Professor Joseph M. Fox
272 Brown Labs
302-831-0191
jmfox@udel.edu
Labs are held in Rm 318 Drake
Office hours: Mondays 11-12, or by
appointment.
Contact me by email to schedule an appointment
Teaching
Assistants
for
this
course
Danielle McAtee, dmcatee@udel.edu
Anil Pandey, pandey@UDel.Edu
Sha Bai, baisha@UDel.Edu
Safety You Must Have Safety Goggles No Shorts No Open Toed Shoes No Food or Drink Come Prepared, Read the Assignment, and Bring your Notebook Textbooks:
Organic Chemistry Laboratory, Third Edition by Bell,
Clark and Taber
Learning
Goals for this Course
Through
successful
completion of this course:
1) Students will learn safety procedures in
the organic lab
2) Students will learn how to document experiments in a notebook
3) Students will learn how to interpret material safety data sheets
4) Students will know how to setup and analyze a diverse range of
organic chemistry experiments, monitor their progress, purify products,
and analyze their purity.
5) Students will learn how to purify products using
crystallization, distillation, column chromatography
6) Students will learn how to analyze spectral data using IR
spectroscopy, 1H NMR spectroscopy, 13C NMR
spectroscopy, and polarimetry.
7) Students will learn how to determine the purity of substances
using
TLC, melting point analysis in addition to the above spectral
techniques
8) Students will develop an appreciation for green chemistry
through
experiments
9) Students will learn how to use spectroscopy to reveal the
structure
of an unknown substance
10) Students will participate in an independent study, wherein
they
research a two-step chemical synthesis. Students will learn how
to utilize chemical databases to research the
scientific literature, and will use modern spectroscopic techniques to
determine the successfulness of their independent projects.
<>The following handouts demonstrate how to do more advanced
searches with Beilstein. Although they show the old Beilstein
interface, the concepts are the same with the new interface.
Especially important (for the independent study) is the reaction
searching using substructures
Grading
There will be a lab exam that will
constitute 33% of your grade. The rest of your grade will be based on
your lab grade (34%) and on your performance in the independent study (33%). Before each lab, you will be given a short (5 min)
quiz by your TA, in which you will demonstrate your preparedness. You
will turn in your notebook
at the end of each lab period. Your TA will grade it and return it to
you
promptly.
Handouts
As needed to supplement the text will be posted on the
course Web site.
Lab Exams
A Lab exam will be given (time and date TBA). Those
in the Honors
section must also take the lab exams.
The Exams will cover spectroscopy and structure elucidation, and
will
be open book and open notes. Be sure to study exam questions from
earlier years (see links below).
Final Report for the
Independent study
The report for the independent study must be typed, and it roughly
follows the format for a full paper written to an American Chemical
Society journal. Chemical structures (and reagents that
accompany those structures) may be drawn by hand. Presentation,
grammar, spelling and writing style will count! Your final report
is worth 50 points (to be averaged with the points that you receive
from your TA). The independent study will be initially reviewed
by your TA, and then graded by me. Please turn your report in to
your TA on Friday,
29th. Revisions may be neccessary, and
will be due one week after it is returned to you.
Sections of the report:
Introduction:
Write a brief introductory statement (license to use your creative
writing skills here). Using chemical structures, show the
reaction that you carried out. Provide references in the
following format: Authors, "Title of Article" Journal Name Year, Volume
Number, pages. You should also detail the accepted mechanism for
each of the reactions that you studied.
Results and
Discussion:
Briefly explain what you did experimentally, and if you consider the
experiment to have been successful. While reagents and reaction
times are appropriate for discussion, don't talk about all of the nitty
gritty details. Do elaborate on any differences between what you
did and what was published. Unless they are of special importance,
leave out discussion of filtering procedures, volumes of solvents, and
work up procedures. State if your product was purified by
chromatography, but don't tell me the chromatography solvents or the
number of test tubes that you collected. Basically, in this
section you describe and discuss what you found without boring us with
the details. We can find those in your lab notebook pages.
Discuss details of how the spectroscopic information
supports the
assignment of your structure, the purity of the material, etc. It
should not be a description of every single data point. For IR
data, you should discuss peaks associated with major functional
groups. For example, pointing out that your ketone product has a
peak at 1715
cm–1 in the IR spectrum is important information. Similarly,
pointing out that you observed a peak at 202 ppm in the 13C NMR would
also be relevant for discussion. Any other information that
serves to support your findings (e.g. melting point in agreement with
the literature; TLC evidence ; color of the compound is in agreement
with the literature) should also be discussed.
For NMR data, you should provide tables with detailed
peak assignments,
including a discussion of multiplicity.
Conclusions:
Tell us
if your reactions worked, and if they would be suitable for
incorporation into the regular undergraduate lab. Briefly
support your statements.
Supporting
Information:
Provide an appendix with hard copies of any spectra (NMR, IR, etc);
provide copies of the articles that you used. Also, please
photocopy the pages from your lab notebook and include those pages in
the appendix.
Protective Equipment
Goggles are required and must be worn at all times in
the laboratory. Suitable clothing must also be worn.
0 Week of Feb. 8 - Develop a plan for
your
Independent
Study project. Use Beilstein to find
suitable precedent. You need to turn in a
copy of
the articles that you wish to adapt. Follow the guidelines set
forth
on the following checklist (for an
example, see this sample checklist)
1 Week of Feb 15:
Session 1, Beilstein TA office hours
in 222
BrL.
Session #2: Chp.
37
A1,
A2
Heterocycle
Synthesis,
p
293-5.
Start
Benzopinacol
NOTE: Proposed Independent Study due to your TA in
the first lab session of Monday Feb
22th
6 Week
of
March 22
Session #1: unknown
Suzuki
Session #2:
Chp. 28A Nucleophilic
Aromatic Substitution, p 249-51
Spring Break
7 Week of April 5nd Both sessions:
Independent
Study
8 Week of April 12th Both sessions: Independent
Study
9 Week of April 19th. Both
sessions:
Independent Study
10 Week
of
April
26th
Session #1: lab does not meet--study for Lab
Exam
Session #2:
Chp.
30
AB
Chemiluminescence
11 Week of May 3. Independent
study final report due to your TA at the first lab session.
Session #1:
Chp.
30
AB
Chemiluminescence
Session #2: tropinone