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Synthesis 2
Introduction to Organic Synthesis
Jon R. Parquette
Chemistry 6430 MWF 3:00-3:55 PM
Fall 2022 McPherson 2017
Zoom Link
https://osu.zoom.us/j/5120258277?pwd=bk4wVXhQVmQ2OXJLbWp5U1JHY3RzQT09
Meeting ID: 512 025 8277
Password: parquette
Instructor: Professor Jon Parquette (Office: 181 CBEC; e-mail [email protected]io-state.edu;
phone 2-5886).
Office hours: By appointment in-pserson or via Zoom (using Zoom link above).
Course Format: Three in-person lectures (55 min. per lecture) per week.
Teaching assistant: Tongyue (Tori) Chen ([email protected]); office hours: by
appointment
Lectures. Lecture content will presented in-person (MWF 3:00-3:55 PM).
Course Description. This course will cover key concepts in organic synthesis and is primarily intended
for graduate students and advanced undergraduates. The goal of this class is to explore different synthetic
strategies for performing highly selective oxidative and reductive transformations, focusing on important
elements of chemo-, regio- and stereoselectivity. In addition, this course will cover fundamental chemical
principles of orbital controlled reactions such as cycloadditions and electrocyclic reactions. Students will
learn how to exploit these transformations in the context of designing synthetic routes to a range of
organic target molecules.
Textbooks: Most of the information provided in this course comes from the primary literature rather than
textbooks. Background reading in Organic Chemistry (Part B) by Carey and Sundberg and in Modern
Methods of Organic Synthesis by Carruthers will be assigned to supplement the primary literature.
Additional references from literature will be added to supplement and update the relevant sections of
these books. You should purchase the these two books, Carruthers and Carey/Sundberg, as we will
be covering many topics in them. I encourage you to look up many of these papers on-line.
Texts and study aids:
Modern Methods of Organic Synthesis (4
th
Edition) by William Carruthers and Iain Coldham
!
Advanced Organic Chemistry (Part B, 5
th
Edition) by Francis Carey and Richard Sundberg!
Strategic Applications of Named Reactions in Organic Synthesis by Laszlo Kurti and Barbara
Czako
Modern Physical Organic Chemistry by Eric Anslyn and Dennis Dougherty
To fully understand the chemistry that we will be discussing in lecture, you should look up most of the
references cited in the lecture notes. You can access most of the libraries journals electronically back to
1995-1996 via Ohiolink and any American Chemical Society Journal back to the 1800's via the internet:
Ohiolink: http://journals.ohiolink.edu/ejc/alpha.cgi
ACS Journals: http://pubs.acs.org/about.html (on campus).
From Home: you need to enter the site via proxy:
(http://pubs.acs.org.proxy.lib.ohio-state.edu) and then enter your university login and
password.
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Problem sets: Problem sets and the solutions are provided online on CarmenCanvas and in hard copy
format in two spiral books. I recommend that you work as many of the problems that are given in Carey
and Sundberg as possible. Several problem sets with associated answer keys will be distributed in class.
These problem sets are provided for your benefit-they will not be graded.
Technology Requirements:
CarmenZoom: CarmenZoom is a service provided by OSU at osu.zoom.us. System Requirements: an
internet connection (broadband wired or wireless 3G or 4G/LTE); speakers and a microphone; a webcam
or HD webcam. For more information on supported browsers and operating systems see
support.zoom.us/hc/en-us.
CarmenCanvas CarmenCanvas is a service provided by OSU at carmen.osu.edu.
Health and safety requirements: All students, faculty and staff are required to comply with and stay up to
date on all university safety and health guidance (https://safeandhealthy.osu.edu), which includes
wearing a face mask in any indoor space and maintaining a safe physical distance at all times. Non-
compliance will result in a warning first, and disciplinary actions will be taken for repeated offenses.
Grading System: The final grade will be determined by performances on one, in-class midterm, and one
comprehensive final exam. The midterm exam will account for about 43% and the final exam 57% of
your final grade. You will need to contact me in advance of missing the exam and provide a validated
reason for missing the exam
To encourage all of you to work together, this course will not be graded on a strictly competitive curve
system. The grading scale will be adjusted based on the examination statistics similar to a curve system.
However, you will be guaranteed a grade based on the grade scale shown below, irrespective of the exam
averages. For example, even if the average score on the exams was 85%, you would still be guaranteed
some form of an “A”, not a “C” as required by the curve system. So, you are never penalized by higher
class performance. I will never increase the percentage required for a given grade.
Grade Scale
A 85-100%
B 75-85 %
C 60-75%
D 50-60%
E below 50 %
Grades at either end of the ranges in the grading scheme will be assigned + or - as appropriate.
Midterm I Nov. 18 Friday 150 pts.
Final examination Dec. 9 Friday 12:00- 1:45 PM 200 pts.
