Advanced Organic Chemistry

Chemistry 406;  Spring 2008

 

 

 

INSTRUCTOR:          Prof. Tom Mitzel

                                    Office:  Clement Chemistry, #111, phone 297-5244

                                                e-mail: thomas.mitzel@trincoll.edu

 

                                    Office Hours:  M-F  7:30-8:30 AM

                                                            Th 8:30-9:55 AM, or just stop by!

 

                                    Home Phone:  478-1404 (before 9:30 pm)

 

SCHEDULE:              Lecture:           Tuesday, Thursday 6:15-7:30 PM Clement 308

                                   

TEXTBOOKS:           Advanced Organic Chemistry, Part B, 4th Edition, Carey and Sundberg

                                    Molecular Model Kit

 

SUPPLEMENTAL     Students are encouraged to read other chemistry texts found in the

READING:                 library or available from the instructor.  A list of good books is given below

 

                                    1)         Modern Synthetic Reactions (House)

                                    2)         Organic Synthesis (Fuhrhop/Penzlin)

                                    3)         Advanced Organic Chemistry (March)

 

SYLLABUS:              We will be covering the following topics during the course of the semester.

 

                                                Reading Journal Articles/Presentation of Journal Articles

 

                                    Topics from Carey and Sundberg:

 

 

                                                Chapter 1:        Alkylation of Nucleopohilic Carbon Intermediates

Chapter 2:        Reaction of Carbon Nucleophiles with Carbonyl Group

Chapter 3:        Functional Group Interconversion by Nucleophilic Substitution

Chapter 4:        Electrophilic Additions to Carbon-Carbon Multiple Bonds

                                                Chapter 5:        Reduction of Carbonyl and Other Functional Groups

Chapter 6:        Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations

Chapter 7:        Organometallic Compounds of the Group I, II, and III Metals

Chapter 10       Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediates

 

 

Other chapters as time permits      

 

EVALUATION:         biweekly Problem Sets, Weekly Paper, Two Exams, Presentations, and

                                    Class Participation will make up your final grade.  The final breakdown will follow the guideline shown below.

 

                                    Weekly Problem Sets/Paper:               20%

                                    Two Examinations:                             30%

                                    Presentations:                                      20%

                                    Class Participation:                              5%

                                    Final Examination:                              25%

 

 

 

TENTATIVE              First Mid-Term           February 23

EXAM DATES:         Second Mid-Term       March 28

                                    Final Exam                  TBA

 

PAPERS:                    Every other week, you will be responsible for selecting an article from the recent literature (within the last 6 months) to read and summarize.  You will turn in a 1-3 page summary of the paper to me at the end of the week.  This paper should summarize what the author was trying to do, why the author was attempting to work in this area, and should include any significant mechanistic steps, historical context etc.  These papers are considered part of your weekly problem sets, and may substitute fully for problem sets on some weeks.

 

                                    I will give the topic for the paper (it will generally be related to what we are discussing in lecture) and you will be able to choose from the Journals listed below.

 

                                    1)         Journal of the American Chemical Society

                                    2)         Journal of Organic Chemistry

                                    3)         Tetrahedron Letters

                                    4)         Tetrahedron Asymmetry

                                    5)         Synthetic Communications

                                    6)         Synthesis

 

                                    If you find an article from a different journal that you think may fall within the guidelines, show me the article, and if it does, then you may use that article.

                                   

 

PRESENTATIONS:   Each week, there will be 1-2 presentations presented in the class.  These will be given on the day the papers are due, and will be a presentation of the paper you read and summarized.  You should keep this in mind when you are reading your article and writing up your paper for me each week.  The presenters will not be picked in any certain order, so you may be picked on any given week to present your paper to the class.  Your presentation should be about 15 minutes in length, and most of it will be given on the chalkboard.

 

                                    If you are not presenting during any particular week, you are expected to hand in two written questions on the paper.  These questions need to be detailed and well thought out.  Since this is a seminar course, I encourage you to not only write your questions down, but to ask them of the speaker as well.

 

COMMENTS:           This course will be taught as part lecture and part seminar.  As such, your attendance is crucial to the success of the class, and your participation in lectures will be counted toward your final grade.  Since this is a senior level course, you will be expected to work independently to a certain extent.  You should feel free to read any material on the topics covered which will help in your understanding of the course.