The objects of bioscience and biotechnology are apparently organic compounds. Thus, this lecture systematically and comprehensively describes fundamental topics necessary for the use of or the research on organic compounds, including the knowledge and theory on their nomenclature, nature, analysis, reactions, synthesis, and utility. The contents consist of the IUPAC nomenclature, the electronic states and bonding of molecules, three-dimensional structures of molecules, the instrumental analysis of molecular structures (NMR, IR, Ms), reactions of each functional group, the carbon-carbon bond formation and organic synthesis, and utility of natural and artificial organic compounds, which will be lectured according to the textbook, with the theoretical background and relationship between the topics being mentioned.
At the outset, this course allows the student to firmly learn the general knowledge and theory common to individual topics, such as the nomenclature of compounds, electronic states and bonding of molecules and their nature and structures owing to the former, and the electronic theory of organic chemistry essential to the description of reaction mechanisms. At the next stage, the students will proceed to study reactions unique to each functional group and the instrumental analysis of molecular structures, which are not only memorized but also well interpreted by them on the basis of the above general notion. While reviewing the previous two steps, the students are requested to increase their ability to understand the application of the fundamental topics, for example, the synthesis of organic compounds and utility of natural and artificial compounds. As a whole, this lecture will provide students basic knowledge and theory of organic chemistry and, at the same time, its covering area of utility of organic compounds.
By the end of this course, students will be able to:
1. Give names to organic compounds, with seeing their structures, and vice versa.
2. Understand the electronic states and bonding of organic molecules and explain their nature and structures based on the former.
3. Discuss reaction mechanisms with appropriate flow of electrons based on the electronic theory of organic chemistry.
4. Show characteristic reactions of individual functional groups.
5. Make synthetic plans of organic compounds by the functional-group manipulation and carbon-carbon bond formation.
6. Imagine synthetic utility of natural and artificial organic compounds.
Structure and Bonding in Organic Molecules, Structure and Reactivity (Acids and Bases, Polar and Nonpolar Molecules), Reactions of Alkane, Cycloalkanes, Stereoisomers, Properties and Reactions of Haloalkanes (Bimolecular Nucleophilic Substitution), Further Reactions of Haloalkanes (Unimolecular Substitution and Pathways of Elimination)
|Intercultural skills||Communication skills||Specialist skills||Critical thinking skills||Practical and/or problem-solving skills|
The lecture is to be done in order according to the textbook. (Thus, students are encouraged to familiarize the expected pages of the textbook in advance to the class and to review them after the class.) Students are given concise exercise problems for the last 10 minutes of each class, and their solutions and remarks will be explained at the beginning of the next class.
|Course schedule||Required learning|
|Class 1||Ionic and Covalent Bonds||The Octet Rule, Lewis Structures, Resonance Forms|
|Class 2||Hybrid Orbitals||Atomic Orbitals, Molecular Orbitals, Hybrid Orbitals|
|Class 3||Acids and Bases||Acids and Bases, Kinetics and Thermodynamics of Chemical Reactions, Electrophiles and Nucleophiles, Functional Groups|
|Class 4||Structural and Physical Properties of Alkanes||Straight-Chain and Branched Alkanes, Naming the Alkanes, Rotation about Single Bonds|
|Class 5||Structure of Alkyl Radicals||Strength of Alkane Bonds, Hyperconjugation, The Radical Chain Mechanism|
|Class 6||Radical Halogenations, Comprehension Test (1)||Radical Halogenations of Methane, Chlorination of Higher Alkanes (Relative Reactivity and Selectivity)|
|Class 7||Names and Physical Properties of Cycloalkanes||Ring Strain and the Structure of Cycloalkanes, A Strain-Free Cycloalkane|
|Class 8||Substituted Cyclohexanes||Larger Cycloalkanes, Polycyclic Alkanes|
|Class 9||Chiral Molecules||Optical Activity, Absolute Configuration (R-S Sequence Rules），Fischer Projections|
|Class 10||Stereochemistry in Chemical Reactions, Comprehension Test (2)||Racemic Mixtures, Enantiomers, Separation of Enantiomers|
|Class 11||Nucleophilic Substitution||Physical Properties of Haloalkanes, Reaction Mechanisms and Kinetics of the Nucleophilic Substitution|
|Class 12||Stereochemistry of the SN2 Reaction||Frontside or Backside Attack, Structure and SN2 Reactivity (The Leaving Group and the Nucleophile)|
|Class 13||Unimolecular Nucleophilic Substitution||Stereochemical Consequences of SN1 Reactions, Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular SN1 Nucleophilic Substitution|
|Class 14||Unimolecular Elimination||E1, Competition Between Substitution and Elimination|
|Class 15||Bimolecular Elimination, Comprehension Test (3)||E2, Competition Between Substitution and Elimination|
Organic Chemistry - Structure and Function, 6th ed., K. P. C. Vollhardt and N, E. Schore, W. H. Freeman and Co., New York, 2011; The Japanese translation, 6th ed., Kagakudojin, Kyoto, 2011. (Japanese)
Study Guide and Solutions - Manual for Organic Chemistry, 6th ed., N, E. Schore, W. H. Freeman and Co., New York, 2011; The Japanese translation, 6th ed., Kagakudojin, Kyoto, 2011. (Japanese)
Students will be assessed on the concise exercise problems in each class (30%) and Comprehension Tests 1-3 (70%).
Akihiro Ohkubo (aohkubo[at]bio.titech.ac.jp) Hiroyuki Nakamura (hiro[at]res.titech.ac.jp)
Wednesday (10:00-12:00), A prior contact by e-mail is needed.
As there is no duplication of the contents from Organic Chemistry I (alkanes and haloalkanes) to IV (carbonyl compounds and amines), the systematic study in this order will maximize its efficiency. Therefore, students are advised to enroll all of them in serial order. After completion of these courses, more advanced lectures, Bioorganic Chemistry and Pharmaceutical Chemistry, are available. Thus, students can proceed to the higher level of organic chemistry by taking one or both of them, dependent on their interest.