PLU
Organic Chemistry II 

Lecture 

Chemistry 332

Reactants in a Diels-Alder Cycloaddition 
Philosophy of Life Course Calendar
Course Materials Organic Study Sheets
Classroom Activities Learning Groups
Homework Use of Computers
Email The Organic Journal Club (TOJC)
CD Resources and Molecular Models Academic Policies and Grading
Organic Tool Kit Organic Home Page
This Course Accompanies
Chem 334 (Organic Chemistry II Laboratory)
Instructor: C. Fryhle, RSC 240, X8314
Lecture: MWF 8:00-9:05 A.M., Ingram 100
Office Hours: MF 9:30-10:30, W 12:30 - 1:30, Th 1:00-2:00
Chem 334 Lab Info Sessions:  M 1:35-2:00, Rieke 224
Internet: fryhle@rainier.chem.plu.edu
WWW http://rainier.chem.plu.edu/fryhle.html

ORGANIC CHEMISTRY

Chemistry 232 Fall 2000

(http://rainier.chem.plu.edu/chemdept/organic.html)
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Philosophy

Life is Organic Chemistry

Chemistry 332 is the second term course in Organic Chemistry. The topics covered in Chemistry 332 build upon fundamental principles and reactions learned during the first term of Organic Chemistry (Chemistry 232). In this course we will discuss the properties of conjugated and aromatic compounds, carbonyl compounds, amines, phenols, and biological molecules such as carbohydrates, lipids, proteins, and nucleic acids. By the end of chemistry 332 you will have a well-rounded appreciation for the scope of organic chemistry. You will have become acquainted with many classic reactions in organic chemistry, a wide range of functional groups, and the essential classes of biomolecules with which living systems are built. Just as for the first term course, it is my hope that the broadening of your acquaintance with organic chemistry this semester will inspire an appreciation for the beauty of chemistry's fundamental role in life processes. There is much to learn, and substantial effort on both of our parts is expected and necessary in this endeavor. All of our efforts are worthwhile, however, as we come to more fully appreciate the wonderful intertwining of chemistry with all of life.

Although it may appear that organic chemistry is the ultimate test of one's ability to simply memorize reactions, this is not so. It is still true in Chemistry 332, as it was in Chemistry 232, that by developing command of a select and relatively small set of rudimentary concepts and reaction types, one can generalize to a large number of other organic reactions. To be sure, there is challenge involved in learning the essential principles, but there is also much beauty and elegance to behold when one sees the interrelationships among these principles and begins to apply them creatively in broader situations.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading
Course Materials:
1) Solomons, T.W.G., Fryhle, C. B. Organic Chemistry, 7th ed., John Wiley and Sons, Inc., New York, 2000.
2) Solomons, T.W.G., Fryhle, C.B., Johnson, R.G. Study Guide to Accompany Organic Chemistry, John Wiley and Sons, Inc., New York, 2000.
3) Organic Chemistry Study Sheets, C. B. Fryhle, 1995, 2000.
4) Highly Recommended: Molecular Model Kit
5) Email access (free to PLU students).
6) Personal computer.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

Fall 2000 Calendar for ORGANIC CHEMISTRY II (Chem 332)

Monday  Wednesday  Friday
W Written Exercise 
D Lecture/Discussion/Requests 
LG Learning Group Presentations
September 11
Introduction/13
September 13
13-W
September 15
13-D
September 18
13-LG
September 20
14-W
September 22
14-D
September 25
14-LG
September 27
15-W
September 29
15-D
October 2
15-LG
October 4
Library Lecture
October 6
Exam I
October 9
16-W
October 11
16-D
October 13
16-LG
October 16
17-W
October 18
17-D
October 20
17-LG
October 23
18-W
October 25
18-D
October 27
Mid-Semester Break
October 30
18-LG
November 1
19-D
November 3
Review
November 6
Exam 2
November 8
19-W
November 10
19-LG
November 13
20-W
November 15
20-D
November 17
20-LG
November 20
21-W
November 22
21-D
November 24
Thanksgiving Holiday
November 27
21-LG
November 29
22-W
December 1
22-D
December 4
22-LG
December 6
Exam 3
December 8
23-W
December 11
23-LG
December 13
24-W
December 15
24-LG
December 18
Final Exam 
(ACS Stand.)

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

Classroom Activities

We will spend roughly three class days on each chapter. During these days, our time will revolve around three principle activities, which are described in detail below and scheduled on the calendar.

