Chemistry C3443 Organic Chemistry I
Fall 2003 Section 2

http://www.columbia.edu/itc/chemistry/c3443_sec2

Instructors
Professor Virginia Cornish
office location: 418 Havemeyer
office hours: F 4:00-6:00 p.m.
email: [email protected]

Meghann Brown
office location: 343 Havemeyer
office hours: TBA
email: [email protected]

Carmen Garcia-Irizarri
office location: 343 Havemeyer
office hours: TBA
email: [email protected]

Pamela Peralta-Yahya
office location: 343 Havemeyer
office hours: TBA
email: [email protected]

Undergraduate Chemistry Office
For general administrative questions (where your recitation is, you have a conflict with the time of the final exam, you were not in class to pick-up your exam, etc.), see Ms. Socorro Lugo or Ms. Daisy Melendez in 318 Havemeyer.

Lecture and Recitation Sections
Lecture: MW 1:00-2:15pm 428 Pupin
You are responsible for material covered in the lecture. The textbook should be used as a reference book and a source of practice questions. You are not responsible for additional material covered in the textbook unless explicitly stated in class. Working the problems in the book, however, probably is the best way to learn the material.

Recitation Sections: time and location TBA.
Recitation times and locations can be accessed via the course web site (above). Register for recitation sections on the web as usual. Note that registration is on a first-come, first-serve basis. Recitations are taught by the teaching assistants. Recitations begin the second week of classes. Quizzes (starting the third week of classes) will be given on a weekly basis in the recitation sections, and your quiz average is factored into your final grade.

Course Materials
Textbooks (required):
(1) J. McMurry, "Organic Chemistry", 5th Edition, Brooks/Cole, Pacific Grove, CA, 2000.

Textbooks (supplemental):
(2) D. P. Weeks, “Pushing Electrons”, 3rd Edition, Harcourt & Brace, Orlando, FL, 1998.
(3) A. Miller and P. H. Solomon, “Writing Reaction Mechanisms in Organic Chemistry,” 2nd Edition, Academic Press, London, 2000.
(4) A. Streitwieser, Jr. and C. H. Heathcock, "Introduction to Organic Chemistry", 4th Edition.
(5) M. Jones, “Organic Chemistry”, 2nd Edition, W. W. Norton & Company, New York, 2000.
(6) J. March, "Advanced Organic Chemistry", 5th Edition.
(7) F. A. Carey and R. J. Sundberg, "Advanced Organic Chemistry", Part A and B, 4th Edition.

Molecular Models (recommended):
(8) Computer molecular models: ChemOffice (available at the Columbia Book Store bundled with copies of the required texts in both PC or Mac versions).
(9) Ball and stick molecular models: the Prentice Hall “Molecular Model Set for Organic Chemistry”, available at the bookstore, is recommended.

Reading and homework will be assigned from the McMurry textbook. Note that Brooks/Cole has several supplementary companion texts to the McMurry textbook as well as supplementary material on their web site. Streitweiser & Heathcock and Jones are also excellent organic chemistry textbooks. In particular, Jones has an in-depth treatment of atomic and molecular orbital theory. The Weeks and Miller textbooks have lots of electron-pushing problems—a common area of difficulty, with more introductory problems in the Weeks textbook. March and Carey & Sundberg are more advanced textbooks if you are particularly interested in a given topic. The supplemental text can all be found on reserve in the Chemistry Library (4th floor Chandler). Molecular Model Sets are highly recommended. They help with the visualization of stereochemistry and reaction geometry.

Homework
Homework will be assigned approximately once a week. Homework will be announced in class and posted on the web. The teaching assistants will go over selected homework problems in the recitation sections. Each exam will have at least one problem taken directly from the homework.

Examinations
There will be weekly quizzes, 4 midterm examinations, and a final examination. The quizzes will be held in the recitation sessions. The midterm exams will be held during class on: 29 September, 20 October, 10 November, 1 December. The midterm exams will emphasize the material taught during the preceding month but will be cumulative. All exams must be taken in blue or black pen (no pencil), and calculators are not allowed during the exams. The time and location of the final exam will be determined by the registrar.

This course is graded on a curve. The letter grade assigned to the mean, however, will reflect the classes’ overall performance. Grades will be calculated as quiz average 5% and midterm and final average 95%. The quiz average will be calculated as the average of the top 75% quiz grades. The midterm and final average will be calculated as an average of the midterm and final exams, with each midterm counting as 1 unit, the final counting as 3 units, and the 2 lowest units dropped. There is a generous drop policy, but no make-up exams or quizzes.

Regrades should be submitted to the Undergraduate Chemistry Office in 318 Havemeyer. Regrades will be accepted up until 1 week after the answer key is posted. Any exam that is submitted for a regrade will be regraded in full by Professor Cornish.

Approximate Schedule

Week of Topics

Sep 1 and 8 Emphasis: Nomenclature, 2-Dimensional Representation
Chapters 1-3

Sep 15 and 22 Emphasis: Atomic Orbitals, Molecular Orbitals, 3-D Representation
Chapters 1-4

Midterm #1: Monday, 29 Sepember

Sep 29 Emphasis: Acidity/Basicity and Kinetics/Thermodynamics
Chapters: 2, 5

Oct 6 and 13 Emphasis: Mechanism, Substitution Reactions, Stereochemistry
Chapters 5, 9, 11

Midterm #2: Monday, 20 October

Oct 20 and 27 Emphasis: Alkenes and Alkynes
Chapters 6-8

Nov 3 Emphasis: Alkyl Halides
Chapter 10

Midterm #3: Monday, 10 November

Nov 10 Emphasis: Structure Determination
Chapters 12-13

Nov 17 and 24 Emphasis: Conjugated p-Systems
Chapters 14-15

Midterm #4: Monday, 1 December

Dec 1 Review

Dec 8 Review

Final Exam: TBA