Class Attendance Policy. Students are expected to attend every lecture. Although we will not specifically
take attendance, students are responsible for everything covered or discussed in each lecture.
Occasionally, there will be extra credit quizzes offered in lecture and you must be present in lecture to
participate in them.
Other Important Dates.
Nov. 11 Veterans Day-No Class (falls on a Friday)
Wed-Fri, Nov. 23-25: Thanksgiving Day and Columbus Day observed --no classes, offices closed.
Wed., Dec. 7: Last day of classes
Approximate Weekly Topical Coverage
3
General Topics Covered
Topics Reading
1. Reduction Chemistry (2 wks) C/S Chp. 5; Carr. Chp. 7
A. Reduction of Carbon-Carbon p-Bonds
B. Reduction of Carbon-Heteroatom Bonds
C. Stereoselectivity
D. Reduction of a Functional Group to an Alkane
2. Oxidation Chemistry (2 wks) C/S Chp. 12; Carr. Chps. 4/6
A. Oxidation of Alcohols
B. Oxidation of Carbon-Carbon Bonds
C. Oxidation of Carbon-Hydrogen Bonds
3. Sigmatropic Reactions (1.5 wks) C/S Chp. 6.4-6.6
A. General Characteristics. [i,j] Sigmatropic Shift
B. [3,3] Sigmatropic Rearrangments
C. [2,3] Sigmatropic Rearrangements
D. Vinylcyclopropane-Cyclopentene Rearrangements
4. Cycloaddition Reactions (1.5 wks) C/S Chp. 6.1-6.3.; Carr. Chp. 3
A. General Characteristic of Pericyclic Reactions
B. Woodward-Hoffman Rules
C. Diene/Dieneophile Reactivity
D. Regio- and Stereoselectivity of Cycloaddition Reactions
E. Catalytic Rate Enhancement
F. [2+2] Cycloaddition
G. Ene Reactions
H. 1,3 Dipolar Cycloadditions
Students with Disabilities: The university strives to make all learning experiences as accessible
as possible. In light of the current pandemic, students seeking to request COVID-related
accommodations may do so through the university’s request process, managed by Student Life
Disability Services. If you anticipate or experience academic barriers based on your disability
(including mental health, chronic, or temporary medical conditions), please let me know
immediately so that we can privately discuss options. To establish reasonable accommodations,
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arrangements with me as soon as possible to discuss your accommodations so that they may be
slds.osu.edu; 098 Baker Hall, 113 W. 12
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The Department of Chemistry and Biochemistry promotes a welcoming and inclusive
environment for all students and staff, regardless of race, gender, ethnicity, national origin,
disability or sexual orientation. There is no tolerance for hateful speech or actions. All
violations of this policy should be reported to the OSU Bias Assessment and Response Team
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Homework Problems: Problem solving is essential to learning organic chemistry. You should work all
the homework problems that appear in the assigned reading. Specific problems will be assigned for each;
however, you should try to work as many of the problems at the end of each chapter as you can. The
Study Guide provides detailed answers to the problems. These problem sets will neither be collected nor
graded, they are for your benefit.
Academic Misconduct. It is the responsibility of the Committee on Academic Misconduct to investigate
or establish procedures for the investigation of all reported cases of student academic misconduct. The
term “academic misconduct” includes all forms of student academic misconduct wherever committed;
illustrated by, but not limited to, cases of plagiarism and dishonest practices in connection with
examinations. Instructors shall report all instances of alleged academic misconduct to the committee
(Faculty Rule 3335-5-487). For additional information, see the Code of Student
Conduct http://studentlife.osu.edu/csc/.
Cheating: I will not tolerate any form of academic misconduct. All suspected cases will be dealt with
according to OSU procedures via the Committee on Academic Misconduct. It is the responsibility of the
Committee on Academic Misconduct to investigate or establish procedures for the investigation of all
reported cases of student academic misconduct. The term "academic misconduct" includes all forms of
student academic misconduct wherever committed; illustrated by, but not limited to, cases of plagiarism
and dishonest practices in connection with examinations. Examples of misconduct include, but are not
limited to: (1) violation of course rules; (2) providing or receiving information during quizzes and
examinations; (3) submitting plagiarized or falsified work for credit; (4) falsification, fabrication, or
dishonesty in assignments, quizzes, experiments, or exams; (5) serving as a substitute for another student
on an examination or falsely claiming to have taken an examination; (6) alteration of grades, marks, or
examination answers in an effort to change the earned credit or grade; (7) alteration of University forms
used to drop or add courses, or unauthorized use of those forms. (8) Posting quiz and exam content online
or receiving information regarding its content from the internet at any point during the semes
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on sex and gender are Civil Rights offenses subject to the same kinds of accountability and the same
kinds of support applied to offenses against other protected categories (e.g., race). If you or someone you
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at titleix@osu.edu
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