Organic Chemistry 302L
Spring 2011
PURPOSE
The purpose of the lab is to give you the opportunity to integrate your knowledge of organic chemistry, lab and
lecture. This term in lab you will be given a vial that contains about 5 g of an unknown organic compound.
These samples are direct from the bottle but should not be considered to be pure. You are to identify the
unknown, then design and carry out synthetic processes to convert your unknown into a derivative that must
be analyzed to prove that it is the desired product and that it is pure.
PROCEDURE
You are to identify the unknown using chemical, physical and spectral properties of the unknown. For positive
identification you must have at least 8 criteria, of which two must be spectroscopic. But as a chemist you
should recognize that the more proof you have, the easier it is to support your conclusions.
The chemical, physical, and spectral properties of organic compounds are useful in identifying both the
functional groups on compounds and the compounds as a whole as long as the compounds are pure.
Therefore, you should either have proof that the unknown is indeed pure or purify the unknown before you
attempt to determine its properties.
Once the identity of the unknown has been determined, you are to synthesize one derivative from your
unknown. Each derivative must be analyzed in the same way that your unknown was. You need to "prove"
that you made the desired derivative with at least five criteria (but more would be better) of which two must be
spectroscopic.
Before the derivative can be made, a formal, typewritten proposal must be submitted. Before you begin to
write your proposal you should be sure that you have identified your unknown correctly. You may “guess” at
the identity of your unknown before you start research on your proposal. If you correctly identify your
unknown you will be awarded the full 15 pts. If you “guess” incorrectly you will lose 5 of the 15 pts. for each
incorrect “guess”. Therefore you will have three chances to correctly identify your unknown before all of the
points for the unknown are forfeit.
PROPOSAL
The proposal may be any length in any font. (See paper grading for hints as to what should be included.) It
must be thorough, concise and complete and must contain the following in order:
1) The identity of the unknown.
2) The evidence for your conclusions on the identity of the unknown. (All of your spectroscopic, physical
and chemical evidence should be included along with a brief but thorough explanation of each of your spectra
and lab tests and a brief but thorough discussion of how you came to your conclusions.)
3) The derivative you intend to make.
4) The procedure you intend to follow to make the derivative. (This section should include reactions and
mechanisms, chemicals needed, proposed reaction conditions and references; essentially everything needed
to explain how you will synthesize your derivative and how you will meet all of the criteria by making it. Any
“green” experiments should be detailed here. Chemical structures and formulas may be hand written or
written on the computer program.
5) References. References are done in the same way you did them in your report last term. We use the
accepted style of the American Chemical Society (ACS) and can be found in any current major chemistry
journal like The Journal of Organic Chemistry (JOC) or The Journal of The American Chemical Society
(JACS) both of which can be found in the library or online. You may reference internet sites by listing the
complete internet address.
6) Hazard Report. Information on the physical properties and hazards associated with all chemicals you
used and intend to use in your reactions should be included as an appendix. (This should be updated as
procedures and chemicals change during the course of the experiment.) A list of internet sites that have
hazard listings is on my home page.
7) Spectra of your unknown should be compared with published spectra from internet or library sources.
Copies of the published spectra should be included as an appendix to your proposal. Spectral interpretation
should also be included in the appendix. A list of some internet sites that have spectra is on my home page.
A model proposal is posted on Moodle.
DERIVATIVES
The derivatives are to be made under the following guidelines:
1) All reactions and all reagents are to be approved by the instructor prior to the synthesis.
2) The derivative must contain at least one carbon more or less than the unknown.
3) The synthesis must contain at least three synthetic steps if a carbon-carbon bond is formed or four
synthetic steps if a carbon-carbon bond is not formed.
4) Each synthetic sequence (not each step) should produce at least 100 mg of purified product.
5) Purification, protonation, or deprotonation do not count as synthetic steps.
6) Additional unknown may be obtained in 5 g aliquots, but for each additional 5 g you need, 5 pts. will
deducted from your lab grade.
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7) Successful “greening” of any of your experiments will add a maximum bonus of 10 pts. to your lab grade.