What YOU Need To Do

I cannot emphasize enough the importance of regular class attendance and diligent study habits. You will find that the flow of material is constant and substantial. I say this not to alarm you, but to help you develop the best study habits that you can, as soon as you can.  Without daily reading, studying, and working of problems, together with attendance at every class you will quickly find yourself too far behind to ever catch up. If you develop good habits, then you will be able to handle the flow of information and concepts. You simply must do some organic chemistry every day.

As you read the text, you should take notes on what you are reading. Writing is one of the most important tools for learning. You must work the problems, too, both as you read the text and between reading periods and classes. Many people also find it useful to create their own reaction summaries.

The concepts in organic chemistry build as though they were an inverted pyramid. Hardly any concept is ever learned and discarded. Rather, all the ideas presented become incorporated into a foundation for the understanding of later topics. Regular reading, attentive time spent in class, and interaction with peers in your Learning Group (see below) will ensure that you have the absolute best chance to learn all that you can about organic chemistry and do as well as you can. There simply are no shortcuts.

In-Class Written Problems and Discussion

On the first or second day for each chapter I will provide you with a 5-10 minute closed book, in-class exercise to be worked independently about some aspect of that chapter. My assumption is that you will have read the chapter in advance (at least the early sections) and be prepared to work with some basic concepts from that chapter on the quiz. We will evaluate and discuss this assignment immediately afterward, using it as the guide for our discussion that day. The exercise will be worth ten points, with the best ten out of twelve scores of the semester counted toward your point total. The quizzes will generally help your class total, so long as you attend class faithfully and read ahead. There will be no make-up opportunities for these exercises since there will be more opportunities provided than are counted in the total.

Lecture and Discussion on Requested Topics

On the second day for each chapter our class time may be spent on topics that you request in advance. You can forward your questions, problems, topics of interest, etc., to me in advance in person, by email, phone, or on paper. Some topics for lecture may be generated by postings to The Organic Journal Club (TOJC, see below). I will use your input to shape my discussion so that it addresses material about which you have concerns or questions.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading
Learning Group Problems

I have written some problems called Learning Group Problems that appear at the end of each chapter.  These problems are highly integrative.  They draw upon a variety of important concepts from the specific chapter under study, and frequently they utilize concepts you have studied earlier.  By working the Learning Group Problems (after you study the chapter and do some other problems), the LGPs will help you  use and reinforce your learning of key concepts in organic chemistry.  Furthermore, the Learning Group Problems will frequently highlight some interesting aspect of chemistry or expand upon a Chapter Opening Essay or "The Chemistry of..." box.  I count on everyone to work on the Learning Group Problems in every chapter as a way to cement their understanding of important topics.  Specific groups of students, called Learning Groups, will be responsible for guiding the class through the solution to their two assigned Learning Group Problems.  Each of these will be graded on a 35 point scale.  More information about that follows.

Learning Group Activities

The class will be divided into groups of 4-6 students. Group membership will be determined at random, but once formed there will be elements of design in how the group functions. On the third day of coverage for a given chapter, one of the assigned Learning Groups will present its solution to the Learning Group Problem for that day.  The Learning Group Presentation Schedule is given below. The group's presentation should be about 20 minutes long. A key aspect of the presentation is that it should teach the class about the chemistry in the problem by explaining the rationale and method of the solution.  I will grade part of each group's work solely on the merits of their presentation.  Members of each group will have defined roles that ensure that all members become equally engaged in solving the problem (see below), but all members may participate in the presentation. Even though only two groups (of 12) are assigned to prepare for each given problem, it behooves all persons in the class (i.e. the remaining groups) to work on each Learning Group Problem, since problems similar to the Learning Group Problems will appear in various forms on exams.

