Chem 32.Intro/97

Note: The office hour schedule might change during the semester! The most recent regular schedule will always be posted on the web and on the bulletin board immediately to the right of my office door (Science Center 292). Idiosyncratic changes will be announced on BlackBoard and also posted on the schedule by my office door.

Class Meeting Time and Place:

MWF 9:30-10:20 Science Center 101 (lecture)
W 1:15-4:45 Science Center 161 (seminar)

Faculty and Staff Associated with Course:

Paul Rablen (professor), Science Center 292, x8341, email prablen1.

Robert Paley (professor), Science Center 182, x8525, email rpaley1.

Maria Newport (lecturer), Science Center 167, x8526, email mnewpor1.

Donna Halley (laboratory instructor), Science Center 165, x8532, e-mail dhalley1.

Lori Sonntag (laboratory instructor), Science Center 267, x8602, e-mail lsonnta1.

Texts and Materials:

Jones, M., Jr., Organic Chemistry, 3rd Edition, W. W. Norton, 2004 (required).

Jones, M., Jr., and Gingrich, H., Study Guide/ Solutions manual for Organic Chemistry (required).

Zubrick, J. W. The Organic Chem Lab Survival Manual, 7th Edition, John Wiley & Sons, 2007 (strongly recommended).

Chemistry 22 Lab Manual -- available through the Department of Chemistry & Biochemistry (required).

You also must have a hard-covered, permanently bound notebook, about 8" x 10".

A few copies of the Zubrick lab text will be kept on reserve in Cornell Library. The syllabus, sample exams from previous years, and other helpful materials will be available in electronic form through BlackBoard. The text and study guide are the same ones that will be used in Chemistry 32 next semester. Molecular models are frequently helpful, and can be purchased from a student in a previous year's class, or ordered through the internet.

General Format for Lecture:

The lecture section of this class will follow traditional lecture course format. The most essential material of the course will be presented in class, although I will also assume that student read the assigned sections of the textbook. Also, I intend to write “thought questions” on the blackboard before the start of class on most days. You should think about these questions as you arrive in class and settle down. In fact, you might even want to arrive a few minutes early so that you have more time to think about the questions. These questions will serve to get your mind “warmed up,” and also will help you gauge your understanding of the material. The answer to the “thought question” will generally appear at some point in the lecture for that day (often at the very beginning).

The text will present the material from a slightly different perspective, and in addition will also serve as a reference.

General Format for Seminar:

The seminar section of this class will follow a participatory format, in which students play an active and engaged role, and in which lecturing is held to a minimum. Students will be responsible for carefully reading the assigned material in the textbook before class. During class, ample opportunity will be provided for questions. Once in a while, the instructor will also give “mini-lectures” 15-30 minutes in length about key concepts that are difficult to learn just from the textbook, or that don’t appear in the textbook. Considerable classroom time (50% of it or more) will be devoted to working on problems, sometimes as an entire class and sometimes in small groups (3-4 students per group).

Learning Goals:

There are many goals for this course, and it is not possible to compose an exhaustive list. Any list will inevitably leave out some goals -- even some important ones! It is in the nature of liberal arts education that we aren’t always fully aware of all the ways in which we are teaching, learning, and developing. That being said, below is a list of some of the most important and immediate learning goals that I have for students who take this course. This knowledge and these abilities are what I hope students will take with them when they’ve finished the course.

1. Knowledge and understanding of the fundamental principles, methods, structures, and reactions of organic chemistry; mastery of the “canonical knowledge” of the field.

2. An understanding of organic structure: the ability to draw organic compounds, comprehend their three-dimensional geometry, and recognize their constituent functional groups; and the ability to use this knowledge to make predictions about chemical properties and reactivity.

3. The ability to write reaction mechanisms, using the proper symbolic “grammar;” and the capacity to think mechanistically. This goal includes both remembering and understanding the exact mechanisms for the most common and fundamental reactions, and also the ability to make reasonable predictions for new situations.

4. The ability to design simple syntheses: that is, the capacity to string together known reactions in a carefully planned sequence so as to generate a desired chemical structure from available starting materials.

