wearing contact lenses in the lab.

5. McMurry, Organic Chemistry, your lecture text, known as McM in this syallabus.

STRONGLY RECOMMENDED:

1. Rubber gloves (snugly fitted). Playtex and other grocery store models are good and cheap, and far better than the ones we provide. Treat your gloves like bare hands - keep them clean to ensure that you do not transfer chemicals to your notebook, or your face. I also recommend that you select a pen to keep in the laboratory so that you will not accidentally transfer chemicals to your mouth if you use it at home.

2. Laboratory apron or coat. This protects your clothes and your skin.

3. Health insurance. If you do not already have some, the University makes it available at very reasonable rates.

1. Scope and Purpose

Chemists are generally concerned with three major problems.

1. Analysis
1. Is a given material pure?
2. If a material is pure, what is it?
3. If a material is not pure, what is its composition (qualitatively and quantitatively)?
4. If a material is not pure, how can you purify it?
2. Synthesis
1. How do you make a (new) pure compound from available materials?
2. How do you make solutions and mixtures of desired properties from available materials?
3. Mechanism/Properties
1. How does a material behave under chemical or physical treatment?
2. How does a chemical reaction occur?
3. Why does a chemical reaction occur?
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. Most of the experiments this semester will be synthetic, with analysis of the products of your syntheses. During the course of this laboratory, you are expected to develop the following skills:
1. good observational skills of chemical phenomena
2. accurate recording of experimental procedures and observations
3. scientific curiosity and confidence in your observations
4. planning of experimental procedures
5. efficient use of lab time
6. manual dexterity with glassware and instruments
7. good safety habits
8. understanding of experimental methods
9. interpretation of experimental observations
10. brief, complete and effective writing to communicate science
The laboratory is designed to teach all these skills all of the time, thus you will gradually build your skills and understanding and confidence through the course.

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2. Prerequisites

You must have completed CHEM 110 and 111 and CHEM 331, preferably with a C or better.

Laboratory skills you should have learned in CHEM 110-1:

1. safe use of glassware, including thermometers, insertion of glass into rubber stoppers
2. cleaning of glassware
3. safe handling of chemicals, especially acids, bases and flammables
4. lighting, controlling, and safe use of Bunsen burners
5. measurement of weight and volume using appropriate accuracy
6. use and care of balances
7. correct solution preparation
8. calculation of weight, volume or density from the other two
9. calculation of weight, moles or molecular weight (formula) from the other two
10. calculation of percent yield of a chemical reaction
11. appropriate use of significant figures (don't forget to acquire and record as many as you need)
12. balancing simple chemical equations
13. plotting graphs (recognize the dependent variable)
Laboratory skills you should have acquired in Organic I, CHEM 331:
1. safe handling of flammable liquids
2. proper disposal of waste organic compounds and ways of minimizing waste
3. assembly and use of round-bottomed flasks and ground glass joints for distillation and reflux
4. requirements and procedures for a research notebook
5. purification by recrystallization of an unknown solid
6. purification by distillation of a liquid
7. analysis of purity by gas chromatography
8. preparation of liquid sample and operation of infrared spectrometer
9. interpretation of infrared spectra
10. interpretation of proton nuclear magnetic resonance spectra
11. interpretation of toxicity and other safety information
If you are uncertain of any of these procedures or skills, please ask your instructor for assistance before attempting any of them. Some I will review briefly during Organic II as you need them.

