CHEM 534, Advanced Organic Chemistry
Western Illinois University, Spring 2016
Instructor: Dr. Jin Jin, Currens Hall 430-A (email: j-jin@wiu.edu) (phone 298-2261)
Lecture: 5:00-6:15 am; Tue, Thur in Currens 202
Office Hours: Monday, Wednesday, Friday 10:00-11:30 am, or by appointment.
Textbook and materials:
A. Organic Chemistry, Clayden, Greeves, Warren and Wothers; Oxford University Press,
2001 (ISBN: 978-0-19-850346-0)
B. Advanced Organic Chemistry 4th edition Part B, Carey and Sundberg, Kluwer
Academic/Plenum Publishers, (ISBN: 0-306-46245-1)
C. Name Reactions: A collection of detailed reaction mechanisms 2nd edition, Jie Jack Li,
Springer, (ISBN: 81-8128-022-9)
Course Description: A comprehensive survey of the chemistry of carbon compounds: their
structure, properties, bonding, stereochemistry, reactions, and reaction mechanisms. Standard
synthetic transformations will be discussed from a structural, stereochemical and mechanistic
point of view. Common functional group transformations in multi-step synthesis including
retrosynthetic analysis will also be discussed.
Grading:
Lecture Examinations (100 pts x 3)
Final Examination
Assignments (20 pts x 10)
Research Term Paper
Presentation
TOTAL
300 pts
150 pts
200 pts
100 pts
50 pts
800 pts
Grading Scheme
Total Pts
720-800
640-719
560-639
Grade
A
B
C
Total Pts
480-559
0 - 479
Grade
DF
Exams: There will be three 100-point lecture exams and a 150-point comprehensive final exam
this semester. Each exam will cover material from lectures, any handouts, and the textbook. You
will be responsible for all material up to each test. Do not be late (you have limited time) or miss
exams. You will not be able to make them up unless you have a written medical excuse or
documentation otherwise justifying your absence.
Assignments: There will be ten assignments this semester and each one takes 20 pts. Please
remember that you are expected to do your own work at all times. You can’t copy from your
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classmates. If plagiarism is found, everyone involved will be given zero point and will fail the
course if found more than once. Assignments turned in late (for any reason) will have two
points deducted per day; if turned in two weeks after the due date it will not be graded.
Research Term Paper: The term paper must be based on a topic of organic chemistry relevance
and must be chosen in consultation with the instructor. It is strongly encouraged that you start
working on your term paper early in the semester. The topic along with the major articles
should be approved by the instructor by March 10, 2016. The paper is to be approximately 1015 pages (typed and double-spaced) and must include no less than ten research journal
references with publication dates 2000 or later. The term paper must be your own work and
in your own words. Sources of ideas or information must be referenced. The term paper will be
graded based on content, construction and conciseness. The paper is due on or before May 5th.
Incidents of plagiarism will result in a grade of zero for the assignment and may result in a
failing grade for the whole course.
Presentation: Research term paper presentation by students will be scheduled during the weeks
of May 3rd. The presentation should be based on ten papers, which are involved in your term
paper. The presentation should be about 15 min long.
Attendance: Attendance will be taken for each class. Each absence will lower your total grade
by 5 points. You are expected to attend class regularly and punctually. Excessive absences will
be reported to the financial aid office. If you anticipate or suffer an absence by emergency or
tragedy, it may be possible to make up missed work. Notify the course instructor at the earliest
opportunity. Students who are called away from the campus to participate in University
sponsored trips such as athletics or professional meeting may be allowed to make up missed
work if the student provides a signed memo from the faculty sponsor.
Web Resources: The course homepage is on the Western Online. Information for this class will
be posted there, including the course syllabus, homework problem sets, quizzes, exams, their
answers and your grades. Any class announcements will also be posted here.
Emergency evacuation: If a fire alarm should happen to ring, or if students are ordered to
evacuate a lab or classroom by the instructor, the students should walk to the nearest stairwell
(Do not use the elevators) and proceed to the ground floor and out the building. Any student on
an upper floor who cannot physically proceed down the stairs should go to the southernmost
stairwell and await assistance. If the building should be evacuated all students and personnel
should gather at the southwest corner of the Higgins Parking lot near the fence (parking lot just
outside the building) to wait further instructions. Also, the campus emergency management
office has two videos at the beginning of the semester. These videos are titled "Shots fired and
College Fire Survival" and can be found at the following web
site: http://www.wiu.edu/rmep/resources.php.
WIU Policies: It is the policy of Western Illinois University to accommodate individuals with
disabilities pursuant to federal law and the University's commitment to equal educational
opportunities. It is the responsibility of the student to inform the instructor of any necessary
accommodations at the beginning of the course. Any student with a disability requiring
accommodations should contact the Office of Disability Support Services.
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Statement on Ethics. Western Illinois University, like all communities, functions best when its
members treat one another with honesty, fairness, respect, and trust. Students have rights and
responsibilities. The following action is prohibited under the Student Conduct Code: Disorderly
Conduct: Any behavior which disrupts the regular or normal functions of the University
community, including behavior which breaches the peace or violates the rights of others.
Plagiarism, cheating, and other forms of academic dishonesty constitute a serious violation of
University conduct regulations. Any student convicted of academic dishonesty, can receive a
failing grade and may be subject to further academic penalties. Web address for Academic
Integrity Policy (http://www.wiu.edu/policies/acintegrity.php). Please remember that you are
expected to do your own work at all times. You can’t directly copy the homework or quizzes
from your classmates. However, discussing homework questions or quizzes with your
classmates is fine.
Tentative Lecture Schedule
Date
Topic
Chapters in the
text
Jan 19/21
Chapter 26 Clayden
Chapter 27 Clayden
Feb 2/4
1. Alkylation of enolates
2. Aldol condensation
3.Claisen reaction
4. Michael addition
5. Retrosynthesis
Feb 9/11
6. Pericyclic reaction
Chapter 35 Clayden
Feb 16/18
7. Rearrangement
Chapter 37 Clayden
Feb 23/ 25
8. Free Radical reaction
Chapter 39 Clayden
Mar 1/3
9. Organometallic reaction
Chapter 48 Clayden
Mar 8/10
10. Aromatic substitution
Chapter 11 Carey
Mar 15/ 17
Spring Break
Mar 22/ 24
11. Oxidation and Reduction
Chapter 5/12 Carey
Mar 29/ 31
12.Protection and Deprotection
Chapter 13 Carey
Apr 5/7
Special topic I
Total synthesis
Apr 12/14
Special topic II
Apr 19/21
Special topic III
Organic reaction
mechanism
worksheet
Name reactions
Apr 26/28
Student presentation
May 3
Student presentation
May 5
Final Exam 5:00 pm
Jan 26/28
Exam date
Chapter 28 Clayden
Chapter 29 Clayden
Chapter 30 Clayden
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Exam #1
Exam #2
Exam #3