2019 Organic Chemistry III (benzene and ketones)

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Academic unit or major
Undergraduate major in Life Science and Technology
Instructor(s)
Ohkubo Akihiro  Kinbara Kazushi  Fuse Shinichiro 
Course component(s)
Lecture
Day/Period(Room No.)
Tue5-6(H121)  Fri5-6(H121)  
Group
-
Course number
LST.A212
Credits
2
Academic year
2019
Offered quarter
3Q
Syllabus updated
2019/9/4
Lecture notes updated
-
Language used
Japanese
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Course description and aims

The subjects of bioscience and biotechnology are of course organic compounds. Thus, this course systematically and comprehensively describes fundamental topics necessary for the use of or research on organic compounds, including the knowledge of 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, carbon-carbon bond formation and organic synthesis, and the utility of natural and artificial organic compounds, which the instructor will lecture on, following the textbook, mentioning the theoretical background and relationship between topics.
At the outset, this course allows students to get a solid grasp of 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, 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 interpreted by them in detail on the basis of the above general idea. While reviewing the previous two steps, students are requested to improve their ability to understand the application of the fundamental topics, for example, the synthesis of organic compounds and use of natural and artificial compounds. As a whole, this course will provide students with the basic knowledge and theory of organic chemistry and, at the same time, cover area dealing with the use of organic compounds.
Organic Chemistry III will provide a comprehensive overview of alkynes (acetylenes), conjugated olefins, benzene, derivatives of benzene, aldehydes and ketones, their chemical properties, preparation, and reactions. The instructor will also explain how to use the reactions studied here.

Student learning outcomes

By the end of this course, students will be able to:
1. Understand the chemical properties of alkynes, conjugated olefins, benzenes, and substituted benzenes.
2. Learn several syntheses of compounds covered in this course.
3. Learn reactions that are typical of the compounds covered in this course.
4. Design a synthetic method of given compounds possessing alkyne, conjugated olefins, and/or aromatic moiety.

Keywords

Alkyne, Acetylene, Benzene, Aromatic, Electrophilic substitution, Diels-Alder cycloaddition, Friedel-Crafts reaction, Wittig olefination, Aldehydes, Ketones, Addition to carbonyl compounds

Competencies that will be developed

Intercultural skills Communication skills Specialist skills Critical thinking skills Practical and/or problem-solving skills
- - - -

Class flow

The lectures follow the textbook. (Thus, students are encouraged to familiarize themselves with the relevant pages of the textbook before class and to review them after class.) Students are given brief exercise problems for the last 10 minutes of each class, and their solutions and remarks will be given at the beginning of the next class.

Course schedule/Required learning

  Course schedule Required learning
Class 1 Synthesis and biologically active alkynes Synthesis of alkynes and bioactive alkynes
Class 2 Reactions and properties of acetylenes Two pi bonds on alkynes, electrophilic substitution of alkynes
Class 3 Reactions of acetylenes Hydroboration of alkynes, haloalkenes, coupling reaction
Class 4 Allylic and conjugated diene systems Stability, properties, and reactions of allylic compounds and conjugated dienes
Class 5 Delocalized pi systems, Comprehension Test (1) Properties and reactions of delocalized pi systems, Diels-Alder cycloaddition
Class 6 Benzene and aromaticity Potential of pi electron systems, Hückel's rule
Class 7 Reactions of aromatic compounds Electrophilic aromatic substitution, Friedel-Crafts reaction
Class 8 Electrophilic attack on derivatives of benzene (1) Activation and deactivation of aromatic rings by substituents
Class 9 Electrophilic attack on derivatives of benzene (2) Activation and deactivation of aromatic rings by substituents, orientation of the attack
Class 10 Electrophilic attack on derivatives of benzene (3), Comprehension Test (2) Synthesis of substituted benzenes
Class 11 Aldehydes and ketones (1) Preparation and properties of carbonyl compounds
Class 12 Aldehydes and ketones (2) Addition of organometallic compounds to carbonyl compounds, protective groups of carbonyl groups
Class 13 Aldehydes and ketones (3) Wittig olefination
Class 14 Aldehydes and ketones (4) Baeyer-Villiger oxidation
Class 15 Enol and enolate, Comprehension Test (3) Enol tautomer, enolization

Textbook(s)

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)

Reference books, course materials, etc.

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)

Assessment criteria and methods

Students will be assessed on the concise exercise problems in each class (30%) and Comprehension Tests 1-3 (70%).

Related courses

  • Organic Chemistry I (alkanes and haloalkanes)
  • Organic Chemistry II (alcohols and alkenes)
  • Organic Chemistry IV (carbonyl compounds and amines)
  • Bioorganic Chemistry
  • Pharmaceutical Chemistry

Prerequisites (i.e., required knowledge, skills, courses, etc.)

No prerequisites

Other

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.

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