PLU
Organic Chemistry
Laboratory II
(Chem 334) |
A COSY NMR Spectrum
|
Fall 2000 Syllabus for ORGANIC CHEMISTRY LABORATORY II (334)
This Course Accompanies Organic
Chemistry II - Chem 332.
Instructor: C. Fryhle
Office: Rieke Science Center 240
Phone: 253-535-8314
Email: fryhle@rainier.chem.plu.edu
Course Materials:
1) Introduction to Organic Laboratory Techniques - A Microscale
Approach, Pavia et al, Saunders, 3rd ed., 1999
2) Laboratory Notebook, bound quadrilled carbon-less form type.
3) Lab Safety Goggles
Laboratory Schedule
| Week |
Date |
The Experiments |
Exercises |
Points |
|
Sept. 11-15 |
Take Open Lab Safety Tour
Study introductory material on Laboratory Safety, Advance Preparation
and Laboratory Records, and Laboratory Glassware, pp 2-36. Read and
Study (no lab work) Experiment 1 "Introduction to Microscale Laboratory"
pp. 38-49 |
None |
None |
| I |
Sept. 18-22 |
The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride (Exp.
48, p. 406). Take an IR spectrum of your product and attach it to
your report with assignment of major absorption bands.
Essay: "Diels-Alder Reaction and Insecticides", p. 402. |
1, 3, 4 |
40 |
| II |
Sept. 25-29 |
Relative Reactivities of Several Aromatic Compounds (Exp. 39, p. 338).
Take an IR spectrum of your product and attach it to your report with assignment
of major absorption bands. |
1 |
40 |
| III |
Oct. 2-6 |
The Aldol Condensation: Preparation of Benzalacetones
and Benzalacetophenones (Exp. 35,p. 316, omit molecular modeling option).
Take an IR spectrum of your product and attach it to your report with assignment
of major absorption bands. |
1,2,4c,e |
40 |
| IV |
Oct. 9-13 |
Preparation of an alpha,beta-unsaturated Ketone via Michael and Aldol
Condensation Ractions (Exp. 36, p. 320). Use your product from Exp.
35 as the starting material for Exp. 36. Take an IR spectrum of your
product and attach it to your report with assignment of major absorption
bands. |
3 |
40 |
| V |
Oct. 16-20 |
Preparation and Properties of Polymers (Expt. 47A-D, p. 395), and Essay:
"Polymers and Plastics", p. 385. Obtain IR spectra for the polymers
and submit for grading. |
3, 4, 5, 6, 7 |
40 |
| VI |
Oct. 23-25 |
Individual Formal Report
(and Midsemester Break, Oct. 26 and 27)
|
|
|
| VII |
Oct. 30-Nov. 3 |
Individual Formal Report (cont'd)
|
(Due Nov. 3, 5:00 PM)
|
100
|
| VIII |
Nov. 6-10 |
Identification of Organic Unknown I
(Procedures found in Expt. 51, p. 428. See also Techniques in
Part Eight and in the Appendices, as needed) |
Submit Unknown Report Form [Provided at Stockroom] |
40 |
| IX |
Nov. 13-17 |
Identification of Organic Unknown II |
Submit Unknown Report Form |
40 |
| X |
Nov. 20-22 |
Continue work on Unknown II (Thanksgiving Week) |
|
|
| XI |
Nov. 27 - Dec. 1 |
Identification of Organic Unknown III |
Submit Unknown Report Form |
40 |
| XII |
Dec. 4-8 |
Luminol - Chemiluminescence (Exp. 50) and
Essay: "Fireflies and Photochemistry" |
No Exercises |
35 |
| XIII |
December 11-15 |
Lab Final Exam
|
|
40 |
|
December 15 |
Lab Notebooks Collected |
Grade is for notebook check |
20 |
|
|
|
Total Possible |
515
|
Laboratory Safety:
You must complete a Chemistry Department Laboratory Safety Tour before
you can begin work in the Open laboratory. You must also read and sign
the Department's safety policies sheet, titled "Laboratory Safety", and
turn it in at the Stockroom at the end of your safety tour.
-
Be sure to read Pavia, et al, regarding safety information and precautions
that must be taken in the laboratory.
-
Goggles are required at all times in the laboratory.
-
Food and drink are prohibited in the Open Laboratory.
-
Foot apparel must cover your full foot. Open-toe shoes or sandals
are not allowed. If you are not wearing proper footwear you will
not be allowed to work in the Open Lab.
-
Material Safety Data Sheets (MSDS) are explained on pp. 9-11 in Pavia.
MSDSs for the reagents you will use in each week's experiment are available
at the Teaching Station (center) of the Open Lab. MSDSs can also be accessed
on-line via the Department
of Chemistry Home Page. They should be consulted during the preparation
of your prelab report for information about the hazards and properties
of the chemicals you will use. It is also helpful to record the Registry
Numbers in your notebook for the reagents used.
-
Disposable gloves are available at the Stockroom window for a small fee.
