CHEMISTRY 204: ORGANIC CHEMISTRY LAB
FALL 2001
Objectives The main objective of the laboratory component of this course is to enhance your
understanding of the facts and theories of organic chemistry by having you consider them in the
context of lab—where chemistry really happens. To this end, the labs will usually parallel what is
being discussed in lecture. A further objective is to introduce you to some of the common techniques
of experimental organic chemistry.
Rationale There is no substitute for hands-on experience. Most people learn best by doing. Lab is
where organic chemistry should come to life!
Texts The required text for this course is “Organic Laboratory Techniques: A Microscale Approach”
by Pavia, Lampman, Kriz, and Engel, THIRD EDITION, hereafter referred to as Pavia. In addition to
thoroughly reading the relevant material in your lab text, you are expected to use your lecture
text and notes to further your understanding of the theory behind EACH of the labs.
The Lab Notebook
You are required to keep a written record of ALL of your experimental work, data, observations,
results, and analysis of your results. This MUST be kept in a sewn BOUND notebook. In NO case is
a loose-leaf notebook acceptable. Pages should be numbered. Pages should not be torn out. The
first few pages should be used as an index. Lab notebooks should be written in ink and be LEGIBLE.
PICTURES of the apparati used are often HELPFUL! The format for the lab notebook will vary
somewhat depending on the type of lab we are doing. This will be discussed more in lab. Notebooks
will be collected and GRADED periodically during the semester. Dates for this will be announced in
lab or lecture. ALL DATA THAT IS NOT WRITTEN IN THE NOTEBOOK (like IR or NMR spectra)
MUST BE SECURED BY TAPING OR STAPLING IN THE NOTEBOOK. Notebooks submitted with
loose papers will be assigned a grade of ZERO and will be returned without further review.
PRE-LABS MUST BE COMPLETED in the notebook BEFORE THE LAB PERIOD BEGINS! The
format will vary somewhat depending on the nature of the lab. Students who do not have pre-labs
completed will be allowed to take the lab quiz but will dismissed from lab and will receive a ZERO for
that lab grade. There will be no exceptions to this. A complete mechanism for the main reaction
should be included in the pre-lab. This means the CURVED ARROW FORMALISM which shows the
movement of electrons should be used. It also should include a very brief statement of the specific
value of the experiment as well as a list of ALL chemicals used and the purpose of each one.
TABLES are a VERY GOOD thing! Please pay attention to keeping a TABLE of REAGENTS for both
those reagents used in the reaction and those which qualify as auxiliary reagents. If you have any
doubt about which is which, ask yourself if you can do the reaction (not necessarily the work-up)
without the reagent in question. If you don’t need the reagent to do the desired reaction, it’s probably
an auxiliary reagent. If it goes into the reaction pot, it is NOT auxiliary. Also note that your data and
results should be SUMMARIZED in a TABLE. Calculations are also good things to put in TABLES.
Remember: TABLES are exceedingly GOOD THINGS!! Please use them.
PROCEDURE NOTES should be outlined before lab. Flow charts are very useful for this! Changes in
procedures should be noted in the notebook. You MUST keep a running record of your experimental
work AS YOU DO IT.
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Lab write-ups are to be completed (in your notebook) before the beginning of the pre-lab lecture
ONE WEEK after the experiment is SCHEDULED to be completed. Notebooks may be collected
for a grade without prior notice. Please plan your work habits accordingly.
The lab write-up should include the overall reaction being done, the weight and percent yield of
products (SHOW THE CALCULATIONS!! The ones that reflect YOUR actual experiment, NOT just
your prep work!!!) as well as their identifying properties (compared to the literature value which you
must reference). You should include a summary of your results IN APPROPRIATE TABLES,
suggestions for improvement or extension of the experiment, and any startling revelations. Rehash of
the experiment is an unnecessary waste of time and paper. You should keep a copy of all
spectroscopic data (IR, NMR, GC, etc.) SECURELY FASTENED in your lab notebook. Interpretation
of this data (SUMMARIZED IN A TABLE) will be an important part of the lab notebook grade.
Other Things to Note Labs that are missed without prior notice may not be made up except under
the most unusual of circumstances. A ZERO will be given for labs that are missed without prior
notification. Most lab sections will run close to full capacity. You should not assume that you will
be able to go to another lab to make up a missed lab.
HOW IS LAB RUN???