Schedule of Preparations by Learning Groups


Chapter 13 14 15 16 17 18 19 20 21 22 23 24
Learning 
Groups 

3
4
5
6
7
8
9
10
11
12
1
2
3
4

6

9
10
11
12
As you can see, I will not be providing lectures for you every day, per se. It will be the text and elements of class discussion that serve as the primary sources of factual material for which you will be responsible. I will assist you by providing appropriate emphasis for chapter sections through Organic Chemistry Study Sheets. You are responsible for reading the text carefully to glean the essential content for the course. In this way, our class time can be comprised of actual working sessions and fruitful discussions about organic chemistry, rather than simple regurgitation of the text.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

Assigned Homework Problems

Implicit in the design of how our classroom time will be spent is the notion that chemistry can only truly be learned by the working of problems. The classroom and reading alone will not suffice. You are responsible for your learning in this class, although I am your guide and mentor. Thus, problems from each chapter will be assigned (but not collected). Problem assignments are given at the bottom of the Study Sheet for each chapter. Solutions to the assigned problems can be found at the back of the text and in the accompanying Study Guide. You must give each problem a good effort before consulting the Study Guide for an answer if you are to learn by the process. You must work problems every day, or else you will not have sufficient time to absorb the material and measure your skills before exams. This is time-tested advice. If you ask, we can take time to discuss some problems in class. It is best for your learning if you give the problems solid effort in advance before asking for help, however. I am, of course, available for your assistance during my scheduled office hours, through email, and frequently during other times as well.

Molecular Models

You will find that working with hand-held molecular models enhances your understanding of organic chemistry immensely.  I strongly recommend that you purchase a molecular model kit and use it as you study.  A solid understanding of the three-dimensionality of organic molecules is key to doing well in this course.  We will occasionally take time in class for your to to build models of example molecules.  You may also find computer molecular models useful.  A collection of computer molecular models for the textbook is on the CD that accompanies our text.  The CD also includes reaction animations and tutorials.

Organic Study Sheets

In order to help you focus your learning efforts with the text book, I will be preparing Organic Study Sheets for each chapter that we cover. In these Study Sheets are section by section (of the text book) descriptions of what I desire for you to learn from each chapter. The Study Sheets provide goals for your learning and appropriate emphasis on chapter material. You should use the Study Sheets as you read the text. At the bottom on the printed copies of the Study Sheets handed out in class are listed the problem assignment for each chapter.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

Use of Computers

Electronic tools will supplement this class in several ways. a) Personal email will facilitate communication on a one-on-one basis between you, your peers, and myself (fryhle@rainier.chem.plu.edu). b) I have set up an email discussion list that can be used for informal class-wide communication among subscribers. The address is organic@rainier.chem.plu.edu (italics only for emphasis). You must subscribe to the discussion list in order to participate. Please see the instructions below for instructions on how to subscribe to the list. c)  There is a CD ROM that comes with your textbook which has molecular models and Concept Unit tutorials on it, d) Information about the course is available on the World-Wide Web (at http://rainier.chem.plu.edu/chemdept/organic.html). Various free software and study aids are available over the Internet. See the Organic Tool Kit page, as well.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading
Email

A word about my intended use of email in this class. I expect that every one of you will have a PLU email account for use in this class. I will only use your PLU email address for communication with you (not AOL, Hotmail, Yahoo, etc.), and I won'tl  respond to messages from non-PLU email accounts for students in this class.  (This is a University Policy for faculty email communication with students.)  Computers are available for your use in Rieke Science Center and in the computer user rooms on campus. To use Rieke Science Center computers you will need a password that I will give you in class.  My plan is to receive by email your suggested topics for class discussion and problem requests, and also to send you information, assignments, and responses to your questions by email. I usually check my mail several times each work day.  My preferred email address is fryhle@rainier.chem.plu.edu, as noted above. (Please use this address rather than fryhlecb@plu.edu.)

The Organic Journal Club - An Email Discussion List

I expect that with establishment of your email account you will subscribe to the PLU email discussion list called organic. To subscribe, send an email message to majordomo@rainier.chem.plu.edu with nothing but Subscribe organic in the body of the message (italics only for emphasis). You must subscribe from a PLU email address.  I will remove any subscribers from addresses outside PLU.  Once subscribed through this message, all of your future messages to the list should be addressed to organic@rainier.chem.plu.edu. The Organic Chemlist will be used by me to post class-wide announcements, lecture clarifications, and replies to some of your questions. You are also encouraged to use it among yourselves to arrange impromptu study sessions, discuss organic chemistry with each other, and in general communicate about anything germane to Organic at PLU.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

The Organic Journal Club (TOJC)

Archives of TOJC On-Line!