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3. Preparation and Post-Laboratory Discussion
1. PREPARATION. Your preparation for laboratory will determine how much you learn from it, and how successful your experiment is. Study the experiment and, of you wish, make a plan in a form that is more convenient for you than the instructions. Have the overall plan stored in your head, so that you will not lose track of where you are going. Any planning notes you place in your laboratory notebook should clearly be labelled as such. Awareness of safety issues is a key part of your preparation.
If you are doing a chemical transformation you should have entered in your notebook before entering the lab: a balanced equation for the reaction, molecular weights, number of moles and grams of each reagent and product and a calculation of the expected yield from the reaction. Note that if you are working with a liquid, it is very important to know the density to ease any weighings you may have to make.
Pre-laboratory questions may be assigned for some or all experiments. They will be graded and returned before the experiment is due. Please be sure that you correct any misunderstandings that you may have shown in the pre-laboratory questions in your discussion of the experiment, whether there are post-laboratory questions or not. See grading of reports below.
2. POST-LABORATORY DISCUSSION. For some experiments we will have a post-laboratory discussion, to be held in the last 0.5-1.0 hour of the laboratory period. We will discuss the outcomes and significance of the experiment. You are expected to be there - you will find these discussions helpful in interpreting your data and preparing for the laboratory exam.
Your laboratory notes will include written discussion of the results of the laboratory; see grading of reports below.

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4. Grading

Your instructor's goal in the laboratory is to teach you to think, work and record your activities scientifically, while learning the techniques of organic chemistry. 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. Your grade will depend on the following aspects of your work, in decreasing order of importance.

1. Attendance is required for all laboratory periods, including the pre-lab lecture. Late arrival is not permitted; any student arriving late for laboratory may miss the safety discussion and the instructor reserves the right to exclude that student from the lab. 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 before or during that day of the reasons and b) she/he presents a dated note from a doctor, auto mechanic, etc. attesting to these reasons. Makeup labs are not always possible because there may not be space in another lab. All students must attempt every experiment. Any student who does not complete a lab will be graded on what they have completed. There are no points for attending, but you can fail the course if you do not do so.
2. Laboratory preparation, prelab questions and quizzes.

You must arrive prepared for the laboratory, i.e. with notebook, goggles, appropriate lab text(s) or instructions and adequate preparation. Any student who arrives unprepared WILL NOT be allowed to do the experiment except under exceptional circumstances. You may keep both notebook and goggles in your locker, taking only the carbon copies home to work on reports. In the real world, laboratory notebooks are not allowed to leave the laboratory. In keeping with good record-keeping principles, I keep my research notebook in the lab and take only the copies home; the copy at home is used to work on papers and serves as a backup against fire or other loss.

You are expected to study the day's experiment ahead of time so that you genuinely understand it; you may wish to make planning note in your lab notebook, clearly labelled as such. With this preparation, you won't waste valuable lab time re-reading the experiment and you are much less likely to make mistakes. Pay particular attention to safety (e.g. should you use the fume hood?), materials needed, how you will transfer and measure, and efficient use of your time. Bring your questions to the pre-lab discussion. You may be assigned pre-lab problems; theses do not go in your notebook. 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 will periodically be given (unannounced) prelab 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 10% of your grade.

3. Laboratory Reports. They include laboratory notebooks (quality, not quantity), abstracts and analyses of results. Late reports receive reduced credit (one letter grade for every 2 days late); no reports will be accepted after the last day of class. You must correctly calculate percent yield to pass the course. See details in E, >65% of lab grade. Your will receive a letter grade or a numerical grade or both; the scale is A:20; A-:19; B+:18; B:17; B-:16; C+:15; C:14; C-:13; D:11.
4. Laboratory Exam. A laboratory exam will be given toward the end of the semester. There may be two exams, one on experiments and one on spectroscopic interpretation. This (these) 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. The spectroscopic problems in McMurry would be a good place to go for practice. 15-20% of lab grade.
5. Safety Aide. In order to involve the students in this class more thoroughly in the development of good safety practices, I am establishing a rotating assignment of SAFETY AIDE. It will be the responsibility of the student(s) appointed SAFETY AIDE for the week 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 book or Internet source in addition to your text. Books and Internet access are available in Cook Library and the Chemistry tutoring center.
3. Extract the relevant safety information for the experiment you are doing and give a presentation to the class (5 minutes) on your conclusions. For example, you do not need to discuss exposure to dust when you will be working with a dilute solution.

