Nagoya University, School of Engineering Lecture information system (SYLLABUS)

Organic Chemistry IV(2.0 credits)

Code:10186
Course Type:Specialized Courses
Class Format:Lecture
Course Name : Chemistry
Starts 1 : 3 Spring Semester
Elective/Compulsory : Elective
Lecturer : Jiyoung SHIN Designated Professor 

•Course Purpose
The primary purpose of this course is to acquire a logical framework for understanding advanced organic chemistry. The course begins with condensation reactions of carbonyl and amine compounds and moves on to various reactions comprising migration steps. It also continues heterocyclic chemistry and organometallic chemistry, which are rapidly-expanding fields. Organometallic compounds that incorporate the carbon-metal bonds as powerful nucleophiles have been widely used for effective synthetic transformation. Replacement of the first metal by a new one can activate or control the chemical reactions' outcomes. Based on the knowledge, the participants are expected to conduct how to perceive appropriate answers to challenging problems in organic chemistry.

•Prerequisite Subjects
Fundamental Chemistry I and II, Organic Chemistry I, II, and III

•Course Topics
Class 1. The reaction of Carbonyl Compounds --- Formations, Condensations, Reaction of Conjugated Carbonyl Compounds; Protection of Acyl Group; Decarboxylation of beta-Carbonyl Carboxylic Acid.
Class 2. Amines --- Preparations of Amines (by Subsequent Alkylation, Reduction of Nitrile, Reduction of Imine, Reduction of Azide, Hydrogenation of Amide, Hofmann Rearrangement, Mannich Reaction, Gabriel Phthalimide Synthesis).
Class 3. Amines --- Reactions of Amines (Alkylation, Acylation, Hoffmann Elimination).
Class 4. Six-Membered Aromatic Heterocycles (Pyridine, Pyridazine, Pyrimidine, Pyrazine, Pyridine Derivatives, and PCC) --- Electron Configuration and Reactivity of Pyridine; Preparation of Pyridine; Pyrillium ion & Pyrones; Tautomerization of Hydroxypyridine into pyridone; Preparation of Pyridone.
Class 5. Preparation and Nucleophilic/Electrophilic Substitutions of Pyridine N-oxides; Reactivity of Pyridine N-Oxide and Pyridine with Electron Donating Groups in Electrophilic Substitutions.
Class 6. Five membered Aromatic Heterocycles (Pyrrole, Pyrazole, Imidazole, and Triazole) --- Electron Configuration of Pyrrole and Reactivity for Electrophilic Substitution; Electrophilic Substitutions of pyrrole (Bromination, Acylation, Mannich Reaction, Nitration, Polymerization); Preparation of Pyrrole.
Class 7. Five membered Aromatic Heterocycles --- Reaction of Pyrrole (Decarboxylation, Acid-Catalyzed Intermolecular Condensation, Porphyrin Synthesis); Reaction of Thiophene (Friedel Crafts Acylation of 2-Methyl Thiophene); Reaction of Furane (Bromination, Acetal Formation, Ring Opening).
Class 8. Fused Heterocycles (Quinoline, Isoquinoline, and Indol) --- Substitution Trends of Quinoline and Isoquinoline (Electrophilic and Nucleophilic Reactions); Preparation of Quinoline; Substitution Trends of Indol; Preparation of Indol.
Class 9. Assessment of Classes 1-8 (Problems and Solutions).
Class 10. Ring Formation from pai-Conjugation – Electrocyclizations (Thermal & Photochemical Reactions); Cycloadditions (Diels-Alder Reactions); Sigmatropic Rearrangements (Cope Rearrangement, Claisen (General, Johson-Claisen, Eschenmoser-Claisen, Ireland-Claisen) Rearrangements, Sulfoxide Formation Through [2,3] Sigmatropic Rearrangement).
Class 11. Ring Expansion or Ring Shrinking Reactions --- Baeyer Villiger Oxidation; Beckmann Rearrangement; Tiffeneau-Demjanov Rearrangement; Favoskii Rearrangement; Wagner Meerwein Rearrangement.
Class 12-13. Organotransition Metal Chemistry: Electronegativity Differences and Organometal Reactions; Pd-catalyzed Cross Couplings (Negishi, Kumada, Stille, Suzuki-Miyaura, Sonogashira, Hiyama, Mizoroki-Heck Cross Couplings).
Class 14. Organotransition Metal Chemistry: Oranometal Catalyzed Metathesis (Grubbs & Schrocks Catalysts and the Cyclic Metathesis); Zigler-Natta Catalysis; Wilkinson Reduction.
Class 15. Assessment of Overall Classes (Final Test and Solution Process).

•Textbook
Organic Chemistry: Structure and Function (Seventh Edition), Peter C. Vollhardt and Neil E. Schore, (W. H. Freeman and Company), New York, 2014, Chapters 21, 23-26.

•Additional Reading
1. Organic Chemistry (Second edition), Jonathan Clayden, Nick Greeves, and Stuart Warren, Oxford, 2012, Chapters 29-30, and 40.
2. Advanced Organic Chemistry (Part B: Reaction and Synthesis, Fifth Edition), Francis A. Carey, Richard J. Sundberg, Springer, 2007, Chapters 7-8.
3. Organometallic Chemistry (Second Edition), Gary O. Spessard, Gary L. Miessler, Oxford, 2010.

•Grade Assessment
Examination (total 70%: midterm (30%) and final (40%)), Assessment of Homework (30%): Credits will be awarded to those students who score 60 or more. Grades are as follows: S(x≧90), A(90>x≧80), B(80>x≧70), C(70>x≧60), and F(60>x). The assessment methods will be reconsidered following a pandemic condition.

•Notes
Submission of "Course Withdrawal Request Form is necessary to withdraw the course. The student needs to contact the course instructor when the student wants to withdraw from the course.
In the cases of any unavoidable reasons such as sickness, accident, or no attendance school, the student may get a grade of 'Absent' through the judgment of the course instructor and the student when the student submits a 'Course Withdrawal Request Form' to receive the 'Absent' grade. No submission of sickness/absence reports and lack of attendance score will result in an 'F' grade: It is for the protection of other attendances in the corresponding course from the frequent absences of the specific/uncertain student(s).
This assessment can be reconsidered within pandemic conditions where the attendance can be replaced with the submission of assignments.

•Contacting Faculty
Students can communicate with the course instructor face-to-face either in the class or through the appointment. Communication through emails (instructor's e-mail: jyshin@chembio.nagoya-u.ac.jp and jyshin321@gamil.com) is also available.
Students are recommended to review the lectures by solving the related homework questions. Each assignment is due by the start of the next class if it is not specially announced.

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