Chemistry 128 Spring 2006, Organic Synthesis
Instructor: Dr. Cynthia Kellen-Yuen Office: SQU 418C phone: 278-3528
E-mail: ckyuen@csus.edu office hours: M, W, F:
Text: Advanced
Organic Chemistry Part B: Reactions
and Synthesis, fourth edition, by Carey and Sundberg
Web site: Listed under chemistry department web pages: www.chem.csus.edu/ckyuen
and on
WebCT at online.csus.edu.
Course Description: Application of functional
group reactions to multi-step syntheses.
Recently developed synthetic methods and literature searching will be
emphasized.
Course
prerequisites:
Successful completion of Chemistry
124 (with a grade of C).
Learning Objectives:
Students will be able to
recognize various types of synthetic transformation reactions and utilize these
reactions to perform multi-step syntheses of organic molecules. Students will become familiar with protecting
groups and their use in these multi-step syntheses. Understanding and drawing of reaction
mechanisms will be emphasized.
Grading:
Quizzes (20 pts each) 100
Problem sets 150
Exams (100 pts each) 300
Final 200 .
Total 750 pts
Letter grades are assigned based on a range of: A to A- = 88% and above, B+ to B- = 87-78%,
C+ to C- = 77-66%, D = 65-55%, F = Below 55%
Quizzes:
Quizzes will be short 10-15 minute problems at the end of class. Keep the best 5 of 7 scores. No Make-ups. These quizzes will cover the current topic under discussion.
Problems:
Problem sets will be
assigned throughout the semester and will be handed in for grading. In addition, please remember that there are
problems at the end of each chapter in your book. Even if these are not assigned, TEXTBOOK problems make for good test
questions! The material covered this
semester cannot be understood well enough to get a passing grade by simply
attending lecture. You must read the
chapters in advance of the lectures and do practice problems outside of class
or you will fall behind. It is HIGHLY recommended that you attempt all
of the problems within the chapter in order to gauge your comprehension of the
material.
Exams:
Three 100 point exams will
be given through the course of the semester.
The exams will mainly consist of three kinds of questions: 1) What are the
organic products of a given reaction?; 2) Write out a reasonable mechanism for
a given transformation; and 3) What reagents / conditions could be used to
perform a given transformation? You may
have ONE 3 x 5 inch note card for the exam on which you may write whatever you
deem helpful on one side of the card.
The only stipulation is that the notes must be hand written, not
printed or photocopied. No magnifying
glasses are allowed. Since each exam builds on
old material, each exam should be considered cumulative.
There are no make-up
exams; one missed exam may be made up with the score from the final exam.
Final:
The final for this class
is scheduled for Friday, May 19th from
Lectures:
We will begin the year
with a review of concepts from Chem 24 and 124.
We will cover Chapters 1, 2, 3, 4, 5, 7,
and 12 in the textbook.
Please use the schedule below to keep track of where we are in the
lecture. General dates for tests are
indicated, but rely on class announcements for the exact timing.
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Week of: of: |
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Monday
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Wednesday
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Friday
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1/23 |
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Review |
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Review |
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1/30 |
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Quiz 1 |
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2/6 |
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Quiz 2 |
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2/13 |
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Exam 1 |
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2/20 |
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2/27 |
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Quiz 3 |
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3/6 |
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Quiz 4 |
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3/13 |
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NO CLASS |
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NO CLASS |
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NO CLASS |
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3/20 |
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3/27 |
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Exam 2 |
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4/3 |
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Quiz 5 |
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4/10 |
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Quiz 6 |
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4/17 |
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4/24 |
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Quiz 7 |
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5/1 |
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Exam 3 |
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5/8 |
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5/15 |
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Cumulative Final |
Suggestions
for Study:
There are as many different methods to study as
there are people who study. No one
method works for everyone. Only one
principle is unalterable: you MUST
study. Devote some time to study each
day and you will not be overwhelmed at test time. Since everything in organic chemistry builds
up from the same foundation, not understanding the basics will mean not
understanding anything based upon it.
GET YOUR QUESTIONS ANSWERED IMMEDIATELY or you will very quickly get
lost.
One method of study that is highly recommended by
previous 128 instructors is the 3 x 5 flashcard method. Place a reaction on one side with all the
pertinent notes about conditions but no clues as to products. On the reverse side write the product and any
notes about the reaction (exceptions, necessary protecting groups, etc.) Make cards for reactions from the lecture,
from the text, and from old Chem 24 and 124 exams (particularly those which
have caused you problems on old exams).
Since each exam builds on old material, each exam is cumulative.
Practice drawing mechanisms with curved arrows for these
reactions, as this will provide the logic behind each transformation which will
give you the power to predict the products of unknown reactions.
Mechanism Tips: When writing a mechanism
remember the basic rule—whatever is most reactive dominates the process. Show all arrows for each step of the reaction
path, and show all intermediates.
Resonance structures are important because the can emphasize the fact
that many compounds can react at more than one site. Finally, do not take shortcuts—Do not write
“PT” in place of showing arrows for proton movement, and DO NOT indicate any
“naked protons” (H+) in any mechanisms! Mechanistic understanding is at the heart of
all complex, multi-step reactions and will be fundamental for any future work
in graduate school.
Cheating:
Cheating in any way, shape, or form is not tolerated
in this class. A student caught cheating
will receive a zero on that quiz/exam and it will count towards the student's
final grade. If a student is caught a
second time, the student will fail this course.
Cheating includes copying from another student's paper, using extra
materials during testing, programming data into a calculator, having other
people take tests for you, altering exams after they have been graded,
etc.
Special Needs:
Any student needing special accommodations should
see the instructor immediately.