DERIVATIVE REPORT
The report for the derivatives is also to be a typewritten formal report that is to be styled according to current
chemical literature. (See JOC or JACS for reference.) The report should include in order:
1) Abstract – The purpose of the abstract is to provide enough information so another scientist can read the
abstract and decide whether he or she should read the entire paper. An abstract is a brief summary of what
was attempted and what was found. Written in third person, past tense. This is normally not more than a few
sentences and no more than two paragraphs. A copy of this must be handed out to the class on the day
of the oral report.
2) Introduction - A brief description of what was attempted, what methods were used and why the
experiments were performed. This is much longer and more detailed than the abstract.
3) Results - A brief discussion of the results of your experiments. Written in third person, past tense. Were
the experiments successful? What were the yields?
4) Discussion - The formal discussion of the experiments. Written in third person, past tense where
appropriate. Here the results should be amplified and other issues (better ways to perform the experiments,
suggested improvements and changes, reactions and mechanisms (if known), and discussion of spectral,
chemical and physical evidence you have for verifying the synthesis of you derivatives) should be discussed.
If you performed any “green” chemistry it should be explained here – what you did and what made it ‘green”.
5) Conclusions - What knowledge was gained from the experiments and the experience?
6) Experimental - The most important part of the report. Written in third person, past tense. Each
experiment should be unambiguously and explicitly described so that someone who has never performed this
experiment could follow it and perform it in the lab. Usually only successful experiments are included, but
negative results may be included if the failed experiments provide some useful information such as "This is
not the way it should be done because I blew up half the lab".
7) References – Use the same style as last term. This is the accepted style of the ACS and can be found
in any current major chemistry journal like The Journal of Organic Chemistry or The Journal of The American
Chemical Society both of which can be found in the library or online.
8) Hazard Report - Information on the physical properties and hazards associated with all chemicals and
reactions should be included as an appendix. (This should be the updated version.) Parts of this (or all of it)
may be copied from your proposal. A list of internet sites that have hazard listings is on my home page.
9) Appendix - Spectra of your unknown and derivatives and published spectra (of both your unknown and
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derivative) form internet or library sources (if you can find them) should be included as an appendix. Any
spectra included should have a detailed spectral analysis attached. A list of some internet sites that have
spectra is on my home page.
A model report is posted on Moodle.
This report, your meticulously thorough lab notebook and the original, graded copy of your proposal are
required for your final, formal report.
VERBAL REPORT
You will also be required to give a formal verbal report to your peers. The report should last 8-10 minutes and
should include in order:
1) A brief discussion on how you identified your unknown. Include spectra, chemical and physical data. (1-2
minutes)
2) A brief discussion of what derivative you were going to make and why you specifically chose that
derivative. (1-2 minute)
3) A discussion of what you did for each derivative. Included should be all pertinent reactions and proof that
you made (or did not make) the desired derivative. Also explain any “greening” of the procedure.(5-7 minutes)
4) Conclusions. A very brief section on the important "discoveries" of your project. You should include an
explanation of how you fulfilled the criteria for derivative synthesis. (1-2 minutes)
5) References should be included as they are needed on the bottom of the slides, pages, screens, etc.
where the data is referenced.
Scientists traditionally use visual aids to convey information. Visual aids may be in the form of models,
posters or slides (35 mm or overhead). Slides are commonly used to express reaction or mechanism
schemes, show experimental data, equipment diagrams, and list items (objectives, results or conclusions).
Handwritten overhead slides may be used for your presentation.
PAPER GRADING: Papers will be graded based on content, accuracy, completeness, use of evidence, use
of visual aids (chemical equations, illustrations. etc.), proper citation style and to a lesser extent grammar,
person, tense and sentence structure. Complete sentences with proper use of chemical terminology (jargon),
proper grammar, and correct spelling are expected. Mechanisms, chemical equations, and illustrations are
used to clarify ideas and arguments and should be used where appropriate. Late papers will be docked 10
pts. per week.
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IMPORTANT DATES
January 11-13
Feb. 8-10
March 7-11
April 19-21
April 26-April 28
Check-in, obtain unknowns
Proposals Due at Noon
Spring Break
Verbal reports will be given during your assigned lab. Derivative reports are due
at that time.
Check-out
GRADING
Identification of unknown (with supporting report and data)
Proposal
Synthesis of derivative (with supporting data)
Verbal report
Final report
Total
5
15 pts
20 pts.
30 pts.
15 pts.
20 pts.
100 pts.