Organic Reaction Mechanisms (Chem 5202)
Fall 2012
Instructor: Prof. Bill Wuest, 448 Beury Hall
Phone: 215-204-7167
email:
W: 5:30-8:20pm
Course Schedule (tentative and subject to change): Readings
Aug. 29:Review of Organic Chemistry/Stereochemistry KC Pg. 350
Sept. 5:Bonding/Hyperconjugation CSA Chap. 1 & 2
KC Pg. 220, 222, 406, 408, 410
Sept. 12:Baldwin’s Rules/Acyclic Conformations CSA Chap. 3
KC Pg. 162, 300, 342, 386
Sept. 19:Conformational Analysis Handout
KC Pg. 158, 190, 416, 480
Sept. 26: Reaction Mechanisms/pKa CSA Chap.4, 7 & 8
Acid-Base Chemistry KC Pg. 8, 24, 48, 54, 86, 138, 150, 158, 162, 190,
192, 202, 242,286, 298, 350, 384, 416, 442, 444, 480
Oct. 3:Substitution and Elimination Reactions CSA Chap. 5-6
KC Pg. 66, 72, 96, 102, 108, 170, 188, 206,
238, 294, 336, 356, 412, 476, 484, 500
Oct. 10:Aldol Reactions CSB Chap. 1 & 2
KC Pg. 8, 52, 74, 128, 162, 166, 202, 280
320, 344, 374, 384, 414, 432, 442, 456, 480
Oct. 17: Olefination ReactionsKC Pg. 10, 36, 104, 110, 154, 212, 214,
230, 344, 452, 454, 486, 488
Oct. 24:Radical ReactionsCSA Chap. 12 & 13
KC Pg. 44, 46, 208, 240, 276, 492
Oct. 31:Pericyclic Reactions/FMO Theory CSA Chap. 11
KC Pg. 6, 20, 22, 32, 88, 90, 98, 122,
126, 132, 205, 304, 324
Nov. 7:Pericyclic Rearrangements (cont.)
Nov. 14:Diels-Alder Reaction/Aromaticity CSA Chap. 9;CSB Chap 6
KC Pg. 56, 126, 140, 176, 178, 204, 216, 394
Nov. 21:Thanksgiving (No Class)
Nov. 28:Enzymatic Reactions/Biosynthesis Handout
Dec. 5:Mechanism Review Class Student Presentations
Dec. 12: FINAL EXAM
Grading: 25% Quizzes; 25% Paper Review; 25% Classroom-Lead Discussion; 25% Final Exam
Textbooks:
(1)Advanced Organic Chemistry, Fourth Edition – Part A by Francis Carey and Richard Sundberg: ISBN - 978-0306462436 (CSA) (5th edition available online at
(2)Advanced Organic Chemistry, Fourth Edition – Part B by Francis Carey and Richard Sundberg: ISBN - 978-0306462450 (CSB) (5th edition available online at
(3)Strategic Applications of Named Reactions in Organic Synthesis by Laszlo Kurti and Barbara Czako: ISBN -978-0124297852 (KC)
Specific Goals and Objectives:
The primary goal of this course is to introduce the student to advanced principles in organic reaction mechanisms and further develop their critical thinking skills to both rationalize and predict reactivity within complex molecule synthesis. These goals will be attained through the better understanding of chemical bonding, reactivity, structure, and function of organic molecules. Basic and advanced principles in bonding theory, conformational analysis, reactivity, and orbitals will be taught to aid in these objectives. Ultimately, the student will be able to rationalize the reactivity of a group of starting materials, predict the mechanism by which the transformation proceeds, and be able to identify the product.
