LabNotes

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ORGANIC CHEMISTRY LAB NOTES
Revised 01.08.2010
INTRODUCTION
This is a laboratory course designed to develop your skills in dealing with experimental problems. A
good experimentalist must have several important qualifications: the ability to pay strict attention to
detail, to reason scientifically, and to master new techniques and manipulate equipment.
Laboratory work is not a jumble of unrelated operations; there must be a good reason for
everything that you do. IF YOU DO NOT KNOW WHAT YOU ARE DOING AND WHY YOU ARE
DOING IT, YOU DO NOT BELONG IN A LABORATORY!
I. LAB NOTEBOOKS
An accurate record of your experimental procedure, results, observations, and conclusions is an
indispensable part of scientific work. Human memory is faulty and unreliable enough that a written
record of results is necessary for future reference. Your notebook should be written so that it is
intelligible to anyone conversant with the subject. See your instructor if you have any questions
about the desired notebook format.
Notebooks must be hardbound and written in permanent ink. We require a bound lab notebook by
Hayden-McNeill, Inc. (ISBN #1-930882-74-2, available at the MTU bookstore) with duplicate pages.
This notebook should have sufficient pages to last through both organic lab courses (2411 and
2421). NOTE: You must use a ball point or other hard-tip pen and write firmly for legible duplicate
pages. The duplicate, carbon copy pages are to be turned in to your instructor each week for
grading.
A. Preliminary Notebook Entries (10pts)
Preparation is required before coming into the laboratory. This will include reading the experiment
and techniques involved, and making some preliminary entries into your notebook. Be sure to read
both Dr. Logue’s lab notes for the experiment as well as the readings assigned from Zubrick before
beginning your preliminary notebook. Preparation for a lab, which includes reading and writing the
preliminary notebook, should take two hours or more. You will find the experiments much easier
and capable of being completed much faster if you are thoroughly acquainted with the experiments
beforehand.
Preliminary notebooks are due before the experiment begins! If your preliminary notebook is not
complete, then you will be asked to leave and finish it before beginning the experiment. An
unprepared student is a safety hazard to other students. Moreover, the unprepared student will
have no chance of finishing the experiment in the time we allow.
The preliminary notebook entries will vary with the type of experiment, but will generally include:
1. A Title
Every experiment must have a title. The title should provide enough of an explanation as
to what was done in the experiment while remaining concise. A title which is over
simplified can be misleading. i.e. “Making Trimyristin” Did you synthesize it from scratch,
isolate it from something, or simply draw a picture of it? A more complete, yet concise title
would be, “Isolation of Trimyristin from Nutmeg”
2. A Reference
Reference the experiment, the techniques, and any handbooks (or web sites) used in the
preparation for the experiment. Please note that page numbers must be included. If one
is referencing a website, then be sure to include title of the webpage and the date the page
was accessed. In general, the ACS format for citations should be used.
3. An Introduction
Keep the introduction brief. Introduce the experiment using only a sentence or two in your
own words. A good introduction should state what you are going to do and how you will
verify that you have done it. Theory and procedure belong somewhere else!
4. The Main Reaction
Include a balanced equation for the main chemical reaction involved in the
experiment. When applicable, it is also helpful to list any potential side reactions that may
occur. The main reaction should not contain any mechanisms.
Note that this entry is appropriate only when the experiment involves a chemical reaction
(i.e., a synthesis). Most of the early CH2411 experiments involve techniques rather than
syntheses.
5. Table of Reagents And Products
Include the following information for all chemicals (every chemical used or synthesized in
the experiment):
a) chemical formula and/or structure
b) amounts to be used in the experiment (weight in grams, volume in milliliters, etc.).
Moles used should be entered as a separate column.
c) important physical constants
i) Include molecular weight and moles for the reactants and products of the main
chemical reaction when applicable.
ii) Include only physical constants which are pertinent to the experiment (i.e. melting
point, boiling point, density, etc.).
d) waste disposal
See solvent table for a good example of this portion of the preliminary notebook as well as
a valuable resource of important physical constants of some common organic solvents.
Be Careful: By all reagents, we mean all. This includes solvents, acid, bases, etc. Too
many times students are found trying to evaporate a solvent from their flask and they have
no idea what temperature to set the hot water bath. Had they been aptly prepared and
known the boiling point for the solvent, they would be spending their time more wisely than
being perplexed.
Physical constants may also be found in handbooks such as:
a) CRC Handbook of Chemistry and Physics, CRC Press, Inc. Boca Raton, Florida.
