2019 Organic Chemistry IV (carbonyl compounds and amines)

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Academic unit or major
Undergraduate major in Life Science and Technology
Instructor(s)
Matsuda Tomoko  Urabe Hirokazu  Hata Takeshi 
Course component(s)
Lecture
Day/Period(Room No.)
Tue5-6(H121)  Fri5-6(H121)  
Group
-
Course number
LST.A217
Credits
2
Academic year
2019
Offered quarter
4Q
Syllabus updated
2019/3/18
Lecture notes updated
-
Language used
Japanese
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Course description and aims

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.

Student learning outcomes

By the end of this course, students will be able to:

1. Understand the chemistry of enols, enolates, and aldol condensation.
2. Understand the property and reaction of carboxylic acids and their derivatives.
3. Understand the property and reaction of amines and their derivatives.
4. Understand the reactivity of benzene substituents.
5. Understand the chemistry of ester enolates and Claisen condensation.

Keywords

Enol, aldol condensation, carboxylic acid, amine, reactivity of benzene substituents, Claisen condensation  

Competencies that will be developed

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

Class flow

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

  Course schedule Required learning
Class 1 Enols, enolates, aldol condensation enols, enolate ions, keto-enol equilibrium, halogenation and alkylation of aldehydes and ketones, aldol condensation
Class 2 Conjugate addition reaction property and conjugate addition of unsaturated aldehydes and ketones, conjugate addition reaction of enolate ions
Class 3 Carboxylic acids nomenclature, property and synthesis of carboxylic acids
Class 4 Property and reaction of the carboxylic acid derivatives acyl halides, acid anhydrides, ester, amides, reduction of carboxylic acids, bioactivity of carboxylic acids
Class 5 Review and exercise of classes 1〜4 comprehensive understanding of classes 1〜4 and contents of organic chemistry I-III
Class 6 Comparison of the carboxylic acid derivatives relative reactivity of the carboxylic acid derivatives, chemistry of acyl halides and the carboxylic acid anhydrides
Class 7 Amides amides, Hofmann rearrangement, alkanenitriles
Class 8 Property of amines nomenclature, structure and property of amines
Class 9 Synthesis and reaction of amines synthesis of amines, Hofmann elimination, Mannich reaction, nitrosation
Class 10 Review and exercise of classes 5〜9 comprehensive understanding of classes 6〜9, earlier classes and contents of organic chemistry I-III
Class 11 Reactivity of the benzene substituents benzylic position, phenols
Class 12 Reaction of benzene derivatives Claisen rearrangement, oxidation of phenols, biological oxidation and reduction
Class 13 Ester enolates and the Claisen condensation ester enolates, reaction of beta-dicarbonyl compound enolates and Claisen condensation
Class 14 Active methylene compounds Michael addition, synthesis of alpha-hydroxyl ketones
Class 15 Review and exercise of classes 11〜14 comprehensive understanding of classes 11〜14, earlier classes and contents of organic chemistry I-III

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 the final exam (70%).

Related courses

  • LST.A202 : Organic Chemistry I (alkanes and haloalkanes)
  • LST.A207 : Organic Chemistry II (alcohols and alkenes)
  • LST.A212 : Organic Chemistry III (benzene and ketones)
  • LST.A333 : Bioorganic Chemistry
  • LST.A343 : Pharmaceutical Chemistry
  • LST.A343 : 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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