Kirk McMichael's Organic Chemistry Pages from Washington State University hosted by
California State University, Dominguez Hills

Material for a One Term Survey Course

Laboratory Home Page: <> includes the schedule for the laboratory and links to directions for each experiment.

  Texts: William H. Brown, "Introduction to Organic Chemistry, 2nd Ed." Saunders (Required)
Benson, Iverson and Iverson, "Student Study Guide and Problems", 2nd Ed. Saunders (Optional)

Typical Schedule:
Date Topic Study (Chapter.Section) Read(Ch) Do Problems:
Jan 10 Carbonyl Group: Notation, Structure, Bonding 11.1; 1.1-4; 3.2 11, 1 1.1-8, 23, 25-26, 29-30, 34-35, 38-40; 3.1-2, 13, 15-16; 11.14
Jan 12 Functional Groups, Hybridization, Naming 11.1-2; 1.6-7; 3.3-5 11, 3 1.12-14, 47-49, 52-56; 3.3-5, 12-18, 20-21; 11.1-3, 11.16-17
Jan 14 Additions: Mechanism, Electrophile, Nucleophile 11.4; 2.5; 6.2-3; 7.2  11, 2 2.4, 20; 6.8-10
Jan 19 Acetal Formation, Mechanism, Resonance 11.6; 1.5 11 1,10-11, 44-46; 11.6, 26-29
Jan 21 Nitrogen Nucleophiles: Imine Formation 11.7, 11.10C; 2.2 11, 3 2.9-12; 11.7, 31-32
Jan 24 Addition of Organometallics, Grignard 11.5 11 11,4-5, 18, 20a,c-g, 21-23
Jan 26 Oxidation & Reduction, alpha-C-H acidity 11.8-10; 14.1,1.4 11, 14 11.8-10, 38-39, 41a,d,f, 42d
Jan 28 Enolates, Aldol Condensation, Synthesis 14.1-2 14 14.1-7, 11-13, 15, 18-20
Jan 31 Carboxylic Acid Derivatives: Interconversion 12.6-7, 13.1-8 12, 13 12.4-5, 30, 33; 13.1-5, 8-9,13, 16-18, 20-22, 26-28, 32-33
Feb 2 Carboxylic Acid Derivatives - Alpha Carbon Reactions 12.8; 14.3-4 12, 14 12.6, 35; 14.8-10, 25-31, 34
Feb 4 Fats, Fatty Acids, Detergents 17.1-2 12, 17 17.1, 3, 11-12, 14
Feb 7 Review      
Feb 9 Exam 1      
Feb 11 Carboxylic Acids 12.1-8 12 12.1-6, 8-9, 17a-b,d,20, 22, 27, 29-34
Feb 14 Alcohols 8.1-4 8 8.1-3, 6-9, 12-14, 27-31, 33, 37a-e, 41a-b, 42d; 11.40, 42b-c
Feb 16 Ethers, Epoxides, Thiols 8.5-8 8 8.4-5, 10-11
Feb 18 Chirality, Three Dimensional Structure 4.1-2, 6-7 4, 3 4.1, 8-10, 12-16, 18-20
Feb 21 R/S Naming, Two or More Stereogenic Centers 4.3-5,8; 3.6A 4, 3 3.6, 22-23; 4.2-7, 17, 21-27, 32; 11.16b,d, 33, 37
Feb 23 Carbohydrates: Monosaccharides 16.1-6, 11.6. 3.6B 16 3.7-8, 31; 16.1-6, 9-10, 14-23, 26
Feb 25 Glycosides, Disaccharides, Polysaccharides 16.7-8 16 16.7, 30, 33-37
Feb 28 Review      
Mar 1 Exam 2      
Mar 3 Amines: Structure and Synthesis 10.1-3, 11.10C, 13.8B  10 10.1-3, 8-10, 12-13; 11.11, 31-32; 13.6, 7c, 29c, 39
Mar 6 Amines: Reactions 10.4-5, 11.7, 13.5 10 10.4-7, 16-20; 11.7, 11, 31-32, 42d; 13.4, 25, 26, 27d, 30a
Mar 8 Amino Acids and Peptides 18.1-2 18 18.1-3, 8-17, 22-26, 28, 32-33
Mar 10 Proteins 18.3-5 18 18.4-7, 37-40, 43, 45, 47
Mar 13-17 Spring Break 19.1-5 19 19.1-6, 9-11, 16-18, 21-25, 29-30, 32,39, 41
Mar 20 Nucleic Acids 7.1-5 7 7.1-3, 7-8, 14-24, 26-28
Mar 22 Nucleophilic Substitution, SN2, SN1 7.6-7, 5.2C 7 7.4-5, 29-32
Mar 24 Elimination, E2, E1      
Mar 27 Review      
Mar 29 Exam 3 5.1-4, 7.6-7 5 5.1-9, 11-13, 15-18, 21, 23, 25
Mar 31 Alkenes & Alkyne Structure 6.1-6 6 6.1-7, 11-19, 22-23, 29-31, 33-37; 8.43; 11.13d,h, 41a-g,h
Apr 3 Electrophilic Additions 15.1-5 15 15.1-10, 13-14
Apr 5 Polymers 20.1-7 20 20.1-6, 8, 11, 13-16, 18-21
Apr 7 Metabolic Organic Reactions 9.1-3 9 9.1, 9-12
Apr 10 Aromatic Compounds 9.6-9 9 9.4-8, 19-29
Apr 12 Electrophilic Substitution
Apr 14 Side Chain Oxidations, Phenols, Arylamines  9.4-5; 10.1 9, 10  9.2-3, 14-18, 36-39 
Apr 17 Review      
Apr 19 Exam 4      
Apr 21 Radical Reactions      
Apr. 24 Review
Apr 26,28 Review      
May 5 Final Exam, 7-10 am      

Study Grades Problems
Study: Learning organic chemistry requires you to develop and exploit disciplined study habits. It cannot be effectively mastered by all-nighters before exams. You must study regularly and intensively. Organic chemistry is both detailed and extensive. Study each chapter before as well as after it is discussed in lecture. Keep up with the problems. Use the time before exams for review, not for cramming. Organic chemistry is relentlessly cumulative and intensely interrelated. Once you fall behind, catching up is very difficult. Your disciplined effort will be repaid by the satisfaction that comes with mastering complex material, and that will result in a grade to be proud of.