Organic I - Fall 1996

Organic I - Spring 1997

Organic II - Fall 1997

TOJC September 1996 Archive 
TOJC February 1997 Archive 
TOJC September 1997 Archive 
TOJC October 1996 Archive 
TOJC March 1997 Archive 
TOJC October 1997 Archive 
TOJC November 1996 Archive 
TOJC April 1997 Archive 
TOJC November 1997 Archive 
TOJC December 1996 Archive 
TOJC May 1997 Archive 
TOJC December 1997 Archive 
The Organic email discussion list will also serve as the electronic medium for The Organic Journal Club (TOJC). TOJC will be a communal diary of the class's learning of organic chemistry. The goal of TOJC is to stimulate a ferment of class-wide discussion about current topics in organic and provide a living record of our learning process. Participation in The Organic Journal Club is an optional part of the course. No credit will be given for messages.  Archives of participation in The Organic Journal Club by previous classes can be reached by following the links above. Messages are sorted by subject, thread, author, and date.

The following are guidelines for participation in The Organic Journal Club:

World-Wide Web

To increase your access to course information I have provided this course outline and other course information over the World Wide Web at http://rainier.chem.plu.edu/organic.html. You can also access it through links from my home page (http://rainier.chem.plu.edu/fryhle.html). These pages include links to the software and Internet resources mentioned below.

I've put a few worked-out problems on the web called Problem Assist!. These are under development.

Supporting Software and Data

There is a wealth of software and computerized resources available to support courses in organic chemistry. Much of this is available free over the Internet, including software for drawing chemical structures and importing them into formal reports (ISIS /Draw), software for viewing computerized molecular models in three dimensions (Rasmol), archives of organic structures for use with Rasmol, and spectroscopic data and processing programs. Links to this software can be found on my home page (http://rainier.chem.plu.edu/fryhle.html) and the Organic Chemistry Home Page (http://rainier.chem.plu.edu/chemdept/organic.html).

CD Molecular Models and Concept Units

Computer molecular models are available on the CD that accompanies our text. These models are listed in the on-screen index of the CD. (I do not consider these substitutes for hand-held models, howevever. Both types have their specific benefits.) There are also a number of tutorials about topics in the book, called Concept Units as well as some computerized drill problems. The Concept Units were created by Darrell Woodman, University of Washington.

Course Overview (Top) Philosophy Course Calendar Organic Study Sheets Classroom Activities Learning Groups
Homework Use of Computers Email The Organic Journal Club (TOJC) CD Resources and Molecular Models Academic Policies and Grading

Academic Policies

I expect that all of your work for credit will be done strictly in the spirit of academic honesty. I trust that each one of you will conduct your work with the highest level of integrity. Furthermore, I expect that each of you will assist in maintaining an atmosphere of honesty by bringing to my attention any lapse in academic honesty you observe. Any breach of academic honesty will receive a severe penalty. In this case, withdrawal from the course will not be possible. Grading

Exam and graded exercises will follow the point distribution described above and also shown below. In order to encourage cooperative learning among all members of a Learning Group, all members of a Learning Group will receive a 15 point Earned Bonus on a given exam score if every member of that Learning Group scores above 75% on any particular exam.

Point Distribution

Three Exams @ 100 Points Each 300 Points
10 Best In-Class Exercises @ 10 Points Each 100 Points
2 Learning Group Problems @ 35 Points Each 70 Points
Final Exam 150 Points
Possible Learning Group Earned Bonus 15 Points/Exam
Final grades will be based on the sum of all the points earned during the course. In order to reduce competition and encourage cooperative learning final grades will be assigned according to an absolute point scale. (If necessary, however, I may make in dividual or global adjustments to this scale.)

Absolute Scale for Final Grades

Grand Total of Points Percentage of Grand Point Total Final Grade
543-620 88-100 A-, A, A+
443-542 72-87 B-, B, B+
338-442 55-71 C-, C, C+
233-337 38-54 D-, D, D+
0-232 0-37 E

University Policy: If you need course adaptations or accommodations because of a documented disability, if you have emergency medical information to share with me, or if you need special arrangements in case the building must be evacuated, please make an appointment with me as soon as possible (Rieke 240, X8314), and please contact the Coordinator for Students with Disabilities (Alene Klein, Counseling and Testing Office, Ramstad Hall 106, X 7206).  Official notification to the instructor of any disability conditions that may impair a student's academic performance must come from the Coordinator for Students with Disabilities. Without advance warning, such difficulties can not be used later as the basis for requesting make-up course work or reconsideration of grades.

232sy_2000.html

Last Modified 9/8/2000

Copyright, 2000, Craig B. Fryhle