These AIDE responsibilities will count as part of your laboratory grade, about 8%. The grade will be based on accuracy, relevance and on how successful you are at convincing your classmates to work safely. The presentations will be given at the beginning of the lab lecture for that experiment. 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. A: accurate and appropriate information presented in a clear manner; B: accurate information but some irrelevant; C: information not adequately edited for the experiment; D: muddled and confused; NO CREDIT will be given for late work.
6. Results. Products or data will be turned in for all experiments. Products will be graded separately for both purity and yield, for about 10% of your grade.
7. Skills developed. I will visit you frequently 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 10% 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..

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5. Laboratory Reports

One to two weeks after you have completed each experiment you will be required to turn in the items below as your laboratory report. You are encouraged to turn in laboratory reports as soon as possible after all the data has been collected; additional time has been allotted for drying and characterization of products.

1. Abstract (no carbon necessary).
2. Carbon copy of lab notes with spectrometer or chromatograph output and interpretation / conclusions.
3. Problems or Postlab Questions (no carbon necessary).
4. Products when requested.

Items 1, 2, and 3 should be stapled together in that order, with any instrument output attached (interpreted); both graded prelab questions and ungraded postlab questions should be submitted. The collection will be graded and returned to you 1-2 weeks later. Because most of your grade depends on your notes, and you will receive feedback during the labs on these; you should not wait until the lab is returned to modify any methods that you are using that I have been critical of. The report pieces should have the following properties:
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 (less than one-half of a typed page, 2 -3 sentences). In about three sentences, summarize the purpose, procedures and results, including physical data on your products. You will be graded on conciseness and accuracy and must use the English language correctly. The purpose of this abstract is to guide the reader (your instructor in this case) to the important parts of the attached notes. It must not be in your notebook, but on a separate page attached to the front of the entire report.
Nothing should appear in your abstract that is not also in your notebook in considerably more detail.
2. Notebook:
1. Principles
Pretend that you are doing research and that no one has ever done this experiment before. The notes you take should be sufficient so that anyone (including yourself 10 years from now) can take your notebook and repeat the experiment and know exactly what to do and what to expect. You are to treat your laboratory notebook as if it were the only record anywhere of how to do this experiment. You may refer to details in another experiment in the same notebook if you repeat a common technique, but any changes must be noted.
In an industrial or research lab, notebooks would never leave the lab, and might even be locked up when you leave the building. They would always be cosigned by a knowlegeable colleague or supervisor to establish their veracity (for example, for a patent). Moreover, they are the property of the company or other institution.
Because science requires absolute honesty in observation and report, no deliberate misrepresentation of an experiment will be tolerated; fabrication of the data record will result in an F in the course.
2. Mechanics
Don't forget, your are required to have goggles, notebook and appropriate text to be permitted to do the experiment. The notebook you will use should have 8-1/2 x 11" pre-numbered pages, 2 of each (i.e., 1, 1, 2, 2, 3, 3, etc.), with carbonless copies or a sheet of carbon paper. Page 1 will be a table of contents (often a page is set aside in the notebook -- use that). As you work in the lab, you will keep carbon copies of your notes; you will turn these in to me as part of your report (that way, you can keep working while I am grading). Since you will be making copies as you write, be careful to move the carbon paper in the National notebook or the heavy cardboard in the "carbonless" notebooks to prevent accidental copies. Many of the notebooks have a bold line down the middle of the page: ignore this line. Student often think they should put procedures on the left and observations on the right; although that approach might have the salutarious effect of encouraging observations, it has been my experience that trying to create two columns seldom does more than create a confusing notebook in which the reader cannot decipher whether the story continues across or down (with most people it alternates). Write straight across the pages as if the lines were not there.
Lab notes must NEVER be taken on scraps of paper. I will confiscate and destroy these scraps.