Each lab will begin PROMPTLY at 1:00pm in Science 123. This meeting will begin with a BRIEF
open lab notebook QUIZ followed by a BRIEF pre-lab lecture. Each week, there will be at least one
question specifically relevant to LECTURE material included on the LAB quiz. Missed quizzes may
not be made up. The last ten minutes (or so) of lab will be used as a WRAP-UP, REVIEW, and
PREVIEW. The lab of the week will be completed and reviewed. Techniques and chemistry of the
lab will be discussed. In addition, this will be a time for previewing what the following week’s lab will
be. ATTENDANCE IS REQUIRED.
Please note that it will require diligent PREPARATION IN ADVANCE of your scheduled lab meeting
for you to complete the experiments in the allotted time. If you are familiar with the experimental set
up and are efficient in your work, you should be able to complete the experiments on time.
LAB CHECK-OUT You will be required to CHECK OUT of lab each week. This will involve
convincing your instructor or Teaching Assistant (TA) that you have cleaned up your work area,
properly disposed of wastes, and THOROUGHLY washed your glassware. Only after your glassware
and work area have been checked by your TA or instructor should you return your CLEAN glassware
and supplies to the designated locations. Failure to follow this procedure will result in a penalty to that
lab grade.
SAFETY IS A PRIORITY!!!
Safety Glasses Glasses with side shields or well-fitting goggles MUST be worn AT ALL TIMES in the
laboratory, stockroom, instrument rooms, and any other time or place that you are near by or handling
chemicals INCLUDING the hallways!! Lab glasses, side shields, and goggles may be purchased in
the bookstore. CONTACT LENSES ARE NOT PERMITTED TO BE WORN IN THE LAB. Volatile
chemicals may be trapped under contacts. This can prevent normal eye irrigation and depending on
the chemicals, blindness can result. In extreme cases, it also can lead to the need for surgical
removal of contact lenses. CONTACT LENSES ARE A SERIOUS SAFETY RISK IN THE
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LABORATORY. THEY SHOULD BE REMOVED BEFORE YOU COME FOR THE PRE-LAB
LECTURE!! If you have a medical need to wear contacts, you MUST discuss this with your instructor
PRIOR TO the first experiment.
Your instructor will determine what is appropriate eye protection for you. You are expected to comply
at all times with the good advice or your instructors and TAs.
It should be clearly understood that violations of these and other safety
guidelines will result in students being dismissed from lab and the grade
being penalized.
Students dismissed from lab for lack of a completed pre-lab or safety violation will not be permitted to
make the lab up at another time.
Grading Policy The lab grade will make up 25% of your overall grade for Chemistry 204. The sum of
the lab notebook grades and lab reports will contribute to 40% of your lab grade. The weekly lab
quizzes will contribute 40%, and your technique grade will contribute to 20% of your final lab grade.
Your technique grade will reflect your diligent preparation (or lack thereof), understanding of the lab,
efficiency in carrying out the experiment, etc.
The Schedule of Events
The lab schedule of events (experiments, types, etc.) is on a separate page for your convenience.
HINT: Attaching a copy of the schedule to the inside cover of your
lab notebook is an exceedingly GOOD IDEA!
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LAB WEEK OF
EXPERIMENT
#1 9/3 - 9/6
Functional groups, Spectroscopic
& Identification Techniques (IR), %
yield, density, etc.), Stoichiometry
review
Read Wade Chapter 12
Pavia Appendix 3 (
begins on p A14)
#2 9/10 - 9/13
NMR
Wade Chapter 13
Pavia, Appendix 4
(begins on p A32)
#3 9/17 - 9/20
Macroscale extraction
Handout
#4 9/24 - 9/27
Free radical bromination
Macroscale extraction finish??
Handout
#5 10/1 - 10/4
Stereochemistry
Handout
10/8 – 10/11
NO LABS MEET-FALL BREAK
#6 10/15 - 10/18
Resolution of Enantiomers Week 1
#7 10/22 -10/25
Resolution of Enantiomers Week 2
#8 10/29 – 11/1
Resolution of Enantiomers Week 3
#9
11/5 – 11/8
#10 11/12 – 11/15
11/19 – 11/22
Exp. # 30 p. 285
Alkyl halides
Exp. #18 p.190
Dichlorocarbene
Exp. #26 p. 248
NO LABS MEET-THANKSGIVING
#11 11/26 – 11/29
Dichlorocarbene continued
#12 12/3 – 12/6
Luminol
Exp. #50 p. 422
Read essay p. 419
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