[Call #QD65.C5, Location: Reference stacks on main floor or Circulating collection on
2nd floor of campus library]
b) Lange’s Handbook of Chemistry, McGraw-Hill Book Company, New York, New York.
[Call #QD65.Lzh, Location: Circulating Collection, 2nd floor of campus library]
c) The Merck Index, Merck & Co., Inc., Rahway, New Jersey.
[Call #RS51.M4..., Reference stacks of main floor or Circulating collection on 2nd floor
of campus library]
d) Aldrich Catalog Handbook of Fine Chemicals, Aldrich Chemical Co., Inc., Milwaukee,
Wisconsin.
Or web sites such as:
a) http://www.emolecules.com/
b) http://www.jtbaker.com/asp/Catalog.asp
c) http://www.chemexper.com/
6. Theoretical Calculation
Any good calculation in a notebook will begin with a good sample calculation. This means
writing out your calculation as an equation of just variables. Then write a second equation
in which the variables have been replaced with the values you will use. Be sure to include
the units in the equation and in the final answer. Once you arrive at the final answer, put a
box around it so that it is easy for a reader to find. Ask your instructor for more
information.
A good calculation for yield will save you time later in the experiment.
7. An Outline of Procedure
Think about the most important steps of the experiment and then condense the procedure.
Put these few steps in some type of outline form or flow chart. Do not include details in the
outline and remember that reagent amounts belong in the reagent table. If you find it
helpful to outline the experiment in more detail, do so outside of your notebook! Please
note that you are not allowed to bring the online notes for an experiment to the lab. There
is a point deduction associated with bringing the notes to lab.
B. Experimental Section (40PTS)
The experimental section of the notebook is due in lab on completion of the experiment. During the
course of the experiment, record all data, observations (and possible interpretations if necessary),
problems encountered and how you solved them, as well as any chromatograms, spectra, etc. If a
portion of the lab has to be repeated due to experimenter error, then document everything. i.e.
what was the source of the error and everything you did the second time. A good experimental
section should be detailed enough that anyone can look at your work and tell exactly what you
have or have not done correctly. Think of it as a record not only for others but for yourself as well.
Take pride in your ability to be observant and documenting your labor!
Do not copy the procedure from the lab notes or other literature source into your note book
beforehand, but write everything you do or observe as it occurs. Use a passive third person past
tense for writing. Experimental sections can either be delivered in a prose, paragraph form.
Otherwise, a bulleted outline format of what you have done and observed is also viable.
Ask your instructor ahead of time what format they prefer to see from you.
This section should include:
1. the procedure as performed
2. all pertinent data (weights, volumes, mp, bp, etc.)
3. all observations (changes in appearance, temp, etc.)
An Acid Test for a Good Notebook1
If this were someone else’s notebook,
could you duplicate the results exactly?
C. Postlab Exercise (30pts)
After completion of the experiment, you should complete the postlab exercise found at the end of
each experiment. Postlab exercises should be turned-in in the lab. Name and section number are
required on the postlabs. Postlabs without name and/or section number will be penalized with a
loss of 2 points each for name and section number. The format of the postlab exercises may vary
somewhat depending upon the nature of the experiment, but will generally require:
1. results (% yield, % composition, etc.)
2. product purity (melting point, boiling point, or some other indication)
3. postlab questions and/or interpretation of spectra
There will also be a few thought-provoking questions in the postlab exercise for you to
answer. The answers to the questions are not necessarily in the experiment or your text and may
require you to use your "chemical intuition".
II. GRADING
Each typical experiment will be worth 90 points, with the following distribution:
1.


Preparation (20 points)
10pts - Preliminary Notebook
10pts - In-lab Quiz (multiple choice or fill-in the blank, based on theory, procedure,
techniques, etc.)
2. Experimental Section (40 points)
3. Postlab Exercise (30 points)
1. ~15pts - Product*
2. ~15pts - Questions
* Product points will be based on the product having the proper appearance, purity as indicated
by M.P. or B.P. and/or TLC analysis, as well as completeness and neatness of the label. When
appropriate, you will be graded on the % yield. When turning in your product for grading, follow the
label format.
Preparation and attitude will be taken into consideration by the instructor in the assignment of the
instructor evaluation points. Five of the fifteen points will be based on the instructor’s evaluation of
your ability to manage time in the laboratory. To obtain all five of these points, plan to: 1) arrive at
lab on time; 2) use lab time efficiently; 3) finish experiment and clean-up within the time allotted for
the experiment.
In addition, deductions from the instructor evaluation points will be made for safety infractions.