Start each new experiment on a new page and enter the date each day you work in the lab (the time between working days may be important). You do not have to start a new page for each day, just for each experiment. In a research, development or applications lab, you would sign each page and have it cosigned by a colleague or supervisor each day. Please at least put your initials on each page and your name on the first page of the experiment. I will be the cosigner of your laboratory notebooks. Do not leave the lab without my initials in your notebook to indicate that this is the work you completed and recorded on this day.
Planning notes or abbreviated outlines may be included if clearly labelled as such but procedures may not be entered until you have actually completed them. Notes from lab lecture may NOT be included in your lab notebook.
You may leave your goggles and notebook in your locker during the week.
3. Before Lab
Mental preparation for laboratory is the major key to success. You should have a mental map, or a written outline (which may be in your notebook if it is clearly labelled as a plan) for the experiment. This preparation will ensure that you complete the lab quickly and safely. See above for practical details.
When you come into the lab, you should have entered in your notebook title and date. If you are doing a chemical reaction, you should also enter balanced equation, calculation of expected yield, and any important physical properties of the reagents; you may use the lab text method of organizing masses and physical data into a table, or create a table under the balanced equation, using the sketches of structures or formulas of the reagents and products as column headings. In most cases the title will serve as a "purpose" or "introduction". A brief plan, clearly labelled as such, may be entered before the lab period, but do not copy text procedures into your notebook before (or during) class. Notes from lab lecture MAY NOT be taken in your laboratory notebook.
4. During 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; if you use paragraphs, make sure you have ample and logical breaks. Subtitles are encouraged (e.g. neutralization, purification, as they make the process clearer to both you and any other reader. Since you will have plenty of time for taking lab notes, they should be reasonably neat.
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, as there are often minor modifications.
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 heating methods and settings.
The detail recorded for a particular procedure will vary throughout the course as your knowledge and skills improve. For example, the first experiment in CHEM 331 is devoted entirely 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 powdery product from 20 mL 95% ethanol, treating with charcoal and gravity filtering hot before crystallization, to yield 0.50 g (71%) pale yellow needles, m.p. 117-119oC."
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.
For some experiments it will be necessary to interpret the data as you are working, and to draw conclusions to decide what the next step will be. You will certainly want to do this while you are working on determining the identity of an unknown. 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, and make sure you distinguish interpretation / hypothesis / conclusion from procedure and observations. For example, if you did a test for ketones, "positive" is a conclusion, but "red precipitate formed" is an observation: 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 ketone 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.
In order to help you to learn to take lab notes, I will and come around to look at your notebooks and make suggestions or hand out some examples. Feel free to ask for advice anytime about the style, content and philosophy of laboratory notebooks.
5. After Lab
At the end of each experiment, please complete any calculations and graphs, interpret any spectra or physical data, and state explicit results and conclusions in your notebook. For any calculations, be sure to show your method. These steps may be completed inside or outside of the lab. 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 (as you should), be sure to provide a reference. This part of your notebook may count up to one third of your lab grade -- do not neglect it!
Your notebook, which now has (purpose), procedures, observations and conclusions, will provide the basis for your abstract, and should help you with some of the postlab problems, both of which will be done after the lab.
3. Problems or Postlab Questions: You will regularly be assigned problems / postlab questions to be turned in before or with the experiment. Please note that any errors in your responses to any prelab questions should be researched so that your responses to any postlab questions will not have the same errors; both will be submitted with the final report. Please try not to copy from the text -- I have read it. Try to understand and put it in your own words. Identical responses from n different students will be assumed to be copied and will be given at most 1/n of the earned grade. Sometime this happens because you all copied from the text -- don't let that happen to you. You may work together figuring out the answers, but each person should turn in the answer in their own words.
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 of compound (if known)
• Number of grams
• % yield
• Melting range or boiling range
• Instructor's name

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6. Microscale. Please see the separate handout entitled Microscale Organic Experiments.

