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Chemistry 261 Section 1
CHE 261 - Organic Chemistry II Lab
Spring 2010
Lectures: M, W, F (9:10 – 10:00 am), M11
Laboratory: T (8:10 am – 12:00 pm), JE325
Lecturer: Adiel Coca, Ph.D.
Office: 304 Jennings Hall
Phone: 203 – 392 - 6982
E-mail: cocaa2@southernct.edu
Office Hours: T (3:30 – 4:30 pm), W & F (10:10 am – 12:00 pm) or by appointment
Required Texts:
 Pavia, D. Introduction to Organic Laboratory Techniques: a Microscale
Approach, 4th ed. (Custom edition available in bookstore)
 Goggles (available from chemistry club).
 Hardcover bound lab notebook.
Your laboratory grade is based on the following criteria:
 Each pre-lab quiz: 20 points.
 Each informal (title, results, discussion, and conclusion sections only; when
necessary also include sample calculation, bibliography, and attachment sections)
lab report is worth 50 points.
 Each formal (all sections) lab report is worth 100 points.
 Notebook keeping and lab safety: 100 points. Points may also be deducted from
final total for repeated safety violations.
 8-10 minute presentation: 100 points.
Students must obtain at least a passing grade (≥60%) in the laboratory component of the
course and perform every experiment in order to pass the course.
Attendance:
Absolutely mandatory! Making-up labs will be almost impossible since most sections are
completely filled.
Academic Integrity:
All forms of academic dishonesty will not be tolerated. Such infractions are considered
cause, at the least, for awarding a grade of "0" on the quiz or lab report in question. For
more details, see the student handbook on the subject. This policy will be strictly
enforced.
Student Disabilities:
I believe in providing reasonable accommodations for students with documented
disabilities on an individualized and flexible basis. If you are a student with a
documented disability, the university’s Disability Resource Center (DRC) determines
appropriate accommodations through consultation with the student. Before you may
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receive accommodations in this class, you will need to make an appointment with the
Disability Resource Center, located in EN C-105A. To speak with me about other
concerns, such as medical emergencies or arrangements in case the building must be
evacuated, please make an appointment as soon as possible.
Safety:
Laboratory safety is the number one priority, follow the safety guidelines at all times.
Safety goggles must be worn at all times. No shorts, skirts, or open-toed shoes are
allowed in the laboratory. No eating or drinking in lab. Wash skin immediately if you
come in contact with any chemicals. Always wash your hands before leaving the lab.
Inform the instructor of any spill or accident immediately.
Waste disposal:
Place all waste material in the proper disposal container found in the waste hood. Only
water and soap may go down the drain.
Notebooks:
Save the first few pages of the notebook for a table of contents, which gives each
experiment title and pg # where it begins in your notebook. The table of contents as well
as everything else in the notebook should be updated weekly. Only use pen and don’t
skip pages. Number all pages. On the first page of a new experiment, give the date and
experiment title. Give a brief purpose to the experiment. Record any changes to the
experimental steps that were performed. Make note of any observations of the reaction
and product(s) (color, solid/liquid, soluble/insoluble, reaction conditions). Specify
amounts for reactants and products. Report mp or bp if they were measured. Make any
calculations in your notebook such as percent yield, percent recovery, and retardation
factor. Attempt to explain any unexpected result. Results in the notebook must match
those in reports that are turned in. At the end of each laboratory period, the instructor
must sign at the bottom of the most current page. Notebooks may be collected at any time
during the semester for inspection.
Presentation:
The presentation can be on any organic topic such as those covered this semester in lecture and
lab or in a peer-reviewed article. The presentation must be around 8-10 minutes. You may have a
partner covering the same topic, but each must present for about 8-10 minutes. Examples of
topics include organic reactions, instruments, lab techniques, among others (see instructor for
approval). The presentation should start with background (definitions and historical facts) and
end with applications. For example, if a reaction is your topic, you may want to include the
following: the most general form of the reaction, historical facts (if known) such as the name of
the discoverer, the mechanism, specific examples, stereochemistry and regiochemistry (if
appropriate), related reactions (if there are) and how they differ, and some applications (if
known) such as in the synthesis of a drug or other commercial product. You may even include
data and observations from a lab experiment you performed. Presentations should be done on
PowerPoint or on transparencies. Cite any sources used at the bottom of each slide. Structures
can be drawn by hand (neatly!) and scanned into the PowerPoint presentation or drawn with
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ChemDraw (software is available in Jennings 306). Turn in a printout of your slides to the
instructor before (recommended) or on the day of the presentation.
Report Guideline:
It is important to keep the following in mind:
The purpose of the lab report is to communicate to others the results
and conclusions you obtained in performing an experiment. You
should explain why the experiment was performed, how it was
performed, what results were obtained, how the results were analyzed,
and what conclusions were reached.
Format and style are detailed in the Chemistry 120 Laboratory Manual, pages 120-124.
The items highlighted below are of particular importance:
General: Reports must be typed and double spaced. Number every page in the top-right
corner. Always use significant figures in data obtained in the lab and in calculations.
Remember to reference sources for all literature information you include in your report.
Use a superscript number to identify the citation. Names of chemicals are not capitalized.