5. The ability to draw conclusions about the structures of organic compounds from their spectroscopic properties, and also to some extent from their chemical properties.

6. The ability to communicate about organic chemistry, both in words and in the symbolic “language” of structure and mechanism used by organic chemists.

7. The ability to make reasonable predictions of the behavior of organic compounds, or to give reasonable explanations for observed behaviors, by integrating and generalizing from the “canonical knowledge” of the field.

8. The ability to carry out with competence and safety the most common and fundamental procedures used in an organic chemistry laboratory.

9. An appreciation for how “organic chemistry on paper” actually corresponds to “real chemistry” in the laboratory.

Laboratory:

The laboratory is an integral and required part of this course, and is described in detail elsewhere. Laboratories begin on Monday, January 19 (i.e., the first week of classes). Laboratory sessions take place 1:15-4:30 PM Monday through Friday and 8:00-11:15 AM Thursday, and will meet in the organic laboratory (room 174, on the first floor of the Science Center). Lab lectures will often precede the actual experiments, and take place in Science Center 181. The experiments are designed to be carried out in approximately 3.0-3.5 hours, but students need to work efficiently and be properly prepared to finish on time! The laboratory manual gives more detailed information about the required preparation for each experiment.

Attendance at labs is required, and students must come to the laboratory session to which they are assigned. Arbitrary switching of lab days is not permitted. Absences occasioned by illness or other legitimate reasons are excused only when followed by a memo from a doctor or the Dean's Office explaining the absence. Attendance at or participation in athletic events or other extracurricular activities is not considered a legitimate reason for missing regularly scheduled laboratory sessions. However, with sufficient advance planning, it is sometimes possible to make arrangements for a student to come to lab on a different day in order to accommodate athletic contests. If you foresee any difficulties about being able to attend the lab session to which you have been assigned, see one of the instructors as soon as possible.

Dr. Newport holds primary responsibility for administering the laboratory portion of the class.

Problem Sets:

Problems from the textbook will be assigned on a regular basis, as will supplementary “handout” problem sets written by the instructor. Doing (and understanding!) problems is necessary for learning organic chemistry. It is essential that you complete the problem sets in a timely fashion. Students having trouble with the course as a result of neglecting to complete the assigned problems will get little or no sympathy from the instructor!

Students are encouraged to work together on problem sets. However, it is essential that each student actively contributes to any collaborative effort, and that nobody merely "catches a free ride." This precaution is absolutely necessary to ensure that everybody actually learns the material. The best arrangement might be for each student to work on the problems by herself or himself at first, and only to consult with other students or with the instructor after having made a serious individual effort.

It is important that you check your answers against the solutions manual and the posted keys to make sure you have understood the material. However, do not use the solutions manual prematurely! It is all too easy to persuade yourself that you understand a problem well enough to do it on your own when in fact you don't. So, don't look at the solutions manual until after you have made your best attempt at answering the problems on your own.

In order to emphasize the importance of doing the problems, homework assignments will be collected. Problems assigned from the textbook will be checked primarily for completeness, while the handout problems will be checked in somewhat more detail. Collectively, the problem sets will carry a weighting equivalent to a single exam in the final grading for the course.

Please note: it is still your responsibility to check your answers and to make sure you understand the material. However, if you include a note asking the grader specifically to check a particular question, she or he will generally be happy to do so.

Hint: If you get stuck doing the assigned problems, don’t just give up, and also don’t spend hours banging your head against a wall; take a step back and do some of the easier problems from the chapter (lower-numbered ones which were not assigned) first!! Doing these problems will help you develop the skills you need in order to tackle successfully the more difficult, assigned problems. Please also note that the textbook includes many problems that are embedded in the text of the chapters. These problems comprise an integral part of the text, and you should generally do all of them (unless otherwise noted), even if only a small fraction of them are listed as “assigned” (i.e., to be collected for grading).

One of the best ways to study for exams is to solve still more problems, or to do over again the problems (especially the toughest ones) you did earlier. In addition to the assigned problems (which will be collected), other problems from the book will be designated as recommended, and still others as optional. You can use these problems for additional practice.