In
general, I recommend that you do not use gloves. If you do use gloves,
you must remove them before handling any communal items such as
balances, reagent bottles, pipets, telephones, door knobs, etc., or else
you will contaminate the items you touch and make it unsafe for others
not wearing gloves.
The Lab Notebook:
Your notebook should be a complete and continuously updated diary or journal
for your work in the laboratory. Your notebook is the only place
where notes about your laboratory work should be kept, and it should be
a thorough record of your work. A stranger with approximately
your level of training should be able to read your notebook, repeat your
work without any additional assistance, and obtain results similar to your
own. In research and industrial situations, a laboratory notebook is
a legal document that is signed daily by the author and frequently by a
witness. You should ascribe corresponding importance to your laboratory
notebook.
-
The notebook specified for this course is designed to make carbon-less
copies of your notes. Use your notebook for recording ALL of your
work in the laboratory.
-
Use indelible ink for all notebook entries. Pencil or water soluble inks
are not acceptible.
-
Scraps of paper or notes written on loose paper are not acceptable.
Faculty in the Open Lab have been instructed to confiscate any notes not
written in the specified bound notebook.
-
You may use the back side of your notebook pages (those pages on the left
when the notebook is open) for scratch notes or preliminary ("back of the
envelope" type) calculations, etc. when the need arises. These are notes
for your use that are not part of the report when it is turned in.
-
You are not to re-copy lab notes before turning them in. The notebook
is to be a living diary of the work you did in the lab at as close to the
moment you did it as possible.
-
If your notebook cover does not provide for a Table of Contents, set aside
the first several pages of your notebook to keep a running Table of
Contents. Add an entry to the Table of Contents each time you perform
an experiment, noting the relevant pages.
-
Any errors that are made in the notebook should be crossed out by a single
line. Errors should not be obliterated by erasing, drawing over, or covering
with paper or correcting fluid. It is occasionally the case that what was
considered to be an erroneous entry at one time turns out to be correct
or valuable and is needed at some later date.
-
The prelab portion of your report (specified below) must be complete and
initialed by the Open Lab instructor before you will be allowed to check
equipment out of the stockroom and begin work.
-
The number of points possible for each experiment is listed above in the
Schedule
of Experiments table. The Pre-Lab portion of each report is worth 10
points. The In-Lab notes are worth 15 points. Assigned exercises are worth
5 points. When there is a sample produced by an experiment the sample itself
is worth 5 points and the properly labeled vial is also worth 5 points.
Thus, the maximum possible for most experiments is 40 points. If there
are no exercises and/or there is no sample produced then the total possible
is reduced by the corresponding amount.
Format for Lab Notes:
Your notebook format should be basically that described in Pavia et al.,
pp. 21-27. The Pavia model as well as a few additional required sections
are listed by the headings below. Be sure to begin the notebook with the
Table
of Contents, as specified above.
| Prelab Portion (10 Points) |
Reference (e.g., Pavia et al., Exp. X, pp. YY-ZZ)
Goal or Purpose (brief but descriptive)
Main Reaction [balanced equation(s), including likely side reactions]
(Note
that this section might not be appropriate for non-preparative experiments.
In this case a few brief statement about the work to be done will suffice.)
Table of Relevant Physical Constants or "Reaction Table" Format
- MW, mp or bp, density (for liquids), planned weights and moles, actual
amounts and moles (the amounts actually used are filled in after the experiment
is begun), ratio of moles between reactants (the limiting reagent is used
as the lowest common denominator), and Registry Numbers for organic and
hazardous inorganic reagents.
Separation Scheme (Usually a flow chart - not a written duplicate
of the planned lab procedure copied from the book. - Be concise but
complete.) The goal of this section is to show where actual physical
separations of materials occur (and what the materials are) as you move
through the experiment to obtain a pure, isolated material.
HAZARDS (of the chemicals and/or the procedures) In addition
to the lab manual, you will need to consult the Material Safety Data Sheets
(MSDS's) available on-line (Department
of Chemistry Home Page) and in the Open Lab. Registry Numbers
can also be listed her , if not noted already included in your Reaction
Table.
[All of the above sections must be entered in your notebook
and initialed by the instructor on duty before the Stockroom
will be allowed to issue you your equipment.]
|
| In-lab Portion (15 Points) |
In-lab Notes, Data, and Observations - Written continuously
during the lab period documenting your work in your notebook as
you do the work, not at some later time or date. Your notes should be sufficient
for someone else to duplicate your work, even though your notes may not
necessarily be in perfect prose.
Calculations - Theoretical yield and actual percentage yield.
Conclusions - Brief statement or restatement of key results
and conclusions. Editorial comments such as "I think the experiment went
well.", etc., are not appropriate.
Date of Completion
Attribution of assistance from others (List the names of other people
consulted in the course of your work. See "Academic Policies", below,
for further information.)
Your Signature attesting to the honesty and accuracy of your work.
Reports will not be graded without a signature.
|
Reaction Products
(10 Points for Sample and Vial)
Products requiring further work at a later time should be stored in
a labeled vial and given to the stockroom assistants for storage. Final
products should be labeled as specified on p. 27 of Pavia, et al, with
the addition of the date, tare weight of the container and experiment number,
and turned in to the stockroom with the specification that they are to
be placed in the "To Be Graded" box for the organic lab.