Pay attention to grammar, spelling, style, and word usage. Bold or underline section
titles. Avoid using words such as I, we, you, etc. Don’t start a sentence with a number
unless it is written out (two instead of 2 is acceptable) because the period may be
confused with a decimal point. Write concisely and proofread your report before handing
it in!
Title: Should reflect the report’s content, and should be both brief and specific.
Abstract: Include a statement (2-3 sentences) about the purpose of the project. Discuss all
of the techniques, instruments, and reactions being studied. For reactions, discuss how the
product will be characterized.
Introduction: Provide a brief background (theory & current knowledge in the field on the
subject) of the experiment. Define any “new” term such as a new technique you learned
in a sentence or two. Draw important chemical and theoretical equations. You may hand
draw chemical structures. Draw a reaction mechanism for important chemical
transformations. Define each term in theoretical equations. Cite any source used.
Experimental: Provide a brief, but specific summary of the procedure, reagents used,
weights, times, temperatures, etc. Use your own words, do not copy the lab manual. Use
third person (passive voice) and past tense: “The reaction mixture was heated at 50 oC for
2 h. Then the benzoic acid was recrystallized from 20 mL of H2O.” Since you will be
following a procedure, always cite the source at the top of the section. Don’t start
sentences with numbers.
Results: Include every relevant data collected such as amounts of chemicals (pure,
impure, reactants, and products) used. Don’t give weights of flasks or beakers used to
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weigh them. Organize data in tables or figures when necessary. Tables and figures should
be numbered and include a descriptive heading. Always calculate Rf values when TLC is
used.
Sample Calculations: Show one sample calculation of % yield, % recovery, and any other
significant calculation. Use significant figures. This section is not required if there are no
calculations.
Discussion: This is the most important section of the report. The purpose of the
discussion is to interpret and compare the results. Discuss every piece of data collected.
Always comment on compound appearance (unknowns and products). Comment on
purity every time you take a mp or other technique that gives an assessment of purity.
Whenever possible compare your results with literature data. Include the literature value
as well as the source. Discuss sources of error. Be specific on the cause of the error.
Mathematical error is not an acceptable answer. Discuss all spectral data (IR, NMR) in
detail correlating every peak to a structural unit. For 1H NMR, discuss splitting pattern,
integration, and chemical shift. For IR, assign every major peak to a functional group
(OH, C=O, etc). Discuss retention times and peak area for GC data. Discuss TLC data
(purity, separation, extent of reaction, id of spots).
Conclusion: This is a concluding statement (4-5 sentences) that summarizes the key
points of the results and comments on the success or failure of the experiment. Suggest
further study or possible improvements to the experiment if warranted. Be objective;
point out the features and limitations of the work. Relate your results to current
knowledge in the field and to your original purpose in undertaking the project: Was the
experiment successful or not?
Bibliography: Cite any source using consecutively numbered footnotes. Include a
complete reference: All authors or editors, title of journal or book (italics), publisher (if it
is a book), year (bold), volume (italics), and inclusive pages:
1.
Demko, Z.; Sharpless, K. B. Journal of Organic Chemistry, 2001, 66, 7945-7950.
Resources for physical data:
Whenever possible use published reference books such as peer-reviewed journal articles, Aldrich
catalog, Handbook of Chemistry and Physics, and the Merck index. Only use the following
websites as a resource: Aldrich.com and chemfinder.com. Never cite Wikipedia.com in your
reports.
Attachments: Always attach a copy of any instrumental printout (IR, NMR, and GC). Hand draw
a structure of the compound(s) involved in every printout and label every important peak with a
structural assignment (functional group or proton). Also mark every printout with a figure
number and figure heading so that you may refer to it in the report. Also include a hand-drawn
copy of your TLC plates when used.
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Prentative Outline of Labs:
Dates
Project
Report Due
1/26
Check-in, no lab work
2/2
#20 Reactivities of Alkyl halides
2/9 - Informal
2/9
#25B 4-methylcyclohexene
2/23 - Formal
2/16
President’s day – no lab
2/23
#38B Benzoic acid
3/9 - Informal
3/2
#44B 1,4-diphenyl-1,3-butadiene
3/16 - Formal
3/9
#52 Luminol
3/30 - Informal
3/16
#30 Preparation of Soap
#49A, B, or C Polymers
4/6 - Formal
3/23
Spring break – no lab
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3/30
#47 Synthesis of Off
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4/6
#47 Synthesis of Off (cont.)
#64 Aldol/Michael
Approval of Presentation Topic
4/20 – Informal (#47)
4/13
#64 Aldol/Michael (cont.)
4/27 – Formal
4/20
#27 Relative reactivities of Aromatic Compounds
5/4 - Informal
4/27
#50 Diels-Alder reaction
5/11 - Informal
5/4
Check out/8-10 minute presentation – no lab work
5/11
No lab
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Late Penalty:
Lab reports will be penalized 10% for each day that they are late. Late reports will not be
accepted after the report has been returned to the rest of the class. Late reports can be dropped
off in my office (under the door if I am not around) or after CHE 261 lecture. E-mail attachments
will not be accepted and no report will be accepted after 5:00 pm on Wednesday, May 12.