CHEMISTRY 355
Instructor:
G. Lampman
Office Hours:
MWF 10 and Th 9
Laboratory Hours: Tuesday 1-5 and Thursday 1-5 in CB 310
Lectures:
1PM in CB 385. When there is no lecture, go directly to the laboratory in CB 310
E-mail address: lampman@chem.wwu.edu
Lampman Web page, available from the Chemistry Dept website:
http://www.chem.wwu.edu/dept/facstaff/lampman/lamp355.html
Required materials for the lab course:
1) Pavia, Lampman, Kriz, Engel "Introduction to Organic Laboratory Techniques, a Microscale Approach, Third Edition, 1999"
2) Chemistry 355 Prelabs and Post Lab Reports are available from my website
3) Bound lab notebook (see page 4 of syllabus).
4) Lab goggles (approved).
ORGANIC CHEMISTRY LABORATORY
FALL 2005 SCHEDULE
EXPERIMENT
Schedule
CHECK-IN TO LAB AND START EXPERIMENT 51 (solubilities, only)
NMR Demonstration with Charlie Wandler may start on Sept 22 or 27.
Additional demos will occur in subsequent lab periods.
Sept. 22
IDENTIFICATION OF ORGANIC COMPOUNDS (EXP. 51)
After completing tests on the knowns, you will be given a liquid and a solid
unknown. The unknowns are to be identified and characterized by solubility
and chemical tests. The unknown reports are due by the end of the quarter and
you may work on them at any time that you have spare time. You may need to
work on them throughout the quarter. No infrared or NMR spectroscopy
allowed until you receive approval!
Sept. 27
Sept. 29
Oct. 4
Oct 6
You are required to complete a total of eight "paper" unknowns from
SQUALOR. Four of these must be even-numbered and four odd-numbered.
The program is available in CB 280. Turn in to me the names and structures
for each compound that you identify.
Dec. 6 (or
when
completed)
Each Exp is
worth 50
points.
Oct. 18
Nov 29
Friedel-Crafts and Chalcones Experiment (Exp 58 and 35). I will assign
you a compound to synthesize by the Friedel-Crafts acylation reaction and
aldol condensation reaction (chalcone). You will need to do a literature search
in order to find a source of the melting point of your chalcone. Starting about
Oct 11th or earlier, you can use SciFinder Scholar to obtain a literature source
for the melting point. Don’t wait until the last minute to do this search! It
may take you awhile to find the journal that contains the melting point. You
may need to obtain the paper by Interlibrary Loan. We do the actual synthesis
from Nov 3 through Nov 15. This experiment will require an extensive
writeup in journal format.
THREE STEP SYNTHESIS OF A POLYMER: Diels-Alder reaction,
formation of a diester, and ROMP polymerization.
This is a new experiment. I will pass out the procedure in advance. All you
need to do during the first period is to mix the two compounds for the DielsAlder reaction. For the rest of the period, work on your unknowns (Exp 51).
Report
Due Date
Oct. 11
Oct. 13
Oct. 18
Oct. 25
-2-
EXPERIMENT
Schedule
Report
Due Date
PALLADIUM CATALYZED COUPLING OF AN ARYL HALIDE
WITH 1-PENTYNE. This is also a new experiment. It can be done in one
period. Work in pairs for this experiment.
Oct. 20
MIDTERM EXAMINATION. Finish the palladium catalyzed coupling
experiment or work on your unknowns after completing the midterm.
Oct. 25
AN OXIDATION-REDUCTION SCHEME: BORNEOL, CAMPHOR
ISOBORNEOL (EXP. 28)
This experiment uses some "green chemistry," sodium hypochlorite (bleach)
for the oxidation. We use sodium borohydride for the reduction.
Oct. 27
Nov. 1
Nov. 8
FRIEDEL-CRAFTS ACYLATION (EXP. 58)
Read pp. 493-499 and technique sections listed on page 495. We will be using
infrared, proton and carbon nmr spectroscopy for structure proof so you should
read Technique 19 and Appendix 3, 4 and 5. Scale up the reaction by 2 times.