Student Learning Outcomes:
Students will be able to:
- Draw lowest energy structures of organic compounds
- Illustrate reaction mechanisms
- Identify named reactions and predict the products
- Identify aromatic, homo-aromatic, non-aromatic and anti-aromatic compounds
- Draw transition states and mechanisms of substitution, elimination, olefination, radical, pericyclic, and enzymatic reactions
- Discuss mechanisms and rationale behind reactivity
- Propose experiments to verify reaction pathways
- Verbally communicate organic chemistry principles and defend their rationale
- Present mechanisms to their peers
- Critically review papers from the literature
Blackboard™: A Blackboard site is set up for this course. Please check that you are registered and can access this course on Blackboard™. Announcements and e-mails will be sent out via Blackboard™ so it is imperative that you check this web site and your Temple email account on a regular basis. Supplemental materials, messages and schedule adjustments will be posted there. Class rankings will be posted on this site so you can get a feel for how you are doing in the course.
Attendance:Your attendance at all lectures is expected and essential to your success in this course. In case of emergency, please notify me by email and we can arrange to meet at an alternate time.
Academic Integrity: All students are expected to adhere to the highest levels of academic integrity. Any students found cheating (i.e. copying answers to exam, quiz, or homework; taking credit for work that they did not perform) will receive a failing grade in the course. They will also be reported to the Dean's office in the College of Science and Technology. There are dire consequences. Please do not give cause to suspect cheating. Cheating can be detected during and after tests are handed in.
Disability Resources and Services: Any student who has a need for accommodation based on the impact of a disability should contact their instructor privately to discuss the specific situation as soon as possible. Contact Disability Resources and Services at 215-204-1280 in 100 Ritter Annex to coordinate reasonable accommodations for students with documented disabilities.
Lecture Class: All readings should be completed before they are scheduled to be discussed in the lecture (see attached calendar). This is your preparation for the lecture class. If you don’t understand the material after you have read it, the lecture may clarify the material. If you still don’t understand the material, you can ask questions during the lecture. Please turn your cell phones off.
Testing Policy: The final exam will bein a "Closed Book" environment. No books, notes, or reference material may be consulted during any test. You can use model sets during the exam. 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 this course. Electronic devices, including calculators, phones, and PDA's are not permitted in the exam room. You will be held responsible for all the material and assigned problems in the scheduled chapters, except for any sections that your instructor specifically tells you that you may exclude. Cell phones are to be turned off during exams.
Exams: There will be onein-class final exam. Exam questions will be in a similar format to class and quiz problems. The final exam will be 25%and is cumulative, covering ALL material taught in this course.
Quizzes: The quizzes given during the semester are designed to prepare you for examinations and to make sure you understand key materials and concepts.Quizzes will be handed out and completed every week and will account for 20% of your grade. Quiz questions will be very similar to the problems in the book and cover the material in the readings. In addition, each student will be responsible for teaching a mechanism in the last class. This assignment will account for 5% of your grade.
Classroom-Lead Discussion: Each student will be required to lead a one-hour mechanism-based discussion during class (either alone or in a pair). Topics will be selected at random on the first day of class and the student is responsible for selecting the questions, guiding the discussion, and emphasizing key points of the lecture. An outline of the discussion must be reviewed and approved by me no later than 5pm on the Monday before the discussion!
Mechanism Paper Review: There will be one critical review of a paper due Oct. 17worth 25% of your grade. Each student will select a paper that critically analyzes a reaction mechanism from the literature and will discuss the selection with me by Sept 26. Once the paper is agreed upon the student will critically review the methods presented in the paper and provide critiques concerning alternative experiments, design flaws, highlights and lowlights. The review is expected to bewritten in a scientific manner and judge if the paper should have been accepted for publication.
Final Notes: This course is designed to be very demanding and it is in the student’s best interest to be prepared for each class (i.e. complete all assigned readings). Each course will be subdivided into three modules. The first module will involve a primary lecture on the material highlighted in the course schedule. The second module will include strategically selected problems that will be worked out by the students in class. The intent of this module is to instruct “through doing” and highlight common mistakes made my graduate students. Do not be afraid to be wrong! I will illustrate key points through these problems and focus on important concepts. The third module will be an in-class quiz, which typically will involve three questions. The students will work on the problems either individually or in groups and then each present an answer to the class.