Chemistry 534 Fall 2012 Advanced Organic Chemistry (Physical Organic: Structure and Mechanism)

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1 Chemistry 534 Fall 2012 Advanced Organic Chemistry (Physical Organic: Structure and Mechanism) California State University Northridge Lecture: Instructor: Dr. Thomas Minehan Office: Science 2314 Office hours: TR 12:00-1:00 pm E.mail: Class Meetings: Required Texts: Course Web Site: TR, 5:00 pm 6:15 pm Eucalyptus Hall 2227 Anslyn and Dougherty, Modern Physical Organic Chemistry Robert Grossman, The Art of Writing Reasonable Organic Reaction Mechanisms Prerequisite for Enrollment in Chemistry 534 A passing grade in Chemistry 334 or its equivalent Course Focus: This class will focus on organic structure and mechanism and the tools physical organic chemists use to uncover the features of reaction mechanisms. In the first half of the course, we will study three broad areas of physical organic chemistry: molecular structure and thermodynamics, reactivity and kinetics, and the theory and applications of electronic structure. A main focus of the second portion of the course will be addressing modern mechanistic problems from the original chemical literature in problem-solving format. The class will culminate in student presentations on reaction mechanisms, focusing on how the tools of physical organic chemistry were used to study these mechanisms.

2 Student Learning Outcomes for Chem 534 (B.S. and M.S. Program): SLO1(m): Demonstrate basic knowledge in the area of organic chemistry. (Assessment tool: course exams) SLO2(m): Organize and communicate scientific information clearly and concisely, both verbally and in writing (Assessment tool: final project/presentation). SLO3(m): Effectively utilize the scientific literature to research a chemistry topic (Assessment tool: final project/presentation) Grading: Midterm Exam: 30% (150 pts) Final Exam (cumulative): 30% (150 pts) Presentation: 30% (150 pts) Mechanism Practice: 10% (50 pts) Total: 500 pts. *Grades: %: A, 84-70% B, 79-60% C, 50-60% D Exams: The midterm will focus on the first half of the course and will involve questions based on literature articles. The final exam will emphasize reaction mechanisms. Mechanism practice: For the second half of the course, practice mechanistic problems will be placed on the course website before the week of class; these should be printed out and worked on prior to coming to class. During class, these mechanisms will be worked on in groups and solutions presented by students on the board. Presentation: Each student will choose an approved reaction and give a short (20 minute) presentation based on the original literature. The presentation will focus on the tools used to study the reaction of their choice and the conclusions reached about the mechanism. Students should turn in an outline of their presentation one week prior to the presentation, and a bibliography and a copy of their slides on the day of their presentation. *Attendance: Attendance in the lecture is mandatory *Drop/ Withdrawal Policy: The chemistry department adheres to the university policy concerning withdrawal from the course. A full description is published in the university catalog for the dates fixed for adding, withdrawal, etc. Academic failure does not constitute a clear and compelling reason for withdrawal from class or for the assignment of an incomplete grade after the date for withdrawal, as specified in the University catalog, is passed.

3 Make up exams are normally not given, and will be considered only under very compelling and unusual circumstance and when proper documentation is provided in support of such a request. Cheating: Cheating on an exam will result in failure on that exam plus possible disciplinary action by the Dean of Students. In any instance of academic dishonesty the University s disciplinary procedures will be followed. Common Journal Abbreviations: JACS = Journal of the American Chemical Society; JOC=Journal of Organic Chemistry; TL=Tetrahedron Letters; Tet=Tetrahedron; ACIEE=Angewandte Chemie International Edition in English; OL=Organic Letters

4 Chemistry 534 Course Schedule Dates Topics Reading Aug. 28 Review, Mechanism G, Ch.1 Grossman Ch1. problems 1-5 Aug. 30, Sept. 4 Structure and Bonding A&D, Ch.1 A&D, Problems Ch. 1: 9, 15, 19, 21, 27 + website problems Sept. 6, 11 Conformation, Sterics, Strain A&D, Ch.2 A&D, Problems Ch. 2: 6, 10, 20, 34, 35, 44 + website problems Sept. 13, 18 Stereochemistry A&D, Ch.6 A&D, Problems Ch. 6: 9, 16, 17, 29, 22 + website problems Sept. 20, 25 Thermodynamics & Kinetics A&D, Ch.8 A&D, Problems Ch.8: 11, 12, 14, 15, 18, 19, 20, 21, 24, 25, 27 Sept. 27, Oct. 2 Kinetics / Catalysis A&D, Ch.7 A&D, Problems Ch. 7: 9, 13, 16, 17, 18; Ch. 9: 6, 10, 13, 14, 15, 16, 17 + website problems Oct. 4, 9 Catalysis A&D, Ch. 9 A&D, Problems Ch. 9: 6, 10, 13, 14, 15, 16, 17 + website problems Oct. 11, 16, 18 Solutions and Non-Covalent Binding Forces A&D, Ch. 3, 5 A&D, Problems Ch. 3: 9, 10, 12, 13, 25 + website problems A&D, Problems Ch. 5: 9, 14, 15, 19, 21 + website problems Oct. 23 Midterm Oct. 25, 30 Cationic reactions/ mechanism practice G, Ch. 3 Nov. 1, 6 Anionic Reactions/ mechanism practice G, Ch. 2 Nov. 8, 13 Radical, Pericyclic/ mechanism practice G, Ch. 4,5

5 Nov. 15, 20 Organometallic mechanisms / practice G, Ch. 6 Nov. 27, 29 Student Presentations Dec. 4, 6 Student Presentations Dec. 11 Final Exam