Oakland University

College of Arts and Sciences

Department of Chemistry

Advanced Organic Chemistry - CHM 534

FALL SEMESTER 2010
3 Credits, course reference 13411,
M W 5:30 - 7:17 pm, 187 SEB
Roman Dembinski
PREREQUISITE
CHM 235 (Organic Chemistry II)
Important: Each student is expected to have a thorough command of thall material in the organic
chemistry sequence. The text used last year was
"Organic Chemistry" 5 edition and "Study Guide
and Solutions Manual - Organic Chemistry" 5th edition by P. Y. Bruice, Pearson/Prentice Hall &
Sons, Upper Saddle River, NJ, 2007. Several Organic Chemistry textbooks are equivalent, to
name a few:
Brown&Foote&Iverson&Anslyn, Bruice, Carey, Clayden&Greeves&Warren&Wothers, Ege, Hornback, Jones, London, McMurry, Solomons&Fryhle, Smith, Sorrell, Vollhardt,
Wade.
TEXT
As textbook "Advanced Organic Chemistry Reaction Mechanisms" by Bruckner,
Harcourt/Academic Press 2002 (ISBN: 978-0-12-138110-3) has been formally assigned.
The Advanced Organic Chemistry Reactions and Mechanisms, 2nd edition, by Miller,
Pearson/Prentice Hall 2004 (ISBN-10: 0130655880 ISBN-13: 9780130655882) and "Perspectives
on Structure and Mechanism in Organic Chemistry" by Carroll, Brooks/Cole Thomson Publishing
Company, 1998 (ISBN-10: 0534249485 ISBN-13: 9780534249489; new edition to be published by
Wiley in March 2010) are relevant books, and chapters from these and other books will also be
incorporated into the class program.
"Advanced Organic Chemistry", 5th edition, Part A: Structure and Mechanisms (ISBN: 978-0-38768346-1) Part B: Reactions and Synthesis (ISBN: 978-0-387-68350-8) by Carey and Sundberg,
Springer Verlag 2007 (hardcover) and 2008 (softcover), perhaps the most comprehensive textbook
at the market addresses the need of organic chemistry majors.
"Marchs Advanced Organic Chemistry Reactions, Mechanisms, and Structure" (ISBN 978-0-47172091-1) by Smith, March, 6th edition, Wiley, 2007 is a good reference book.
LECTURES
Homework problems will be reviewed and worked out in detail. You are encouraged to come with
specific questions from lectures, the text, and assigned problems.
OFFICE HOURS
There is no office hours. The instructor (SEB 225) prefers walk-ins. The instructor is also available
on weekends (call in advance), but not later than 7:30 pm.

MIDTERM
Monday, March 1

EXAMINATIONS

FINAL
Wednesday, April 21, 7:00 10:00 PM
COURSE GRADING
Homework will count as 30% of the course grade, the midterm exam 30% and the final will count
as 40% of the course grade. Ranking (distribution curve) will be posted. "Wild Card Rule": The
instructor reserves the right to factor presentations into the final grades (maximum of 10%).
LECTURES PLAN
1. Stereochemistry
2. Conformational, steric, and stereoelectronic effects
3. Nucleophilic substitution
4. Addition and elimination reactions
5. Aromatic substitution
6. Reactions of carbonyl compounds
7. Carbanions
8. Pericyclic reactions
9. Organic reactions mechanisms
10. Free radical reactions
11. Photochemistry
12. Asymmetric synthesis
13. Synthesis: the disconnection approach
14. Total synthesis

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