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7. Notes on Specific Experiments and Lab Reports

Expt 1. and 2. Vanillin. Depending on the semester, we will either complete only the reduction, or both the reduction and oxidation. If both are done in one lab period, students will work in teams of two, with one student completing the oxidation and the other the reduction. You will assist each other and learn as much about each other's experiment as possible, since you will be expected to know the procedures and outcomes for both experiments for the lab exams. Product will be characterized by both melting point and solid state IR spectrum.

Expt 3. Friedel Crafts Reaction / Aromatic Substitution. Depending on the experiment performed, the product will be characterized by both melting point and IR spectrum (for a solid) or by GC/MS (for a liquid).

Expt 4. The Grignard Reagent. Your pre-laboratory lecture and quiz (if any) will take place during the week prior to the experiment, so be prepared. The week of the experiment you will begin at the beginning of the lab period; if you are well-prepared, you will have purified but wet product at the end of the day. The following week your product will be dry and can be characterized by melting point and IR. You will have time to take the melting point and IR during experiment 5 if you run into problems (note the extra time for the report). Extra time has been allotted for the report because CHEM 331 may also be using the IRs during this period.

Expt 5.Synthesis of an Amide, Fluorescence and Triboluminescence. This will give you a chance to learn about an important spectroscopic method now used to selectively label biological samples. You will make acetylanthranilic acid which is both fluorescent and triboluminescent and will compare its activity with wintergreen candy, sugar, and other compounds and materials. Product will be characterized by both melting point and IR spectrum.

Expt 6. Lidocaine. This two-step synthesis illustrates the kind of project organic chemists in drug companies might do. It involves reactions of two different amines as nucleophiles, one adding to a carbonyl group (nucleophilic acyl substitution) and the other substituting at a saturated carbon (nucleophilic substitution, S_N2). Product(s) will be characterized by both melting point and IR spectrum.

Expt. 7. Oxidation of Methoxybenzyl Alcohol, Thin Layer Chromatography. This experiment is new and involves interesting techniques. The reaction itself occurs while the two reactants are in different phases, a technique being used commonly to reduce the need for volatile solvents. The reaction's progress will be monitored by thin layer chromatography. This simple (and oldest) version of chromatography is the basis not just of GC and LC, but of electrophoresis and the "gels" used in DNA "fingerprinting".

Expt 8. Identification of an Unknown Compound. You will be given a solid and its MS and NMR spectra. You will obtain the melting point, IR spectrum and any chemical or solubility data yourself. A description of the solubility tests will be provided in a separate handout. Your report format this time will be very flexible. Rather than an abstract, write an essay / report in your own words describing what you think your unknown is and why. Your report should include comparisons with known compounds (see the References and your lecture text as sources of spectral data). Extra time has been allotted for the report because CHEM 331 may also be using the IRs during this period.

Laboratory Exams. The first laboratory exam will concentrate on structure determination, especially spectroscopic techniques and their basis. The second laboratory exam will concentrate on the techniques you learned and the specific reactions you did during the semester.

Inactive experiment Rum: Isobutyl Propionate. This is not a IUPAC name -- what is the structure of the compound? Your only liquid experiment will use the Hickman still for a simple (one plate) distillation. Extra time for the report because CHEM 331 may also be using the IR during this period.

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5. References

These additional sources may be of use to you and may be found in the library (reference, faculty reserve room or stacks), the Chemistry Tutoring Center or in the laboratory itself.


GENERAL LABORATORY TECHNIQUES, CHEMICAL TESTS AND DATA

1. The Organic Chem Lab Survival Manual; A Student's Guide to Techniques, 4th ed., J. W. Zubrick, John Wiley and Sons, NY 1997, 2001. This book manages to be entertaining while explaining the basics of organic lab techniques. Excellent instructions for laboratory notebook .
2. 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
3. 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.
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 in Cook library.

