Chemistry 251/253

Organic Chemistry

1999/2000 Syllabus

Instructor- Thomas A. Newton

Class Location- Room 165 Science Building

Class time- M,W,F 10:30-11:20 a.m.

Office- 352 Science

Office Hours- M,W 11:30-12:30; Room 327 Luther Bonney Hall Also by appointment.

Telephone- 780-4316

e-mail- newton@usm.maine.edu

Organic Chemistry, T.W. Graham Solomons and Craig B. Fryhle, 7th ed., John Wiley & Sons, Inc., NY 1999. ISBN 0-471-19095-0

A molecular model kit. The bookstore sells a set from Darling Models. ISBN 0-9648837-1-6

Solutions Manual to accompany Organic Chemistry, 7th ed. by T.W. Graham Solomons and Craig B. Fryhle

Pushing Electrons A Guide for Students of Organic Chemistry, Daniel P. Weeks, 3rd ed., Saunders College Publishing, NY 1997.

1. STRUCTURAL THEORY

a. bonding in organic molecules

1. Lewis structures

2. VSEPR theory

3. Molecular Orbital theory

4. hybridization

b. functional groups

c. molecular structures and molecular shapes

1. stereochemistry

2. optical activity

3. projection formulas

2. REACTIONS OF ORGANIC MOLECULES

a. acid-base chemistry

b. substitution reactions

c. addition reactions

d. elimination reactions

e. reaction mechanisms

f. synthesis of organic molecules

3. SPECTROSCOPY

a. infra-red spectroscopy (IR)

b. nuclear magnetic resonance (NMR)

c. mass spectrometry (MS)

You should also develop a working familiarity with Macintosh computers, including the use of word processing, chemical drawing, chemical modeling, and on-line literature searching programs.

You may have heard that O Chem is a bear. It has taken me a long time to admit it, but I must confess, it is indeed a tough course. Why? There are several reasons. First, the content of the subject is massive. Even though this course focuses on how chemists know what they know, it is impossible to gain that focus without committing a large amount of information to memory. Second, I often tell students that learning organic chemistry is like taking Japanese history....in Japanese; not only do you have to learn the content of the course, you also have to learn the language. Organic chemists don't speak English. They speak Ochemese. Their vocabulary is filled with words like nucleophiles, electrophiles, acylation, alkylation, pericyclic, anti-periplanar, enantiomers, and diastereomers. Such strange words are foreign to most students and they don't sink in the first time you encounter them. Or the second time. Only repeated exposure to the terminology of organic chemistry will enable you to learn the content of the discipline. It's like learning to play basketball: you develop the necessary skills by repeated practice. You can't become a good ball player, or a good student of organic chemistry, by talking about it. You have to do it. Then you have to do it again, and again. That's the way it is.

If Organic Chemistry requires more effort than other courses, it also offers a greater return on your investment. According to the Swiss psychologist Jean Piaget, the two most advanced levels of intellectual development are the concrete operational and the formal operational stages. In chemistry, an individual who is performing at the concrete operational level is able to solve problems similar to examples that have been discussed in class or assigned as homework. They are not, however, able to use their knowledge in an abstract way. A person who has progressed to the formal operational stage can apply their knowledge to problems they have not encountered before. They can think in abstract terms and solve theoretical problems. An individual advances from the concrete operational to the formal operational stage by practice. This is where Organic Chemistry can offer you a greater return on your investment: if you practice enough, you can become formal operational in this discipline. You will be able to solve problems no one else has solved. You will be able to think independently. Nothing is more satisfying than the sense of personal achievement that attends reaching this level of educational sophistication. In pragmatic terms, if you become formal operational in this course, you will get an A. If you become concrete operational, you will earn a C. Which brings me to

Evaluation and Grading-

There will be 12 30-question on-line homework assignments. Each assignment is worth 30 points. In addition, there will be a 70-question comprehensive final examination written by the American Chemical Society. The due dates for each assignment are listed in the following table:

The maximum point total for assignments 1-12 and your final exam is 430 points. I will determine your letter grade using the following point distribution:

less than 252 = F

252-280 = D; 281-293 = D+

294-307 = C-; 308-322 = C; 323-335 = C+

336-349 = B-; 350-364 = B; 365-377 = B+

378-391 = A-; 392-430 = A

Attendance- I do not take attendance. Your presence in class is optional.

Late Homework Assignments- I will not accept late assignments for any reason!

Withdrawl- If you drop this course on or before March 20, you will receive a W. This grade will remain on your transcript. If you withdraw from the course after that date, you will receive a W, which will normally be converted to an F at the end of the semester. Students who do not submit their final exam will receive an I. They must make arrangements with the instructor before the final exam to take the test as soon as possible. A complete description of the University's academic policies is available in the Undergraduate Catalog.

Academic Honesty- In 1995 USM adopted a new Student Academic Integrity Policy. In part that policy reads "The academic community of the University of Southern Maine recognizes that adherence to high principles of academic integrity is vital to the academic function of the University. Academic ingegrity is based upon honesty. All students of the University are expected to be honest in their academic endeavors. All academic work should be performed in a manner which will provide an honest reflection of the knowledge and abilities of each student. Any breach of academic honesty should be regarded as a serious offense by all members of the academic community." A pamphlet entitled USM Student Guide to Academic Integrity highlights key features of the Student Academic Integrity Policy. The pamphlet and the complete policy are available from the Office of Student Judicial Affairs, 125 Upton Hall, Gorham Campus at 780-5242.

Individual work- Honesty is a personal issue. In my view, academic dishonesty is the antithesis of higher education. I do not condone it. However, I am a teacher, not a policeman. I leave you on your honor not to cheat.

Group work- There may be instances in this course where you are expected to work in groups. While I strongly encourage such collaboration, the work that you submit as a result of it must be your own. For example, while it is permissible for one of your peers to show you how to create a structure using a chemical drawing program, you are not allowed to copy and paste that structure into your assignment.

Homework- The on-line assignments listed in the Topics are intended to help you develop the operational skills I mentioned earlier. I view them as a minimum. In addition to them you should do problems in your text on a daily basis. If you have difficulty solving the problems, then you should discuss them with me and/or do additional exercises. Many students rely on the Student Solutions Manual that accompanies the primary text in this course. Be aware that these manuals are generally rife with errors. I strongly recommend that you work in small groups when you do homework. Discussions between 3 or 4 students are generally profitable for everyone concerned.

Academic Assistance- The Chemistry Department as well as the University offer a number of support services for students:

Student tutors are generally available at no cost to the student. Contact Rhonda Shaffer at 4232 for a list of possible tutors.

The Office of Academic Support for Students with Disabilities provides assistance to students who have learning disabilities. Call 4706.

The Office of Learning Assistance provides workshops to help students with Time Management, Note Taking, and Test Taking. Call 4228 for a schedule.

The Learning Center offers free tutoring in writing, math, and word processing. Call 4228.

Study groups can be an effective way to learn. Regular meetings with 2-3 other students offer each participant an opportunity to learn.

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