Omit the vacuum distillation procedure and b.p. determination on p. 498.
Nov. 3
Nov. 8
This is the
first step in
the
synthesis of
a chalcone
THE ALDOL CONDENSATION: PREPARATION OF
BENZALACETOPHENONES (CHALCONES) (EXP. 35).
You will take your Friedel-Crafts product (Exp 58) and convert it to the
chalcone using the procedure given in Exp 35. You will need the melting
point that you found in the chemical literature using SciFinder to see if your
can duplicate the literature value. You will need to determine the infrared
spectrum and proton and carbon NMR spectra.
Nov. 10
Nov. 15
The two
step
synthesis
will be
written up
in Journal
style
GRIGNARD REACTION: Preparation of Naproxen ("Aleve")
Work in pairs for this experiment. Read pp. 292-297 and the appropriate
techniques listed on page 294. I will give you a procedure for the synthesis of
naproxen (handout). In addition, I will give you a procedure for the resolution
and isolation of (S) naproxen. We will determine the purity of (S) naproxen
by chiral HPLC.
Nov. 17
Nov. 22
Nov. 29
Dec. 1
CHECK-OUT OF LABORATORY AND CLEAN UP
FINAL EXAMINATION
Dec. 1
Tues Dec 6,
1-3pm
Oct. 27
-3A. Safety Quiz
All organic chemistry lab students must take and pass a safety quiz even if you have taken the test in
previous laboratory courses. You may study for this quiz by looking at the material posted on the web at:
http://atom.chem.wwu.edu/dept/osafety/index.htm You may also study some of this material in the
Textbook on pages 4 to 20. When you are ready to take the quiz, go to the following website. You have 30
minutes to take the test:
http://argon.chem.wwu.edu/safetyQ/OCQLink.htm
The quiz consists of 25 multiple choice questions. In order to pass the safety quiz during the first time it is
administered, you must obtain a minimum passing score of 80% (20/25). In order to pass the safety quiz
during the second time it is administered, you must obtain a minimum passing score of 84% (21/25). In
order to pass the safety quiz during the third time it is administered, you must obtain a minimum passing
score of 88% (22/25). Failure of the quiz three times means that you may not register for the class.
Here is the schedule of each safety quiz:
1st Try: Wednesday, Sept. 21, 8 AM to Friday, Sept. 23, 5 PM (80% is passing)
2nd Try: Friday, Sept. 23, 5:30 PM to Tuesday, Sept. 27, 5 PM (84% is passing)
3rd Try: Tuesday, Sept. 27, 5:30 PM to Thursday, Sept. 29, 10 AM (88% is passing)
B. Some things to remember in the organic chemistry laboratory
1. Wear safety glasses at all times. If you don't have a pair already, please purchase them from the
bookstore. The safety glasses must completely cover the eyes, with no gaps.
2. No open flames are allowed in the laboratory except as noted by the instructor. You can use a hot plate
or aluminum blocks or a hot water bath for heating liquids.
3. Note positions of eye wash fountains, safety showers, and fire extinguishers.
4. Please don't bring food or drinks into the lab.
5. Organic solvents must be kept in the solvent hood. Handle solvents with care and avoid contact with
skin (use gloves, if necessary). Don't breathe solvent fumes. Always evaporate solvents in the hood!
Most solvents are toxic!
6. Proper disposal of organic solvents: We have waste containers in a hood for proper disposal of organic
compounds. Aqueous solvents should be poured into the appropriate waste container, as well. If in
doubt as to where to put the stuff, please ask.
7. Dispensing reagents: You should always take a spatula with you when you go to the balance to aid in
transfer of solids. A dropper and Pasteur Pipet are useful for liquids. Be sure to clean up any spills on
the balance pan. Read pages 43-45 and pages 512-519 for help in transferring and measuring liquids.
