Chem 334

Spring 2009

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

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

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Teaching Assistants for this course

Dave Boruta, dboruta@UDel.Edu
Peter De Matteo, tiamat@UDel.Edu
Gabriela Uceda, guceda@UDel.Edu

Sections for this course

Section 010: Monday 12:20PM - 3:20PM,  Tuesday 12:30PM - 3:30PM, TA=Uceda
Section 011: Monday 3:35PM - 6:35PM, Tuesday 3:30PM - 6:30PM, TA=DeMatteo
Section 012: Monday 7:00PM - 10:00PM, Tuesday 7:00PM - 10:00PM. TA=Boruta


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 2009
Chem 332 Spring 2008
Chem 332 Spring 2007
Chem 332 Spring 2006
Chem 332 Spring 2005
Chem 332 Spring 2003


Chem 334 Spring 2008
Chem 334 Spring 2006
Chem 334 Spring 2005
Chem 334 Spring 2003


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 Wednesday, March 18 and Wednesday, April 29 from 5–7 pm in 131 Sharp.    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).


Exam 1 2009     Answers to Exam 1 2009


Exam 2 2009     Answers to Exam 2 2009



Prior year's lab exams


Exam 1 2008     Answers to Exam 1 2008

Exam 2 2008       Answers to Exam 2 2008


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. 9th - 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 16th: 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 23th;  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 24th   

3  Week of March 2nd. 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 9
    Session #1: Finish Benzopinacol
    Session #2: Chp. 37 A2, A3 Heterocycle Synthesis, p 293-5  

5 Week of March 16th
    Session #1.  lab does not meet--study for Lab Exam
    Session #2.  Chp. 29 D Amines

<>6 Week of March 23th
    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 6nd Both sessions: Independent Study

8 Week of April 13th  Both sessions: Independent Study

9 Week of April 20th.  Both sessions: Independent Study

<>10 Week of April 27th
    Session #1:  lab does not meet--study for 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