CHEM 221-03 Organic Chemistry I Syllabus Fall 2007

CHEM 534, Advanced Organic Chemistry Western Illinois University, Spring 2018

Instructor: Dr. Jin Jin, Currens Hall 430-A (email: [email protected]) (phone 298-2261)

Lecture: M, W, F 1:00-1:50 pm; in Currens 202

Office Hours: Monday, Wednesday, Friday 9:00-10:20 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)

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) 300 pts Final Examination 150 pts Assignments (20 pts x 10) 200 pts Research Term Paper 100 pts Presentation 50 pts TOTAL 800 pts

Grading Scheme

Total Pts Grade Total Pts Grade 720-800 A 480-559 D 640-719 B 0 - 479 F 560-639 C

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.

1 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 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 9, 2018. The paper is to be approximately 10-15 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 May 4th. 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 April 23 and April 30. 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 3 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

2 accommodations at the beginning of the course. Any student with a disability requiring accommodations should contact the Office of Disability Support Services.

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.p hp). 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.

3 Tentative Lecture Schedule

Week Topic Chapters in the Exam date text 1 1. Alkylation of enolates Chapter 26 Clayden Jan 15-19 2. Aldol condensation Chapter 27 Clayden 2 3.Claisen reaction Chapter 28 Clayden Jan 22-26 4. Michael addition Chapter 29 Clayden 3 5. Retrosynthesis Chapter 30 Clayden Jan 29-Feb 2 4 6. Pericyclic reaction Chapter 35 Clayden Exam #1 Feb 5-9 5 7. Rearrangement Chapter 37 Clayden Feb 12-16 6 8. Free Radical reaction Chapter 39 Clayden Feb 19-23 7 9. Organometallic reaction Chapter 48 Clayden Feb 26-Mar 2 8 10. Aromatic substitution Chapter 11 Carey Exam #2 Mar 5- 9 Mar 12-16 Spring Break 9 11. Oxidation and Reduction Chapter 5/12 Carey Mar 19-23 11 12.Protection and Deprotection Chapter 13 Carey Mar 26-30 12 Special topic I Organic reaction April 2-6 mechanism worksheet 13 Special topic II Exam #3 April 9-13 14 Special topic III April 16-20 15 Student presentation April 23-27 16 Student presentation April 30-May 4 May 9 Final Exam 1:00-2:50 pm