Typical infractions include:
1. tardiness
2. conducting unsafe procedures
3. failure to clean up spills
4. improper disposal of waste
5. failure to return common equipment
6. failure to keep your work area orderly and clean
III. LATE PAPER POLICY
A. Preliminary notebook entries are due at the beginning of the lab on the day you start the
experiment. If not completed in time, you will not be allowed to work in lab. You will have to
complete the prelab and make up lab with some other section in the same week.
B. Experimental Portions of the lab notebook are due at the end of the completed experiment
unless otherwise instructed. You will receive 0 points if not turned in on time. No excuses will be
accepted.
C. Postlab Exercises are due during the next lab period after the completion of the experiments.
Postlab exercises should be turned-in in the lab. Name and section number are required on the
postlabs. Postlabs without name and/or section number will be penalized with a loss of 2 points
each for name and section number. Postlabs turned in late will receive 0 points – this includes
postlab exercises of absent / make-up students! NO EXCUSES!
IV. ABSENCE POLICY
A responsible attitude towards attendance is critical to the efficient operation of this laboratory
course. Much of the same responsibility and courtesy shown to an employer are expected from
students enrolled in this course, including attendance during the weekly scheduled lab time. Please
make note of the following:
1. To make up a lab, you must complete an absence request and obtain permission from the
lab supervisor or faculty advisor.
2. Follow the instructions on the absence request carefully. Your absence request will be
reviewed and, if approved, forwarded to the appropriate lab instructors.
3. If after approval of the absence request you decide to perform the experiment in your own
section, please email lab supervisor. Remember there would be other students whose
request was not approved due to lack of space availability.
IMPORTANT ABSENCE POLICY NOTES



All absences must be made up within one week of the missed lab. To facilitate this, please
complete an absence request form or notify the lab supervisor as soon as you know you
will miss a laboratory!
Postlab exercises must be handed in the lab the week they are due. Postlab turned in late
will be assigned 0 points.
You will find the lab supervisor’s phone number, office number, and e-mail address on the
Organic Lab home page.

Three unexcused absences will result in an F for the course. If you suspect that you will be
absent more than once, it is strongly recommended that you obtain validation of your
absence excuse from a physician, counselor, or clergy.
V. WASTE DISPOSAL
Wastes are divided into two basic categories:
1. Those that can be flushed down the drain (run water while pouring these liquids in the
drain; continue running water for a few minutes afterward:
 aqueous solutions of salts, acids, and bases
 water soluble alcohols and acetone.
2. Those which must be collected and shipped to a disposal site. Chemicals in this category
will be deposited in the special containers provided.
NOTE: There are separate containers for nonhalogenated organic waste and halogenated
organic waste (organic compounds with C-Cl or C-Br bonds), which are more costly to
dispose of.
VI. ACCIDENTS AND/OR INJURIES
Notify your instructor of any accident or injury at once! If medical attention is deemed necessary,
you will be transported to the Portage Medical Clinic (MTU Health Center) or to the Portage View
Hospital. Do not leave the laboratory by yourself!
VII. CHECK-OUT/EARLY CHECK-OUT POLICY/PROCEDURE
You must check out of your drawer by the last scheduled lab in the term you drop the lab (usually
4:00p Thursday, week 14 during Fall and Spring Semesters; Wednesday of last week of the track
during Summer). Complete an absence request. You may pick any time or day during a regularlyscheduled lab session, but do not pick a time which is during the 1st or last hour of the session
(see home page for link to lab schedule).
1. When you arrive in lab, put on your goggles and let the instructor know that you need to
check out of your drawer. Since you completed an absence request form, the instructor
should be expecting you and will have the necessary paperwork ready.
2. Remove everything from your drawer and make sure that everything is clean and present.
A list of drawer equipment and the approximate replacement cost is posted on the lab
bulletin boards. Please place desk equipment on the bench in the approximate order of the
list. Equipment replacements must be purchased from Chemistry Stores (B002)*
3. Tell the instructor when you are ready to be checked out. The instructor will obtain your
original check-in certificate and then check over each piece of listed glassware carefully.
You will be expected to replace any equipment found unsuitable. Make sure the instructor
signs and dates your check-out certificate before you leave. The instructor will then change
the lock on the drawer.
NOTE: NEVER LEAVE YOUR EQUIPMENT UNATTENDED!
Zubrick, James W., The Organic Chem Lab Survival Manual: A Student's Guide to Techniques, 7th Edn.,
John Wiley & Sons, Inc., 2004, p. 21
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