Chemistry 421 – 2T
Advanced Organic Chemistry
Spring 2010
Instructor: Dr. Jeremy WesselOffice: Pel 245C
Office Phone: (985) 448-4504E-mail:
Office Hours: 10:00-12:00 MWF, 1:00-2:00 MW, 10:30-11:30 TR
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.
Prerequisite: CHEM 304 or permission of the department head
Required Texts and Other Materials:Pericyclic Reactions– A Textbook by S.Sankararaman,
Wiley-VCH, 2005
Required Supplemental Readings: None
Optional Materials:You may want a copy of Organic Chemistry as a Second Language by
David Klein as a review of Organic I and II.
Student Outcome Goals and 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, sigmatropic rearrangement, cheletropic, or ene
- Draw correlation diagrams for selected pericyclic reactions
- Apply frontier orbital theory to pericyclic reactions
- Apply aromatic transition state theory to pericyclic reactions
- Use Woodward-Hoffmann rules to predict if a pericyclic reaction is allowed or forbidden
- Give the products of pericyclic reactions
Course Content:
Chapter 1: Molecular Orbitals and their Symmetry
Molecular Orbitals, Molecular Orbitals of Conjugated Polyene Systems, Symmetry Elements and
Symmetry Operations
Chapter 2: Electrocyclic Reactions
Definition and Classification, Stereochemistry, Woodward-Hoffmann rules, Frontier orbital
method, Orbital Symmetry Correlation Method, Transition State Aromaticity Method
Chapter 3: Cycloaddition Reactions
Definition and Classification, Stereochemistry, Woodward-Hoffmann rules, Frontier orbital method, Orbital Symmetry Correlation Method, Transition State Aromaticity Method, 2+2
cycloadditions, Diels-Alder, 1,3-dipolar cycloadditions, Higher Order Cycloadditions
Chapter 4: Sigmatropic Reactions
Definition and Classification, Stereochemistry, Woodward-Hoffmann rules, Frontier orbital method, [1,x] sigmatropic rearrangements, [3,3] sigmatropic rearrangements, [2,3] sigmatropic
rearrangements
Chapter 5: Cheletropic, Group Transfer, and Ene Reactions
Definitions, Woodward-Hoffmann rules for Cheletropic Reactions, Classification of Ene Reactions
Method of Evaluation:
Handouts are 5 pts. each for a total of 60 pts. 3 hour exams (Ch. 1-2, 3, 4) for a total of
300 pts.Final exam is worth 200 pts. Presentation on a selected topic will be 50 pts. Total 610.
Grading scale:A: 90-100B: 80-90C: 70-80D: 60-70F: <60
This scale may be adjusted downward if the class average is low.
Academic Dishonesty Policy: Any student 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.
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.
Make-up Policy: Missed exams should be made up as soon as possible. Exams can be made up
for an excused absence only.
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).
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:
Continued Learning following an Extreme Emergency
The following guidelines are meant: to help the business of education continue at NichollsStateUniversity in the aftermath of an extreme emergency situation; to help faculty and students understand their roles in completing education requirements for courses in progress when the emergency began; and to encourage faculty to be imaginative and resourceful in finding ways to
continue the education of students and the work of the university.
Faculty responsibilities:
• Faculty members are responsible for their development in the use of the Blackboard software.
• Faculty members are responsible for having a plan for continuing their courses using only Blackboard and email.
• Faculty members should be allowed to continue their course in whatever way suits the completion of the course best, and encouraged to be creative in the continuation of these courses.
• Any adjustments or compensations made to a student’s progress in special programs with labs, clinical sequences (i.e. Culinary, Nursing, etc.), or the like should be made only in the immediate semester following the emergency.
- Faculty members are responsible for including these guidelines in all syllabi.
Student responsibilities:
• Students are responsible for reading regular emergency notifications on the NSU website.
• Students are responsible for knowing how to use and access Blackboard.
• Students are responsible for being familiar with emergency guidelines.
• Students are responsible for evacuating textbooks and other course materials.
• Students are responsible for knowing their Blackboard login and password
• Students are responsible for contacting faculty regarding their intentions for completing the
course.
NOTE: Faculty and students should be open, flexible, and show compassion in determining the
precise course of action.
Semester Withdrawals: The last day to withdraw from the class with a ‘W’ is March 31, 2010.
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.