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Chem 497A Organic Reaction Mechanisms Fall 2011

A proposed mechanism can never really be proven; rather it is a case of alternative mechanisms being eliminated. Carey & Sundberg

Course Overview & Objective: This course focuses on the study and analysis of selected electronpushing mechanisms of organic reactions. Students will be able to identify reactive sites in starting materials, be familiar with the function of reagents, and predict the products of organic reactions. The format of the course consists of students solving problem sets and sharing their answers during class time. Prerequisite: Chem 212. Instructor: Dr. Katherine Masters 218 Whitmore Lab 863-3319 kmasters@psu.edu Office hours: By appointment

Class Meetings: Mondays & Wednesdays at 4:40 pm to 6:00 pm in 104 Osmond Course Web: Course materials will be posted on the course ANGEL site. Required Textbook: The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd edition by Robert B. Grossman; 2003, Springer-Verlag New York, Inc. ISBN 0-387-95468-6 Recommended Texts: Advanced Organic Chemistry. Part A, Structure and Mechanisms (5th Edition). Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry. Part B, Reactions and Synthesis (5th Edition). Carey, F. A.; Sundberg, R. J. Marchs Advanced Organic Chemistry (5th Edition) Smith, M. B.; March, J.

Attendance & Class Participation: Problem sets will be given throughout the entire semester, and each student will be assigned specific questions for each problem set. Students will be asked to present their answers by drawing out their mechanisms on the chalkboard and discussing their rationale behind their approach. For this reason, attendance and class participation is worth 20% of the final grade. The instructor will also be looking to see if students improve (or not improve) over the semester; it will be considered when determining final grades.

Exams: Three exams will be given during class time; each exam is worth 20% of the final grade. There will be a comprehensive final exam for this class; it is worth 20% of the final grade. The exam dates are: Exam 1 Exam 2 Exam 3 Final Exam Monday, September 26; Polar reactions under basic conditions (Chapter 2) Monday, October 17; Polar reactions under acidic conditions (Chapter 3) Monday, November 7; Pericyclic reactions (Chapter 4) TBD by the university scheduling system; comprehensive exam including freeradical reactions (Chapter 5)

Important Registrar Dates: Regular Drop Deadline Regular Add Deadline Late Drop Deadline Wednesday, August 31 Thursday, September 1 at 8:00 am Friday, November 11

Academic Integrity: The PSU Faculty Senate Policies for Students briefly defines academic integrity as the pursuit of scholarly activity free from fraud and deception and is an educational objective of this institution. Academic dishonesty includes, but is not limited to, cheating, plagiarizing, fabricating of information or citations, facilitating acts of academic dishonesty by others, having unauthorized possession of examinations, submitting work of another person or work previously used without informing the instructor, or tampering with the academic work of other students. It is expected that you will behave in accordance with these principles, which are explained more fully at the site: http://www.science.psu.edu/academic/Integrity/index.html. Matters of academic dishonesty will be turned over to the University disciplinary system for appropriate disciplinary action. The College of Sciences Code of Mutual Respect & Cooperation can be viewed at http://www.science.psu.edu/climate/code-of-mutual-respect-and-cooperation-1/.

Tentative Schedule of Class Meetings


The following schedule is a tentative outline of the semesters activities and assignments. Updates, if any, will be announced and posted on ANGEL. Week 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Monday 8/22 In-Class Activity; Read Chapter 1 Wednesday 8/24 8/31 In-Class Discussion Problem Set 1 Discussion

8/29 Problem Set 1 Discussion 9/5 9/12 9/19 9/26 10/3 10/10 10/17 10/24 10/31 11/7 11/14 11/21 11/28 12/5 No Class Labor Day Problem Set 2 Discussion Problem Set 3 Discussion Exam 1 Problem Set 4 Discussion Problem Set 5 Discussion Exam 2 Problem Set 6 Discussion Problem Set 7 Discussion Exam 3 Problem Set 8 Discussion No Class Thanksgiving Problem Set 9 Discussion Review; Do Chapter 7 Questions

9/7 Lecture Polar reactions under basic conditions; Read Chapter 2 9/14 9/21 Problem Set 2 Discussion Problem Set 3 Discussion

9/28 Lecture Polar reactions under acidic conditions; Read Chapter 3 10/5 Problem Set 4 Discussion

10/12 Problem Set 5 Discussion 10/19 Lecture Pericyclic reactions; Read Chapter 4 10/26 Problem Set 6 Discussion 11/2 Problem Set 7 Discussion

11/9 Lecture Free-radical reactions; Read Chapter 5 11/16 Problem Set 8 Discussion 11/23 No Class - Thanksgiving 11/30 12/7 Problem Set 9 Discussion No Class (431W Poster Session)

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