8. Report all accidents to your instructor, immediately!
9. Students are responsible for their own medical coverage in case of injury.
-410. Clean up your laboratory bench and hood before leaving the lab. If you have used a hood or balance,
be sure that it is clean, too. If we do well in cleaning during the quarter our cleanup duties on Dec. 2nd
will be minimized! Clean up any spills when they occur!
11. You must do your laboratory work during our laboratory periods. Attendance is required unless
permission has been obtained in advance from the instructor. No makeup periods have been scheduled!
Good lab preparation, in advance of the lab, improves safety!
C. Laboratory Fee
A laboratory fee of $42.16 has been included as part of the fees that each student must pay as part of tuition
and fees. This fee covers normal and minimal breakage as well as costs associated with chemicals and
supplies needed in this course. The money also helps in costs associated with replacing expensive
instrumentation required with doing modern chemistry. Students who break expensive glassware in excess
of the normal amount will be required to pay for broken items. Please be careful! You will be required to
pay for any missing equipment at the end of the quarter at the check-out time!
D. Check-in to laboratory
On Sept 22nd you will be given a check-in list, including a combination number for your lock. Carefully
check your equipment against the list (Text: pp. 33-36). If you are missing items, get them from the
stockroom attendant. After Sept 22nd, you must pay for anything that is lost. Make sure that you
remember to put the clamps away at the end of the period! Be sure to write down your combination
number and lock your locker before leaving the laboratory. Many students aren't too careful on this score!
You will not need to pay for breakage as long as it is minimal. Departmental policy requires that student's
checkout of the laboratory at the end of the quarter (including mid-term withdrawals). You will have to pay
fine if you fail to property check out of the laboratory by the end of the quarter.
E. Prelab reports. Complete the prelab report and turn it before the end of the period. There is no prelab
report for Experiment 51. The others are assigned a value of 5 points.
F. Laboratory Records and Reports (Pages 20-27 of text)
A bound laboratory notebook is required for taking notes, writing procedures and recording data. The
bookstore has several types of notebooks. Pick one that is lined. If the pages aren't numbered, you should
number them yourself in ink. Allow the first several pages for a table of contents. Allow an adequate
number of pages for the experiment, so that one doesn't have to skip ahead in the notebook. All notebook
entries must be made in ink, and all data recorded directly into the notebook at the time of observation. In
preparing for an experiment, you must outline the laboratory procedure in your notebook. In addition, any
calculations that are required will be done in your notebook prior to starting the experiment. A
recommended format is shown in "Advanced Preparation and Laboratory Records" (pp 20-27). I will
inspect your laboratory notebook on the day you start the lab experiment. A brief procedure should be
included, along with any necessary calculations asked for in the experimental procedure. I will come to your
desk to look at the write up during the laboratory period. Your pre-lab report should be turned in by the end
of the period. The pre-lab and post-lab reports can be downloaded and printed from my website for
Chemistry 355. Transfer the appropriate information from your laboratory notebook onto the
-5sheets. These reports should be submitted by the due date indicated on the schedule. The report sheets
include spaces for answers to the assigned questions. The reports must be legible and you must follow
acceptable standards of English, including correct spelling. If necessary, download a clean copy of the
report and start again!
G. Turning in samples of products (Page 27 of text)
Submit samples in a properly labeled vial with the report sheet on the laboratory due dates. Do not discard
your samples unless instructed to do so! See page 27 of the text for label format.
H. Laboratory tests (two @100 point each)
Two tests will be given during the quarter. The first one will cover Experiment 51 only. The second test
will cover the remainder of the experiments.
I.
TEST 1:
Tuesday, Oct 25, in CB 385
TEST 2:
Tuesday, Dec 6, 1-3PM in CB 385
Grade in course
The final grade in this course is based on the quality of the laboratory reports: 30 points for four
experiments (25 for the post lab report and 5 points for the prelab report). The two reports on your liquid
and solid are worth 50 pts each. The journal writeup will be assigned 80 points.
300 pts laboratory
200 pts examinations