Chemistry 421
Advanced Organic Chemistry
Spring 2008
Instructor: Dr. Jeremy Wessel Office: Bea 206
Office Phone: (985) 448-4504 E-mail:
Office Hours: 9:40-11:40 MWF, 1:00-4:00 T, 10:30-11:30 R, 1:00-3:00 F
Catalog Description: CHEM 421. Advanced Organic Chemistry. 3-3-0. Prerequisite: CHEM 304 or permission of department head. A study of reaction mechanisms, stereochemistry, molecular rearrangements, and other selected topics. (40.0504)
Prerequisite: CHEM 304 or permission of the department head
Required Texts and Other Materials: Advanced Organic Chemistry: Reactions and Mechanisms by Bernard Miller, 2nd ed. (2004)
Required Supplemental Readings: None
You may want a copy of Organic Chemistry as a Second Language by David Klein as a review of Organic I and II.
Course Goals:
The student will develop an understanding of:
1. Pericyclic reactions and the Woodward-Hoffmann rules
2. Linear free energy relationships
3. Rearrangements of carbanions, free radicals, and electron-deficient species
4. Carbenes, carbenoids, and nitrenes
Student Outcome Objectives
At the end of the class the student will be able to:
· Be able to draw orbitals and energy level diagrams for linear polyenes
· Identify pericyclic reactions as electrocyclic, cycloaddition, or sigmatropic rearrangement
· Draw correlation diagrams for selected pericyclic reactions
· Apply aromatic transition state theory to pericyclic reactions
· Use the Woodward-Hoffmann rules to predict whether a pericyclic reaction is allowed or forbidden
· Give the products of pericyclic reactions
· Use the Hammett equation and Hammett plots to gain insight into reaction mechanisms
· Give products and write mechanisms for rearrangements of carbanions, free radicals, and electron-deficient species
· Give products and write mechanisms for reactions involving carbenes, carbenoids, and nitrenes
Course Content:
Chapter 1: Introduction
Mechanisms of Reactions, Electron Delocalization and Resonance
Chapter 2: Electrocyclic Reactions
Conrotatory and Disrotatory Processes, Explanations for the Woodward-Hoffmann Rules, Electrocyclic Reactions with Odd numbers of Atoms, Photochemical Cyclizations
Chapter 3: Cycloaddition and Cycloreversion Reactions
Suprafacial and Antarafacial Addition, Selection Rules for Cycloaddition and Cycloreversion reactions, Photochemical Cycloadditions. Omit problems 2b-d, i, 3c-d
Chapter 4: Sigmatropic Reactions
Theory of sigmatropic shifts, experimental observations, sigmatropic rearrangements of charged systems. Omit problem 3f
Chapter 5: Linear Free-Energy Relationships
The Hammett equation, Separation of Polar, resonance, and steric effects
Chapter 8: Rearrangement of Carbanions and Free Radicals
Carbanion rearrangements, rearrangements of free radicals, the Bergman and Meyers-Saito reactions
Chapter 9: Carbenes, Carbenoids, and Nitrenes
Formation of Carbenes and Nitrenes, Singlet and Triplet Carbenes, Addition to Double Bonds, Insertion Reactions, Rearrangements
Course Requirements:
2 hour exams (100 pts. each) covering ch 2-4 and 5,8,9 200 pts.
Quizzes on ch. 2, 3, 8 (20 pts. each) 60 pts.
Final exam (comprehensive) 200 pts.
Chapter problems (5 pts. per chapter) 35 pts.
Presentation on a selected topic 50 pts.
545 pts.
Method of Evaluation: Grades will be determined using the following scale:
A: 90-100 B: 80-90 C: 70-80 D: 60-70 F: <60
This scale may be adjusted downward if the class average is low.
Make-up Policy: Missed exams should be made up as soon as possible. Exams can be made up for an excused absence only.
Attendance Policy: No excuses are necessary for missing class. The student is responsible for making up any missed work. Attendance is essential to doing well in the course.
Academic Honesty Policy: Anyone found cheating will be subject to the penalties stated in Student Code of Conduct including but not limited to a score of zero on exam, expulsion from the class or expulsion from the University.
Semester Withdrawals: The last day to withdraw from the class with a ‘W’ is April 4, 2008.
Academic Disabilities Policy: If you have a documented disability that requires assistance, you will need to register with the Office of Disability Services for coordination of your academic accommodations. The Office of Disability Services is located in Peltier Hall, Room 100-A. The Phone Number is (985) 448-4430 (TDD 449-7002).
Class Disruptions are not tolerated. The use of cell phones, pagers and/or any other electronic personal device in class is prohibited. Any infractions will result in the dismissal from class.
1. Academic Grievances:
The proper procedure for filing grade appeals or grievances related to academic matters is listed in Section 5 of the Code of Student Conduct and at the following link: http://www.nicholls.edu/documents/student_life/code_of_conduct.pdf.
2. Continued Learning following an Extreme Emergency:
In order to make continued learning possible following an extreme emergency, students are responsible for:
• reading regular emergency notifications on the NSU website;
• knowing how to use and access Blackboard (or university designated electronic delivery system);
• being familiar with emergency guidelines;
• evacuating textbooks and other course materials;
• knowing their Blackboard (or designated system) student login and password;
• contacting faculty regarding their intentions for completing the course.
Faculty are responsible for:
• their development in the use of the Blackboard (or designated) software;
• having a plan for continuing their courses using only Blackboard and email;
• continuing their course in whatever way suits the completion of the course best, and being creative in the continuation of these courses;
• making adjustments or compensations to a student’s progress in special programs with labs, clinical sequences or the like only in the immediate semester following the emergency.