Weekly Reports
The completed lab notes for each experiment, consisting of your work from
the prelab through the completed exercises, are due by 2:00 PM on
the Monday of the week following a given experiment. Place either the original
or carbon-less copy (so long as it is legible) of your lab notes in the
appropriate wooden box in the Open Laboratory.
Notebook Spot Checks
In addition, individual lab notebooks may be subject to an unannounced
on-the-spot grading once during the semester. This evaluation, worth 20
points, will be part of the overall notebook score and will be used to
assess whether the attributes of notebook style specified above are being
incorporated. Notebooks will be collected at the end of the semester.
The Formal Report
The period of October 23-November 3 is set aside for individual
preparation of a formal written laboratory report about one of the previously
conducted experiments (the reports will not be done in groups, as in Chemistry
234). The formal report will be due November 3 at 5:00 p.m.. Some
guidelines for the report are as follows:
-
The formal report may be written about any experiment conducted thus far
during the semester.
-
The formal report is to take the form of a full paper to be submitted for
publication in a journal of the American Chemical Society, e.g. the Journal
of Organic Chemistry or the Journal of the American Chemical Society.
-
The paper should include the following sections:
Affiliation (Course and Institution address)
Expectations for the finished paper are very high both in terms of the
quality of writing and the level of scientific analysis and literature
documentation. A sample of a published paper will be provided illustrating
the prescribed layout and style for your paper.You are encouraged to use
the library and all other resources available.
The formal report should be typed, double-spaced, and approximately 5-10
pages in length. Be concise, complete, and sure that the paper reads in
a logical progression of topics and information.
A variety of computer resources are available for your use in preparing
the formal report, including programs for drawing chemical structures and
importing them into text documents. See the Organic
Chemistry Tool Kit for links and information about some of these. Take
advantage of the Computer User Rooms on campus (e.g. in the University
Center).
The Formal Report is due on November 3 at 5:00 p.m.
Laboratory Final Exam
A Final Exam for the Organic Chemistry I Laboratory (Chem 334) will be
self-administered in the Open Lab during the final week of the semester.
The exam will be worth 40 points and will cover understanding of organic
laboratory techniques, procedures, methods for product analysis, and general
laboratory practices. The lab final will be a closed-book test, taken under
the spirit of academic honesty, and overseen by the Open Laboratory Faculty
Supervisors.
Academic Policies
I expect that all of your work for credit will be done strictly in the
spirit of academic honesty. I trust that each one of you will conduct your
work with the highest level of integrity. Furthermore, I expect that each
of you will assist in maintaining an atmosphere of honesty by bringing
to my attention any lapse in academic honesty you observe. Any breach of
academic honesty will receive a severe academic penalty. If cheating occurs
on any piece of graded work, the minimum penalty will be an automatic grade
of zero for that assignment. At the instructor's option a grade of E
may be assigned for the entire course. In any case, after an incident of
academic dishonesty has occurred a student will not be allowed to withdraw
from the course. Falsification of data is a serious offense in research,
industrial, and academic settings, and it will be treated as such.
Now with regard to authorized collaboration, it is expected that you
will likely discuss experiences about the labs with each other. Each person
is to conduct their own experiments, however. Work is to be done individually
in the Organic Laboratory. You should feel free to share advice, tips,
etc., and make use of the same when you conduct an experiment, but the
data you obtain, the notes you write, and the samples you prepare should,
of course, be generated by yourself through your own work. You may work
with each other when you are answering asigned exercises, much the way
you might when you work homework problems. You can learn by helping each
other to answer these exercises. However, you must share in the development
of answers rather than simply use work done by other individuals. You must
give proper credit in your notebook to any person whose input has been
utilized.
Grading
| Weekly Reports |
355 Points |
| Notebook Check |
20 Points |
| Formal Report |
100 Points |
| Lab Final Exam |
40 Points |
| Grand Total |
515 Points |
Late reports of all types will be penalized by 10% per day (maximum of
half off). Please note that the last day to withdraw from a class and receive
a refund is September 22. The last day to withdraw (no tuition
refund) and receive a W grade is November 22. Grade disputes
are subject to policies of the Natural Sciences Division.
University Policy
If you need course adaptations or accommodations because of a documented
disability, if you have emergency medical information to share with me,
or if you need special arrangements in case the building must be evacuated,
please make an appointment with me as soon as possible (Rieke 240, X8314),
and please contact the Coordinator for Students with Disabilities (Alene
Klein, Counseling and Testing Office, Ramstad Hall 106, X 7206).
Official notification to the instructor of any disability conditions that
may impair a student's academic performance must come from the Coordinator
for Students with Disabilities. Without advance warning, such difficulties
can not be used later as the basis for requesting make-up course work or
reconsideration of grades.
334sy_00.html
Last Modified 9/8/00
Copyright 2000, Craig B. Fryhle
|| PLU Department of Chemistry
||
Pacific Lutheran University