Syllabus and Laboratory Schedule                     Spring, 2001 

Instructor: J. Almy, office S 253; phone 667-3551; secretary 667-3468; e-mail: almy@chem.csustan.edu

Text: "Microscale Techniques for the Organic Laboratory" by Mayo, et. al.

Each experiment in the schedule below is available on the class directory from the Chemistry web page. Download these experiments well before the lab to avoid complications with printers, etc. and to prepare adequately for the quiz: http://wwwchem.csustan.edu/chem3012/

Grading: Option 3 - exclusively A, B, C, D, F based on:

Quizzes (20%) are given promptly at the beginning of each laboratory except the first one. They will be based on all sections before the Procedure part of each experiment. Note: the quiz for the second laboratory will cover the 1st and 2nd labs.

Laboratory Notebook (80%) will be issued at the first lab. All entries in ink. Leave the first 2 pages for a table of contents. Mayo et al., p 47-48 gives a good example. Use both sides of each page. Leave 2 pages for for notes taken and one blank page between experiments. Do not worry about how messy the book may look - it is a record of your work. No erasures or white out; line out what you didn't mean and insert what you do. No taking data on separate slips of paper for later insertion; record all data directly even if it is first entered into the ‘notes' page (which is not graded). Each lab report should have a:

Purpose. This is prepared before the lab and should very brief using one or two sentences. Pre-lab preparation also includes insertion of any data requested in the text before the Procedure section. Here and elsewhere, any question requiring a short answer should be answered where the question appears in the text.

Procedure. If you ever repeat the experiment or you ever need to carry out some related work, your notebook should be a complete guide. The procedure from the file should be cut and attached to pages in the notebook. Leave ample spaces where you will need to respond to a question or make a calculation, a drawing that explains a technique setup, etc. Any changes that were made must be noted at the relevant point in the procedures. Write answers to short questions between lines of the text, or in margins as they appear in the laboratory assignment. Number your answers to any numbered questions.

Data.. The data pages are also set up before the lab and filled in during the lab or can be copied from ‘notes’ pages. It should follow a logical line reasoning; for example, "mass of empty beaker…" then "mass of beaker with.. ." then "mass of …" should be clearly listed.
    Usually the data can be organized into tables. The kinds of tables expected follow, with a more detailed example of each in the "Common Practices…" file which is accessed from the Chem 3102 index webpage.

1. A "reaction table" for experiments in which an organic compound is converted (through one or more steps) to a product which is weighed and analyzed. From this table the theoretical yield of a reaction is normally calculated.
2. A "test table" and a "table of candidates" for experiments involving the identification of an unknown compound
3. Other tables will be necessary to organize data from experiments carried out by the entire class; details will be given.
4. Spectra and gas chromatograms are to be attached to notebook pages and fully annotated. Instructions on their treatment are found in the "Common Practices.." file.

Observations. Was heat evolved? A color change? A smell?

Discussion. This section is for evaluating (not re-reporting) the data and observations. Graphs are titled and set up to fill up at least half a notebook page; axes are clearly marked with evenly spaced increments. What comparisons can be made from the data? Save space for comparison of your data/findings with those of other students. If you were to repeat this experiment, what would you watch out for, and what would you change?

Conclusions. Give one or two sentences which respond to the initial purpose of the laboratory. Avoid repeating material; instead provide a brief but general statement that encompasses the discussion, if it is appropriate.

Some goals for the course. You will:

1. Become familiar with some basic techniques of experimental organic chemistry. Among these are
    a) handling of solids and liquids, particularly at the microscale level commonly used in chemistry and biology professions
    b) purification of compounds by distillation, gas chromatography, extraction and recrystallization
    c) analysis of compounds by gas chromatography, melting and boiling point determination and spectroscopy
2. Learn to document your findings in a form that will be both standard practice for scientists and a practical reference for future work
3. Become self sufficient and self reliant in the laboratory. For example you will be encouraged to interpret your own findings and evaluate often conflicting data to make decisions on your own.
4. Adapt to changes in the procedures. Most laboratory scientists innovate by substituting or altering a previously set plan to fit changing circumstances.
5. Cooperate with others to develop combined sets of data. Often the parameters of your own experiment will be slightly different from the others; you will compare your data with those of the rest of the class. Analysis of shared data will enable you to note trends and/or evaluate methods. The ability to identify patterns from data sets and then to make inferences from these patterns are important skills for scientists.
6. Learn to use laboratory time to its best advantage by preparing ahead of time as much as possible. If other students have lined up for some task such as weighing out a reagent, you will learn to work on a parallel task and return to the line when it is shorter. Another skill you will learn is "multitasking," that is carrying out one experiment while another is undergoing a reaction for an extended time. Knowing when to be "quick and dirty" and when to be careful can save lots of time and is a very valuable skill in any professional scientific setting. When a procedure calls for "1/2 mL of methanol" for example, this doesn’t mean "0.500 ml" but an approximate amount that can be delivered rapidly from a Pasteur pipette. Another time-saver is in preparing containers: if a beaker is to be cleaned in order to contain 6 M HCl, for example, it need not be dried beforehand.

Students occasionally approach organic chemistry lab with the implicit expectation that they can be passive learners by just following directions. They expect that the instructor or others in the class will a) tell them exactly what to do; b) know exactly what "went wrong" and give specific instructions to remedy the situation in order to finish with the others; and/or c) grant a "that’s all right" and allow the student full credit anyway even if there are no results.
    This is not the case for organic chemistry laboratory. After a full year of general chemistry, students are expected to be far more on their own. Careful study of the procedures, even if they are altered, will reveal not only what to do by why it is done. In preparing, the student needs to relate each action to be carried out with the actual change the organic molecules are undergoing. This kind of preparation greatly reduces the "went wrong" problem. Experimental work implies that no outcome is certain, however; some students will wind up with less satisfactory results than others. This can be remedied by repeating the experiment; there is no penalty for repetition and sufficient time is available in these cases during the lab, particularly since repeated work takes far less time.
    Laboratory time is limited. Make ready for it ahead of time by inserting the Purpose and the Procedure in your notebook. You are responsible the Preparation section before each lab. If you anticipate making a decision on an unknown, for example, have all the information from the library before starting the lab. Spend quality time in the lab. For unknown compounds you should repeat tests, for example, or boiling points, run tests on known substances, etc. to if you need to resolve impasses. Leave the time outside the lab to analyze the data.

Note: Unless otherwise written in the procedures, students will carry out experiments individually.

Note: For accurate weighings (to 1 mg) use only the balances in the balance room on the South wall or the West wall.

In the schedule below, the dates mm/dd are given for each section for each laboratory assignment.

Reference materials:

Text, frequently "Mayo et al." in the procedures: Mayo, D.W., Pike, R.M., Butcher, S.S. and Trumper, P.K. Microscale Techniques for the Organic Laboratory; Wiley: New York, 1991

Text for the Lecture, frequently "McM" in the procedures: McMurry, J. Organic Chemistry, 5th ed., Brooks/Cole Publishing Company, Pacific Grove, CA. 1999.

The "Handbook" refers to any of the recent editions of: Weast, R.D. Handbook of Chemistry and Physics; The Chemical Rubber Co.: Cleveland, 1960-present.

The "Aldrich IR Library" refers to any edition of: Pouchert, C.J. The Aldrich Library of Infrared Spectra; Aldrich Chemical Co.: Milwaukee, 1970-present.

Directory for Organic Chemistry Laboratory I: http://science.csustan.edu/almy/3012/