In order to understand life phenomena in atomic and molecular levels, a deep knowledge about organic chemistry is indispensable. On the other hand, some graduate students might have not gotten enough education on organic chemistry and yet may face the necessity for grasping their study subjects in atomic level. This organic chemistry course aims to give the fundamentals for "the ability to see the world in atomic and molecular levels" to all the students from the beginners to intermediate students by covering from a high school chemistry to advanced organic chemistry.
In the first four lectures, students will focus on the selected topics in undergraduate organic chemistry, thereby lay a foundation on organic chemistry. In the middle stage, where the conversions of functional groups are detailed, students will learn the fundamentals required for organic synthesis and ability to consider various reaction mechanisms at molecular and atomic levels. In the end, students will be able to thoroughly understand the synthetic pathways to natural products and pharmaceutical drugs at molecular and atomic levels.
Organic reaction mechanism, Organic electron theory, Molecular orbital theory, Functional group conversion, Retro synthesis, Natural product synthesis, Synthesis of medicinal drugs
|Intercultural skills||Communication skills||Specialist skills||Critical thinking skills||Practical and/or problem-solving skills|
Four professors are responsible for this course. Each lecture will start with about 10 min summary of the previous lecture. At the end of each class, the points will be briefed. Handouts will be given in each class.
|Course schedule||Required learning|
|Class 1||Structure of organic compounds||Introductory organic chemistry taught in high school and university, Octet rule|
|Class 2||Reactivity of organic compounds||Acids, bases, polarizability|
|Class 3||Functional groups and their properties||Electron withdrawing, resonance|
|Class 4||Organic reaction mechanisms||Drawing "arrows" to indicate electron shifts|
|Class 5||Functional group conversion 1: derivatization to leaving groups||Nucleophilic addition-elimination reaction|
|Class 6||Functional group conversion 2: nucleophilic substitution||Nucleophilicity, leaving ability, solvent effect|
|Class 7||Functional group conversion 3: addition reaction, oxidation-reduction||Multiple bonds|
|Class 8||Synthesis of natural products||Retrosynthetic analysis, C-C bond formations|
|Class 9||Synthesis of medical drugs||Costs, Toxicity, Bioactivity|
|Class 10||Chemistry of nucleic acids||Phosphoric acids, hetero cyclic compounds|
|Class 11||Protecting group 1: Protection of alcohols and amines in nucleic acid syntheses||Ethers, esters, amides|
|Class 12||Synthesis of natural and artificial nucleic acids||DNA, RNA, Antisense oligonucleotides, aptamers|
|Class 13||Chemistry of carboxylic acids and related compounds||Dehydration condensation|
|Class 14||Protecting group 2: Protection of amines and carboxylic acid in peptide syntheses||Orthogonality|
|Class 15||Synthesis of bioactive peptides||Hormones, medicinal drugs|
Essential graduate courses for bioscience and bioengineering - organic chemistry, H. Yuasa, ed, TokyoTech Press (2011).
Organic Chemistry: Structure, Mechanism, and Synthesis, R.J. Ouellette and J. D. Rawn, Elsevier (2014)
Advanced Organic Chemistry, Fifth Edision, Part B: Reactions and Synthesis, F.A. Carey and R. J. Sundberg, Springer (2007).
Small tests given in the classes (20%). Achievement is evaluated by a term-end examination (80%).