However, It is also important to recognize that quantity does not substitute for quality. Doing large numbers of problems in a superficial manner, without insight or reflection, will not help you as much as doing a smaller number of problems with care, inquisitiveness, and attention to detail.

As an added incentive to do homework, each exam will contain at least one question taken directly from either the assigned or recommended problems.

Assignments and Due Dates:

Homework assignments (including reading) and the corresponding due dates are posted in the “Assignments” section of BlackBoard.

Grading:

Three components will contribute in an equal fashion to the final semester grade: lab (30%), term-time exams (30%), and the final exam (30%). In addition, the problem sets will contribute 10%. There will be three term-time exams. There will be no make-up exams. Two quizzes will also be given; the scores on these quizzes will not count toward your final course grade unless they improve it (details below).

The following calculation will also apply: if a student’s course grade at the end of the semester comes out below B-, then a second grade calculation will be carried out in which the weighting is 25% for the term-time exams, 25% for the final exam, 35% for the lab, and 15% for the homework. The student will receive whichever grade is higher, the one from the original calculation, or the one with the revised weightings, except that the revised weightings cannot raise the grade higher than B-.

Exams:

There will be three exams during the semester, as well as a cumulative final exam at a time scheduled by the registrar. The three term-time exams will be administered in the morning, from 8:20-10:20 PM, on Wednesday, February 18; Wednesday, March 25; and Monday, April 27. The reason for scheduling the exams outside of class is to allow more time than would otherwise be possible, so that nobody feels rushed. The longer time period fosters a much more relaxed, lower-stress test-taking environment. Both sections (lecture and seminar) will take the same exams. I recognize that 8:20 AM is probably not most students’ favorite time to take a test, but the morning time period causes fewer conflicts than an evening time period would.

If a student has an unavoidable conflict with one or more of these exam dates, special arrangements can be made, but advance notice must be given -- at the very least a week in advance, but preferably as soon as the conflict is recognized (e.g., the first week of classes!).

Quizzes:

There will be two very short quizzes during the semester, on Friday, February 6, and on Wednesday, March 4 (Wednesday, February 4 and Wednesday, March 4 for the first-year seminar). Each will take 15 minutes, and be administered at the start of class. The quizzes serve the intended purpose of providing you with feedback, in advance of the exams, about what is expected of you in terms of drawing three-dimensional chemical structures and writing reaction mechanisms. Accordingly, the quizzes will be scored, but the grades will not count. However, the two quizzes together can substitute for one-half of your lowest term-time exam score, if that turns out to help your grade.

Term-Time Exam Dates:
Wednesday, February 18

Wednesday, March 25

Monday, April 27

Exams will be at 8:20-10:20 AM on these days.

Term-Time Quiz Dates:
Friday, February 6 (Wednesday, February 4 for seminar section)

Wednesday, March 4

Quizzes will take place during the first 20 minutes of class on these days.

Approximate Schedule of Reading assignments:

Week                                   Chapters                     Topics

Jan. 19 – Jan. 23               1, 2                                Bonding, Hybridization, & MO Theory
Jan. 26 – Jan. 30               2, 3                                Alkanes, Isomers, and Conformations
Feb. 2 – Feb. 6                 3, 4                                Alkenes & Alkynes; Stereochemistry
Feb. 9 – Feb. 13               4, 5                                Stereochemistry; Rings
Feb. 16 – Feb. 20             6, 7                                Alcohols, Amines, Ethers, etc.
Feb. 23 – Feb. 27             7                                     Substitution & Elimination
Mar. 2 – Mar. 6                   7, 8                                Thermodynamics & Kinetics
Mar. 9 – Mar. 13                SPRING BREAK
Mar. 16 – Mar. 20              9                                     Addition Reactions of Alkenes
Mar. 23 – Mar. 27              10, 11                            Alkenes and Alkynes; Radical Reactions
Mar. 30 – Apr. 3                11, 15                            Radical Reactions; Spectroscopy
Apr. 6 – Apr. 10                15                                  Spectroscopy
Apr. 13 – Apr. 17              15                                  Spectroscopy
Apr. 20 – Apr. 24              12                                  Dienes and Conjugation
Apr. 27 – May 1                13                                  Aromaticity