CHEM 4311/6311: Intermediate Organic Chemistry

Students to be Served: Senior undergraduates and first year graduate students majoring in chemistry or a closely related discipline.


Satisfactory completion of a recent one year course in organic chemistry, equivalent to CHEM 3310 and CHEM 3511.  B or higher is highly recommended.


physical organic chemistry with an emphasis on structure and mechanism. (Three lecture hours per week, 3 credit hours)


Ted Burkey

Textbooks and other materials:

Required textbook: Sykes, P., A Guidebook to Mechanism in Organic Chemistry, 6th ed

  • A general organic chemistry textbook, Bruice for example, is recommended.

Course Objectives:

Review of general organic chemistry and more advanced treatment of structure and mechanism.

Course Schedule


Sykes CH1 problems Electronic Structure

Sykes CH2  problems Energetics Fundamental Mechanisms

Sykes CH3 problems  Lewis Structures, Acid-Base  Chemistry

Sykes CH4 problems Nucleophilic Substitution

Sykes CH5 problems Electron Deficient Centers

Sykes CH6 problems Aromatic Substitution

Sykes CH7 problems Electrophilic and Nucleophilic Addition

Sykes CH8 problems Carbonyl Addition

Sykes CH9 problems Elimination Reactions

Sykes CH10 Problems Carbanion Chemistry

Sykes CH11 Problems Radical Reactions

Sykes CH12 Problems Pericyclic Reactions

Sykes CH13 Problems Linear Free Energy Relationships


Three examinations and assignments will be given during the semester. Examinations for 6311 students will include more advanced problems. A comprehensive final examination will be administered in class at the assigned time. Each test and the sum of the assignments will count 20% toward the grade for the course.

7311 grades are expected to be in the range: A > 85 > B > 70 > C > 55 > D

4311 grades are 90% of the corresponding 7311 grades


  • Books and journals may be used to help with take-home tests, but assistance may not be sought from other students or faculty.
  • Tardiness and unexcused absence from class are unprofessional behaviors which should be avoided, but attendance will not be graded.
  • Electronic devices such as cell phones and pagers should be turned off in the classroom.
  • Reasonable and appropriate accommodations will be made for students who present a memo from Student Disability Services.

Academic Integrity and Student Conduct:

Expectations for academic integrity and student conduct are described in detail on the website of the Office of Student Judicial and Ethical Affairs(Student Accountability). Please take a look, in particular, at the sections about “Academic Dishonesty,” “Student Code of Conduct and Responsibilities,” and “Disruptive Behaviors.” I will expect students to be aware of these guidelines and to conduct themselves accordingly.

Reasonable and appropriate accommodations will be provided to students with disabilities who present a memo from Student Disability Services (SDS).  

Course Notes:

Sykes CH1 Electronic Structure

Sykes CH2 Energetic and Kinetics

Sykes CH3 Acid Base Chemistry

Sykes CH4 Nucleophilic Substitution

Sykes CH5 Electron Deficient Centers

Sykes CH6 Aromatic Substitution

Sykes CH7 Electrophilic and Nucleophilic Addition to Alkenes

Sykes CH8 Addition to Carbonyl

Sykes CH9 Elimination Reactions

Sykes CH10 Carbanions

Sykes CH11 Free Radical Reactions

Sykes CH12 Pericyclic Reactions

Sykes CH13 Linear Free Energy Relationships