Chem 334

Spring 2006
Lecture MWF, 10:10-11 AM in 101 Brown Labs

Professor Joseph M. Fox
272 Brown Labs
302-831-0191
jmfox@udel.edu

Office hours: Mondays 11-12, or by appointment.  Contact me by email to schedule an appointment

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handouts on IR and Mass spec are posted at the Chem 332 website


Teaching Assistants for this course

Allison Kimball, akimball@UDel.Edu
James Plampin, plampin@UDel.Edu
Xie Xiaocong, xcxie@UDel.Edu
John Young, youngjo@UDel.Edu

Textbooks:
Organic Chemistry Laboratory, Third Edition by Bell, Clark and Taber
 

Links:
Chem 332
Chem 334 Spring 2003
Chem 334 Spring 2005
Prof. Taber's course page for Chem 334 (previous years)

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Chemical Database Searching Tutorials

• Handout: Beilstein Introduction
• Handout: Introduction to structure searching on Beilstein Commander
• Handout: Introduction to substructure searching on Beilstein Commander
• Handout: Introduction to Reaction searching with substructures on Beilstein commander
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Powerpoint presentations:
• IR handout
• Mass Spec and UV-Vis handout
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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
7-10 p.m. Monday March 13 and Monday, April 24.  Location to be announced. All sections will meet together, including the Honors Organic lab section!. During the weeks of exams, the first lab session will not meet (i.e. the monday labs for sections 010 and 011; the wednesday lab for section 012, and the tuesday lab of section 013).  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).

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.

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. 6th - Develop a plan for your Independent Study project.  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 13th: 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 20th;  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 20th   

3  Week of Feb 27th. 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 6
    Session #1: Finish Benzopinacol
    Session #2: Chp. 37 A2, A3 Heterocycle Synthesis, p 293-5  

5 Week of March 13th
    Session #1.  Lab Exam 7-10 p.m on Monday, March 13.  Room TBA. All sections together!
    Session #2.  Chp. 29 D Amines

<>6 Week of March 20th
    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 3th Both sessions: Independent Study

8 Week of April 10th  Both sessions: Independent Study

9 Week of April 17th.  Both sessions: Independent Study

<>10 Week of April 24th
    Session #1:  Lab Exam 7-10 p.m on Monday, April 24.  Room TBA All sections together!
    Session #2:  Start Orange Peel Esterase

11 Week of May 1
    Session #1: Finish Orange Peel Esterase
    Session #2: Begin Biofuel


12 Week of May 8
    Session #1: Finish Biofuel
    Session #2: Clean up, check out