Chemistry 331 is given in two very different formats:
  1. Chemistry 331 is the traditional lecture course that meets 3 times per week with an instructor during the Spring semester each year.

  2. Chemistry 331W, a web-based course, is offered in the Fall semester. Lectures and quizzes are on the Internet.

Chemistry 331W is a web-based course for students interested in the biological aspects of organic chemistry. Many students complete this course to prepare for MCAT and chemistry or biochemistry GRE examinations. Graduate students outside the Department of Chemistry may take this course for 3/4 unit of graduate credit. One semester of introductory organic chemistry (such as Chemistry 231 or 236) is the prerequisite. Because the course is web-based, students must have access to a computer with Internet access and browser software (such as Netscape 3.0).

The course consists of 39 lectures and supplementary material on topics ranging from the basic structure and bonding of organic compounds through the organic chemistry of metabolism and biopolymers. Spectroscopy, synthesis, and mechanism in organic chemistry are important aspects of this course.

For each lecture, there is a reading assignment (CD or textbook) and a series of self-testing problems.

After you complete 3 lectures, you will take a multiple choice quiz on the web. For most quizzes, you can see your graded quiz immediately and learn why any any of your answers were incorrect. You must get at least 60% of the questions right on one quiz. You may re-take the quizzes up to four times. The grade will be the average of all scores for that quiz.

If you need help, you can get it on the WebBoard Conference. This is staffed by graduate teaching assistants at least 20 hours per week. You will always have a response within a day of your questions (usually sooner than that). You can also come to one of our office hours. Times for these will be announced in the Fall.

There are 4 traditional hour examinations over the course of the semester. Each is cumulative and will include questions on the synthesis of organic molecules, mechanisms of reaction, spectroscopy, etc. that we have covered up to the exam date. The example problems at the end of each lecture are closely related to the exam problems.

We will have a weekly review session each Wednesday at 7 PM in 100 Noyes lab except when we have an exam scheduled. If you can't attend the review session, you can see it on the web as a RealMedia presentation.


Teaching Assistants:

Keuchan Oh, 333-3509

Michael Weaver, 333-8020

Do Young Kim, telephone

Stephanie Barnes, 333-3509

Online Discussion Sections






2 PM MW1

8 AM DK1

7 PM KO4

5 PM MW7

12 PM DK3

3 PM MW2

9 AM DK2

8 PM KO5

7 PM KO6

1 PM DK4

5 PM MW3

10 AM KO3


8 PM KO7

6 PM DK5

6 PM KO1

12 PM MW4



7 PM DK6

8 PM KO2

2 PM MW5





3 PM MW6




Office Hours

Use the office hour listed below to ask us any questions you have on the lecture material, quizzes, or exams. Make an appointment directly with Professor Shapley if you need to discuss your grade and performance in the class.

Monday, 8 AM
Room A410 CLSL
Monday, 9 AM
Room A410 CLSL
Monday, 2 PM
Room 464 RAL
Monday, 3 PM
Room 464 RAL
Friday, 4 PM
Room 404 CLSL


  1. There are a large number of well-written textbooks in this area on the market. They all cover the major topics of this course, although the order of the topics varies. You may use any standard organic chemistry textbook as a reference.

  2. There is a study guide for the course. Purchase "Organic Chemistry on the Web: Chemistry 331W" (Part 1, lectures 1-20) at the Illini Union Bookstore.

  3. A CD-ROM containing lecture notes and supporting information is available. You can pick one up when you have your picture taken (Thursday, Aug. 24).

  4. You should purchase a simple molecular model kit. These are available at the Illini Union bookstore. It will help you to visualize 3-dimensional structures and stereochemistry.


Assistance in Learning:


There are a total of 555 points possible in this course:
Your grade is based on your percentage of total points.

Chemistry 331 Syllabus

You may cover the 39 lectures in this course at your own pace. The first 8 lectures cover material that you probably covered in your first course in organic chemistry. If you have recently taken Chemistry 231, 236, or a similar course, you can go through this section very quickly and take the first exam.

There are deadlines for each of the lecture quizzes and the hour examinations. You may take any of these before the deadline.

Date Lecture/Quiz
8/23L1: Electron BookKeeping
8/25L2: Chemical bonding
8/28L3: Conformations, Stereochemistry
8/30Quiz 1
8/30L4: Nucleophilic Substitution
9/1L5: Elimination Reactions
9/6L6: Reactions of alcohols
9/8Quiz 2
9/8L7: Reactions of alkenes and alkynes
9/11L8: Spectroscopy, Symmetry, Nuclear spin
9/13Exam 1
9/15L9: 13C{1H} NMR spectroscopy
9/17Quiz 3
9/18L10: Proton coupled 13C NMR spectroscopy
9/20L11: 1H NMR spectroscopy
9/22L12: Complex spin-spin coupling in 1H NMR
9/24Quiz 4
9/25L13: MRI, IR spectroscopy
9/27L14: Bonding in arenes,polyenes,electronic spectroscopy
9/29L15: Reactions of arenes
10/1Quiz 5
10/2L16: Electrophilic aromatic substitution
10/4L17: Organometallic compounds
10/6L18: Retrosynthetic analysis, Nucleophilic substitution on carboxylic acid derivatives
10/8Quiz 6
10/9L19: Reactions of carboxylic acid derivatives
10/11Exam 2
10/13L20: Ester enolates, Claisen condensations
10/16L21: Mixed Claisen condensations, related C-C bond forming reactions
10/18Quiz 7
10/18L22: Organo-sulfur compounds, Reactions of sulfur compounds
10/20L23: Sulfur-containing amino acids, Molecular recognition
10/23L24: Amines, Synthesis of amines
10/25Quiz 8
10/25L25: Amines as nucleophiles, Amine natural products
10/27L26: E2 reactions of ammonium compounds, Diazonium salts, Nitrosation reactions
10/30L27: Nucleophilic aromatic substitution
11/1Quiz 9
11/1L28: Phenols, Synthesis of phenols
11/3L29: Aspirin, Phenoxide reactions, Oxidation of phenols
11/6L30: Synthesis Problems
11/8Quiz 10
11/8Exam 3
11/10L31: Food, Sugars: conformation and stereochemistry
11/13L32: Reactions of sugars
11/15L33: Polysaccharides
11/17Quiz 11
11/17L34: Glucose metabolism, Fatty acid biosynthesis
11/20L35: Acetate-derived natural products
11/22L36: Amino acids
11/24Quiz 11
11/24L37: Synthesis of peptides
12/4L38: Analysis of Protein structure
12/6Exam 4
12/8L39: Metalloenzymes
11/8Quiz 12