TENTATIVE SYLLABUS FOR ADVANCED ORGANIC CHEMISTRY
Organic Structure and Mechanism
(Please consult http://www.temple.edu/chem-help for revisions.)

CHEMISTRY 321
Fall Semester 2001; TuTh 11:40 - 1:00 PM; BE415

Instructor: D. Dalton , BE340, Telephone 215-204-7138; Facsimile 215-204-1532
e-mail: dalton@temple.edu;URL: http://astro.temple.edu/~dalton
Office Hours: MWF 9:30-10:30 and TuTh 10:30-11:30

TEXTBOOK: Francis A. Carey and Richard J. Sundberg, "Advanced Organic Chemistry Part A: Structure and Mechanism", 4th Edition, 1999, Kluwer Academic/Plenum Publishers. is required.


You should read the required material noted in the calendar below before coming to class.


The purpose of this course is to carry you beyond the basic principles of organic chemistry. To succeed you will need to know and use the nomenclature of organic chemistry and you will need to be able to understand structural drawings and draw (not just look at and understand) stereochemical and minimum energy structural representations of some organic compounds. You will be learning more about the dynamics and reactivities of organic molecules than you did in your first one-year course and you will be expected to use the results obtained with spectroscopic tools to convince yourself (and others) that your arguments about structure and dynamics are substantive.



To succeed, you will find a need to refer to material that is not in your textbook. You will want to examine examples of reactions beyond those shown, syntheses related to those presented, elaboration of concepts beyond the presentation provided, etc. Any other advanced organic chemistry text and various compendia that can be found in Paley Library as well as the Chemistry Department Library are avialable to you. Additionally, there is a considerable amount of rather basic material available in any Organic Chemistry textbook to look at to refresh what you might have forgotten as well as "online" help (to which you might wish to refer from time-to-time). With regard to the latter, there is a more-or-less complete textbook called the "Virtual Textbook of Organic Chemistry" by Professor William Reusch at MSU, "Organic Chemistry OnLine" by professor P.R. Young at Illinois, and "WEB-sters' Organic Chemistry" from the Lawrence Livermore Laboratory to name just a few.

As time permits, I will place some additional material (instead of making copies for classroom distribution) on the Chemistry Honors-Majors Server which can be accessed from on-campus sites only. It is my understanding that this can be done for one semester for class use without violating copyright. Finally, in this vein, you will find that the text is heavily footnoted with literature references that served to allow the authors to make statements in the text. You are expected to utilize this material! Therefore, early in the term (see attached calendar) some time is set aside for a real (as contrasted to a virtual ) visit to the Chemistry Department Library.

Several modeling programs are available in the Department for molecular modeling studies (should you wish to try) and inexpensive sets of molecular models may be purchased in the T.U. Bookstore .


OTHER TOPICS OF INTEREST

PROBLEMS

A small number of problems (to be found at the end of each chapter) are shown as assigned (in the Schedule below) for the first few chapters of the text. This is done to help you face what might otherwise be overwhelming and to provide a basis for classroom discussion. You will profit from taking the time (as your schedule permits) to do additional problems. Answers (where they exist) to the problems can be found in the references provided (near the end of the text) and most of the reference material can be found the in the Chemistry Department Library . Some problems do not have (or have incomplete) answers but presumptions can be drawn from experimental results. Some reference material is not available. It is essential that you try to work through (at least) each problem assigned and to try to understand the theory/method used for its solution (where it has been solved).

As usual, there is too much material to be mastered in the time available. Nonetheless, it is important to do the work promptly so that when it is discussed you can contribute to the discussion ( vide infra ) .


Experience has shown that students who do more than the assigned problems do well in the course.


EXAMINATIONS and GRADING:

Grading is based upon classroom participation (i.e., blackboard work in class in response to homework problems) which is worth 200 points for the semester. In addition, there will be two 50 minute examinations worth 200 points each (for a total of 400 points) given during regular class time and a final examination worth 400 points (on Thursday, 13 December 2001; 11:00 AM - 1:00 PM ). The examinations are NOT multiple choice (the operating assumption being that if you know something you can write it down). Old examinations for this course are unavailable but the format will consist of a series of question similar to those presented at the end of each chapter. In that vein, all examinations are "Closed Book". No books, notes, models, computers, or reference material may be consulted during the test period. You will not need a calculator. As noted in the Student Handbook ..."Giving or receiving information during examinations is a violation of the Temple Student Discipline Code and will result, at minimum, in a grade of "F" for the course."

There will be no makeup examinations. If you miss an exam for any reason, your grade will be based on the work that you have completed.

PLEASE NOTE: I grade all of the examinations myself. I believe this helps me understand where you are having difficulties and where we can work to overcome them. The grading copy will be posted on the chem-help site (http://www.temple.edu/chem-help), on the Chemistry Honors-Majors Server which can be accessed from on-campus sites only and on my site shortly after the examination is given. Graded papers will be returned to you as soon as possible and I do not currently plan on discussing the examination in lecture unless you have questions after you have examined the grading copy.



INCOMPLETES/WITHDRAWAL ( as per University policy):

"Students may withdraw from a course without penalty (Grade of "W") any time up to and through Monday, 19 November."

The grade "I" (Incomplete) will be given only to students who have amassed 300 points or more. "Obtaining the grade "I" requires a signed form (available from your instructor or College academic advisors) indicating the reason for the grade "I" and stating specifically what work remains to be done and by what date the work will be completed. Failure to provide such a form will result in the grade "F" being submitted at the end of the term."


SCHEDULE

Chemistry 321 (August - December 2001)

Lecture on Tuesday; Problems on Thursday;
Week beginning:

Topic (Chapter in Carey and Sundberg)

Problems (in Carey and Sundberg)

27 August

Chapter 1 (Bonding and Structure) and Introduction to the Chemistry Library

Chapter 1 ; 1, 2, 3, 6, 11, 15, 16, 18, 24

3 September

Chapter 2 ; Stereochemical Principles

Chapter 2; 1, 3, 4, 5, 11, 15, 17, 20

10 September

Chapter 2 (continued); Chapter 3; Conformational, Steric and Stereoelectronic Effects.

Chapter 3; 2, 4, 5, 6, 7, 11, 18

17 September

Chapter 3; Conformational, Steric and Stereoelectronic Effects.

Chapter 3; 2, 4, 5, 6, 7, 11, 18

24 September

Chapter 4. The Study and Description of Reaction Mechanisms

First Exam Chapters 1-3.

1 October

Chapter 4. The Study and Description of Reaction Mechanisms

Chapter 4; 3, 6, 7, 11, 14

8 October

Chapter 5; Nucleophilic Substitution

15 October

Chapter 6; Addition and Elimination

22 October

Chapter 7; Carbanions

29 October

Chapter 8; Carbonyl Compounds

Second Exam Exam Chapters 1-7.

5 November

Chapter 9; Aromaticity

12 November

Chapter 10; Aromatic Substitution

19 November0

Chapter 11; Pericyclic Reactions

26 November

Chapter 12; Free Radicals

3 December

Chapter 13; Photochemistry

December 6, 2001 is a study day. Final examinations begin on Monday 10 December. The final examination for this course is scheduled for Thursday, 13 December 2001; 11:00 AM - 1:00 PM