Chem 334
Spring 2008
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
<>
handouts on IR and Mass spec
are posted at the Chem 332 website
<>
Teaching Assistants for
this course
David Gerstenhaber, dagers@UDel.Edu
Weiwei Tian, tvv@UDel.Edu
Michael Taylor, mttaylor@UDel.Edu
Gabriela Uceda, guceda@UDel.Edu
Sections for
this course
Section 010: Monday 12:20PM -
3:20PM, Tuesday 12:30PM - 3:30PM, TA=Tian
Section 011: Monday 3:35PM - 6:35PM, Tuesday
3:30PM -
6:30PM, TA=Gerstenhaber
Section 012: Monday 7:00PM - 10:00PM, Tuesday
7:00PM - 10:00PM. TA=Taylor
Section 013: Wednesday 7:00PM
- 10:00PM, Thursday 12:30PM - 3:30PM, TA=Uceda
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
Links:
Chem
332 Spring 2008
Chem
332 Spring 2007
Chem 334 Spring 2003
Chem 334 Spring 2005
Chem
332 Spring 2006
Prof.
Taber's course page for Chem 334 (previous years)
Chem
333
Chemical
Database Searching Tutorials
• Intro to Beilstein Handout from
Chem 333 (Dr. Koh, lab 7)
<>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
• Handout:
Introduction
to substructure
searching on Beilstein
Commander
• Handout:
Introduction to Reaction searching with substructures on Beilstein
commander
Powerpoint
presentations:
• IR handout
• Mass Spec and
UV-Vis handout
Grading
There will be two lab exams that together will
constitute 50% of your grade. The rest of your grade will be based on
your lab grade and on your performance in the independent study. 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
Lab exams will be given on Monday March 17 and Monday,
April
28 from 7–10 pm in 101 Brown Labs. IF YOU
HAVE A CONFLICT WITH THESE TIMES, PLEASE CONTACT ME TO ARRANGE A
SEPARATE TIME TO TAKE A MAKEUP EXAM. Those in the Honors
section must also take the lab exams.
The Exams will cover spectroscopy and arrow-pushing mechanisms, and
will
be open book and open notes. Be sure to study exam questions from
earlier years (see links above).
Last year's lab exam
Exam
1 2007 Answers to Exam 1 2007
Exam 2 2007
Answers to Exam 2 2007
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, April 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
example, giving every single peak in an IR spectrum would not be very
useful, but pointing out that your ketone product has a peak at 1715
cm–1 in the IR spectrum is useful 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.
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. 11th - 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
(see the sample checklist).
1 Week of Feb 18th: Session 1, Beilstein TA office hours in the
HHMI room. Session 2, Spectroscopic identification of an
unknown. Your lab report is
due next week to your TA.
2 Week of Feb 25th; Both sessions:
Synthesis of Acetylferrocene (Acetylferrocene)
[Chp. 7A pg 67-70 of Bell, Clark and Taber (BCT)]. Week 1 lab report is due during the first
session.
NOTE: Proposed Independent Study due 10 a.m. Monday Feb 25th
3 Week of March 3rd.
Friedel-Crafts
Reaction (Friedel-Crafts
Acylation) [pg 237-239 of BCT] During second session, start: Chp.
31 Photochemical Reactions D (Benzopinacol);
4 Week of Mar 10
Session #1: Finish
Benzopinacol
Session #2: Chp.
37 A2,
A3 Heterocycle Synthesis, p 293-5
5 Week of March 17th
Session #1. Lab
Exam
Session #2. Chp. 29 D Amines
<>6 Week
of
March 24th
Session #1: Chp. 28A Nucleophilic
Aromatic Substitution, p 249-51 - save your product for session 2!
Session #2: Chp. 30 AB Chemiluminescence
Spring Break
7 Week of April 7nd Both sessions:
Independent
Study
8 Week of April 14th Both sessions: Independent
Study
9 Week of April 21th. Both
sessions:
Independent Study
<>10 Week
of
April 28th
Session #1: Lab
Exam
Session #2: Ester Hydrolysis–recycling polyethylene
terephthalate; Start Orange Peel Esterase
11 Week of April 30th
Session #1: Finish Orange Peel Esterase
Session #2: Begin Biofuel
12 Week of May 7
Session #1: Finish Biofuel
Session #2: Clean up, check out