1. Web sites with spectroscopic information, problems, etc.
2. 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!!
3. "NMR Tutor" is more like a set of slides from a lecture class, but explains basics well. Different author from irtutor.
4. 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
5. 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.
6. Introduction to Spectroscopy, D. L. Pavia, G. M. Lampman and G. S. Kriz, Jr., W. G. Saunders Co., Philadelphia 1979. The second best.
7. 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.
8. The Spectrum in Chemistry, J. E. Crooks, Academic Press, London 1978.
9. 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.
10. The Aldrich Library of Infrared Spectra, C. J. Pouchert, Aldrich Chemical Co., Milwaukee 1970. Lots of spectral data for comparison.
11. 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.
12. Merck IR Atlas (FTIR), VCH Publishers Inc., NY 1987.
SAFETY
1. Towson University's SAFETY AND LABORATORY RULES for ORGANIC CHEMISTRY LABORATORIES and STANDARD OPERATING PROCEDURES IN THE ORGANIC CHEMISTRY LABORATORY
2. 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, in alphabetical order by IUPAC name (usually):
• World Wide Web. Several sites I have found to be useful (there are probably others):
• What is an MSDS? http://www.chemweek.com/genium/msds/msdsint.html
• Fisher Chemical http://www.Fisher1.com; select Catalog, Chemical, then an alphabetical range or type in the (IUPAC) name of the compound you wish to search for.
• Enviro-Net http://www.enviro-net.com/technical/msds
• University of Washington, which has connections to other sites, at http://www.hpcc.astro.washington.edu/scied/chem/chemsafety.html
• For links to these and other sites on safety, some with MSDS's, go to the Organic Web Sites links.
3. 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.
4. 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.
5. 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.
6. Aldrich Catalog/Handbook of Fine Chemicals, Aldrich Chemical Co. Basic information and references on the compounds they sell - which is lots.
7. 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.
8. Registry of Toxic Effects of Chemical Substances, NIOSH, Govt. Printing Office, Washington, 198O. The official blurb.
9. Dangerous Properties of Industrial Materials, Sax, N. I., Reinhold, New York, 1984 (6th edition).
10. Handbook of Toxic and Hazardous Chemicals and Carcinogens, Sittig, M., Noyes Publications, Park Ridge, NJ, 1985.
11. 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.
12. Hazards in the Chemical Laboratory, Bretherick, L., The Royal Society of Chemistry, 1986 (4th edition).
13. Hazardous & Toxic Materials: Safe Handling and Disposal, Fawcett H., John Wiley & Sons, New York, 1984.
14. Toxic and Hazardous Industrial Chemicals Safety Manual, International Technical Information Institute, Lab Safety Supply Corp., Tokyo, 1978.
15. Guide for Safety in the Chemical Laboratory, Manufacturing Chemists Association, Van Nostrand & Reinhold, 1954.
16. Safety in the Chemical Laboratory, Steere, N., Division of Chemical Education, American Chemical Society.
17. Handbook of Laboratory Safety, Steere, N., Chemical Rubber Co., (CRC Press), Cleveland, 1967.
18. Prudent Practices for Disposal of Chemicals from Laboratories, National Academy Press, Washington, DC, 1983.
19. Prudent Practices for Handling Hazardous Chemicals in the Laboratory, National Academy Press, Washington, DC, 1981.
20. Safety in Working with Chemicals, Green, McMillan, New York, 1978.
21. Encyclopaedia of Chemistry, Hawley, Van Nostrand Reinhold, New York, 1982.
22. Kirk-Othmer Encyclopaedia of Chemical Technology, 2nd ed. (3rd if avail) Wiley-Interscience, New York, 1972.
23. First Aid Manual for Chemical Accidents, Lefevre, Dowden Hutchinson & Ross, Stroudsburg, 1980.
24. Fire Protection Guide on Hazardous Materials, National Fire Protection Association, Boston, 1975.
25. Hazardous Chemical Data Book, Weiss, Noyes Data Corp., Park Ridge, 1980.
26. Chemistry of Hazardous Materials, Meyer, Prentice-Hall, Englewood Cliffs NJ, 1977.3
27. Safe Storage of Laboratory Chemicals, Pipitone, John Wiley and Sons, NY 1984.3