Advanced Organic Chemistry
Mechanism
Spring 2006

I. 03-401-1 Mechanisms in Organic Chemistry

Prerequisite: 03-225; 03-300 or 03-325
Lecture Hours: T 6:30-9:15 PM

Instructor: Dr. Salim M. Diab
Phone: Office: 815-836-5393 (Lewis)
Office: 815-740-3855 (St. Francis)
Home: 815-730-8302
Fax: 815-740-4285
E-mail: sdiab@stfrancis.edu
HomePage: http://www.stfrancis.edu/ns/diab/etherman.htm

II. Course Description: This course will emphasize the use of mechanistic outlines in describing organic chemical reactions. The course will familiarize students with the principles governing organic reactivity and provide an understanding of organic chemistry that is impossible to secure by memory alone. Indeed, creative students might be able to predict reaction products for organic reactions they have never seen before and be able to design new reactions for complex organic synthesis.

Objectives: Upon successful completion of this course, students should be able to:
1. grasp how elementary reactions in organic chemistry occur;
2. understand reaction mechanisms which would serve as a guide in the design of synthetic sequences;
3. investigate current chemical research in organic chemistry; and
4. predict new reaction mechanisms and new synthetic sequences.

III. Required Text:
Writing Reaction Mechanisms in Organic Chemistry, 2nd Edition; Audrey Miller and Phillipa Solomon, Academic Press, 2000.

Required Supplements:

Lecture Notes Manual

Solved Problems Manual

Unsolved Problems Manual

Other References:
1. Organic Reaction Mechanisms, 2nd. edition, Ronald Breslow, W. A. Benjamin, 1969.
2. A GuideBook to Mechanism in Organic Chemistry, 6th. edition, Peter Sykes, Longman, 1986.
3. Journal of the American Chemical Society, (JACS).
4. Writing Reactions Mechanism in Organic Chemistry, Audrey Miller, Academic Press 1992.
5. Electronic Interpretation of Orqanic Chemistry, A Problem Oriented Text, Fredric M. Menger and Leon Mandell, Plenum, 1980.
6. Pushing Electrons, A Guide for Students of Organic Chemistry, 2nd edition, Daniel Weeks, Saunders, 1995.
7. Mechanism and Structure in Organic Chemistry, Edwin Gould, Holt, Rinehart and Winston, 1959.
8. Reaction Mechanisms in Environmental Organic Chemistry Richard Larson and Eric Weber, Lewis, 1994.

Web Sources:
http://monomerchem.com/display4.html (name reactions)
http://orgchem.chem.uconn.edu/namereact/named.html (name reactions)
http://www.chemhelper.com/mechanisms.html (basic mechanisms)

http://www.columbia.edu/itc/chemistry/c3045/index.html?client_edit/course_slides.html(Intensive Organic Chemistry)

http://chemistry.boisestate.edu/rbanks/organic/nomenclature/organicnomenclature1.htm (Nomenclature Tutorial)

http://chemistry.boisestate.edu/rbanks/inorganic/bonding%20and%20hybridization/bonding_hybridization.htm (Bonding and Hybridization)

http://chemistry.boisestate.edu/rbanks/organic/resonance.html (Resonance)

http://chemistry.boisestate.edu/rbanks/organic/mechanisms.html (Mechanisms)

http://chemistry.boisestate.edu/rbanks/organic/synthesis/synthesis.html (Synthesis)

Computer Sources:
Organic Reaction Mechanisms, CD, Falcon Software, Inc.

IV. Expectations of Students:
1. Homework assignments (workbook and name reactions).
2. Journal assignments - read selected article from current issues of JACS and write a brief commentary on at least four different mechanisms.
3. Final Exam - Take Home

Breakdown for Grading:

Mechanisms 30%
Name Reactions 30%
Journal Assignments 20%
Final Exam (Take Home) 20%
Total                                           100%

Topics to be Covered from your Text:

Ch. 1 - Introduction:
            Basic Concepts in Organic Chemistry
Ch. 2 - General Principles for Wrting Reaction Mechanisms
Ch. 3 - Reactions of Nucleophiles and Bases
Ch. 4 - Reactions Involving Acids and Other Electrophiles
Ch. 5 - Radicals and Radical Anions
Ch. 6 - Pericyclic Reactions

Sample Name Reactions in Organic Chemistry

-Aldol Condensation and Crossed Aldol
-Baeyer Villiger Oxidation
-Barton Reaction
-Beckmann Rearrangement
- Birch Reduction
-Cannizzaro Reaction
-Chugaev Reaction
-Clalsen Ester Condensation
-Claisen Rearrangement
-Claisen Schmidt Reaction
-Clemmensen Reduction
-Cope Elimination
-Cope Rearrangement
-Corey Seebach Synthesis
-Corey Posner Synthesis
-Curtlus Degradation or Rearrangement
-Darzens Reaction
-Diels Alder Reaction
-Dieckmann Reaction
-Favorsfy Rearrangement
-Friedel Crafts Reaction
-Gabriel Synthesis
-Galterman Kock Reaction
-Gomberg Reaction
-Grignard Reagent
-Hell-Volhard-Zelinski Reaction
-Hofmann Elimination
-Hofmann Rearrangement
-Hunsdiecker Reaction
-Ingold Mechanism
-Kiliani Fischer Synthesis
-Kolbe Reaction
-Knoevenagel Condensation
-Leuckart Reaction
-Lobry de Bruyn Alberda van Ekenstein Transformation
-Lossen Degradation or Rearrangement
-MacLafferty Rearrangement
-Mannich Reaction
-Markovnikov Addition
-Meerwein Ponndorf Reaction
-Meisenheimer Complexes
-Michael Addition
-Oppenauer Oxidation
-Perkin Condensation
-Pinacol Pinacolone Rearrangement
-Reformatsky Reaction
-Reimer Tiemenn Reaction
-Sandmeyer Reaction
-Saytzeff Elimination
-Schmidt Rearrangement
-Simmons Smith Synthesis
-Skraup Synthesis
-Stobbe Reaction
-Stork Enamine Reaction
-Tschitschibabin Reaction
-Wagner Meerwein Rearrangement
-Wolff Rearrrangement
-Wolff Kishner Reduction
-Williamson Synthesis
-Wittig Reactlon
-Whitmore Mechinism
-Whitesides House Synthesis
-Wurtz Reaction

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