You will find that much detailed information must be remembered. This is easier and more effective if the details are connected by a framework of general ideas such as mechanistic patterns and functional group similarities. Try to connect each new bit of information to what you already know. Look for analogies between the new material and the old. Solidify your knowledge and make it useful by doing problems?lots of problems. You must understand the general ideas thoroughly and use them regularly in grasping the details in order to comprehend the material.

Grades: Exams will be given on the dates indicated. Grading will be based on 100 points for each of the four hour exams, 200 points for the final (2 - 3 hours), and 200 points for the laboratory. The majority of the problems on exams will be taken directly from problems in the text. Since organic chemistry is so interrelated, it often happens that students will understand material better in the context of reviewing for the final than was they did when the material was first presented. For this reason, the final is also used as a make-up exam. This is done by calculating a separate percentage score over those questions on the final which relate to a particular mid-term. If that score is higher than the mid-term score, it will replace the midterm score in the grade calculation. No separate make-up exams will be given. Incompletes are reserved for cases where unforeseeable problems arise from circumstances beyond the student's control.

Problems: You should do all exercises found in body of each chapter or section as you study. These exercises are designed to give you practice in using the chemistry you have just studied. They are important both as practice and as a self-test of your grasp of the material. It is also very important to do the problems at the end of the chapter. This will improve the speed and understanding with which you tackle the exam questions. You will also find out how well you grasp the material in the chapter and where you need intensive review.

In doing the problems, avoid checking the answers in the Study Guide before you have completed the solution. If you need more background, check the text and your notes for similar chemistry, and apply those principles. If your answer is not like the one in the Study Guide, analyze the answer in the Study Guide to understand the ideas used and how they are applied. Often, there are several satisfactory approaches, so if you have a different approach than that used in the Study Guide, and you have checked your solution, verify it with me.

Practice Exams: Copies of exams from Spring 1999 are posted on the Web (Practice Exams). Please note that we are using a different text than was used in the Spring. After each hour exam, a key and an audio tape discussing each problem and its solution will be placed in SLIC.

Computer Exercises: Further opportunities to practice are afforded by the computer problems found on the Gateway Computers in Fulmer 401 and at SLIC. Last year, students who used the computer exercises had an exam average about 10 points higher than those who didn't. Computer usage at SLIC is subject to a $10.00 per semester fee this year.

Frequently Asked Questions ? and Their Answers:

1. Is this going to be on the exam?
Maybe: I want you to learn more than four mid-terms and a final can cover. One way to encourage that is to expect you to come to the exam prepared to handle more material than the exam contains. That won't happen if I answer the question directly. Remember, you're taking the course because it's important to your professional development, not just to pass the exams.
2. Will the course be graded on the curve?
If you mean that some predetermined proportion of the class will get A's, and some other predetermined portion will get F's, the answer is no. If the whole class does well, there will be many A's; if the whole class does poorly, there will be many F's. Grade assignments corresponding to specific ranges of exam scores will be announced after every mid-term. These will be roughly like the following:



A > 88, A- > 82, B+ > 78, B > 74, B- > 70, C+ > 66, C > 56, C- > 50, D > 40, F < 41.

These breaks may shift slightly when significant gaps in the grade plot occur.

3. Do I really have to study two hours a day?
Not if you are a genius, and not if you don't care about learning organic chemistry and/or the grade which reflects that learning. If you do care, but you think you might not be a genius, then study regularly, do problems, and--most important of all--think about organic chemistry. That will lead to a solid understanding, a sturdy foundation for the next courses you are to take, a good platform for further development in your professional field, and incidentally, a good grade.
4. Why is organic chemistry so hard?
I'm not sure it's hard. It is demanding, though. There is a lot of detail to master, much like the vocabulary in a new language which is best grasped by relating new words to ones you already know. That's why we expect to learn about a new functional group by relating its behavior to that of a similar functional group we already know about. This rewards the student who looks for connections between what is new and what is already known. It makes things very difficult for the student who learns material in isolated chunks so as to pass an exam and then forgets it the next day. Keep asking yourself the questions, "What do I know that resembles this new stuff? What is this like? What are the important differences?" It's more than just memorization, and that really makes it more interesting.
5. Do we really have to know this stuff?
If you mean, "Can I live a happy and successful life without knowing organic chemistry," the answer is yes. If you mean, "Can I get a good grade without knowing this stuff," the answer is no. If you mean, "Why does the curriculum for my degree include organic chemistry," you'd do better to ask your adviser.
6. What should I do if I'm confused?
Seek help. See me or the TA's (office hours above). Use the review suggestions for each chapter. Use the computer materials in Fulmer 401 or at SLIC. Even try the index of the text! But do contact me. I'd prefer to work with you early in the semester to help clear up problems then, rather than to find out later on that there isn't enough time left for you to recover. If the office hours don't work for you, let's make an appointment that works for both of us.