Organic Chemistry I (Advanced Chemistry)

Numbering Code Year/Term 2021 ・ Second semester
Number of Credits 2 Course Type Lecture
Target Year Target Student
Language Japanese Day/Period Mon.1
Instructor name OOE KOUICHI (Graduate School of Engineering Professor)
MIURA TOMOYA (Graduate School of Engineering Associate Professor)
NAKAMURA MASAHARU (Institute for Chemical Research Professor)
Outline and Purpose of the Course Organic Chemistry I-IV are taught over two years (from the second half of sophomore year to the first half of senior year) as subjects that systematically instill students with the basics of organic chemistry they will need to know in order to work as researchers and engineers in all fields related to chemistry in the industrial, academic, and public sectors. Among these subjects, Organic Chemistry I allows students to understand ideas of acids and bases, as well as concepts of delocalization and conjugation of electronic states in compounds and intermediates, while also teaching them about reactions involving carbonyl groups from the standpoint of molecular orbital theory. In addition, students are taught how to determine the structure of organic compounds by making full use of various spectral methods.
Course Goals The goal is to understand organic reactions in a unified manner by considering mechanical similarities, rather than through mechanical memorization.
Schedule and Contents Structure of molecules and method of expressing organic reactions (Chapter 4 and Chapter 5), 1 session
Atomic orbitals and molecular orbitals are explained to students to provide a deeper understanding of the relationship between the shape of organic molecules and electronic structures. In addition, students learn to depict the movement of electrons in organic reactions using curved arrows.

Nucleophilic addition reactions to carbonyl groups (Chapter 6), 2 sessions
Students are given an overview of reaction modes between carbonyl groups and nucleophiles.

Delocalization and conjugation (Chapter 7), 2 sessions
The concepts of “delocalization and conjugation,” which are important for understanding differences in reactivity and physical properties of organic molecules, are explained using molecular orbital theory. In addition, aromaticity is explained.

Acidity and basicity (Chapter 8), 2 sessions
Students develop an understanding of the structural characteristics of compounds related to acidity and basicity, and learn how to calculate and use pH and pKa. In addition, equilibrium theory and changes in the electronic structure of compounds in proton transfer reactions are explained. During the session, an examination is conducted to confirm how much students have learned to date.

Organometallic reagents for carbon-carbon bond formation (Chapter 9), 1 session
The method for preparing organometallic compounds and examples of carbon-carbon bond forming reactions that use organometallic compounds are explained.

Nucleophilic substitution reactions on the carbon in carbonyl groups (Chapter 10), 2 sessions
By showing examples of substitution reactions that occur on the carbon in carbonyl groups, students are able to gain an understanding about the reactivity of carbonyl compounds based on reaction mechanisms that go through tetrahedral intermediates and the properties of nucleophiles and leaving groups. Using such examples also allows synthesis reactions that involve carbonyl compounds to be explained in a systematic manner.

Nucleophilic substitution reactions at C=O, following loss of carbonyl oxygen (Chapter 11), 2 sessions
The mechanisms behind the formation of acetals, imines, and alkenes from carbonyl compounds and their applications in synthetic chemistry are explained.

How to determine the structure of organic compounds (Chapter 3 and Chapter 13), 2 sessions
Students are explained the principles and characteristics of infrared spectroscopy and nuclear magnetic resonance spectroscopy, and are taught for determining the structure of organic compounds by reading various spectra.

Feedback lecture, 1 session
The fourteen lectures and examination contents are explained to students to improve their degree of learning (details are given during the lecture or on KULASIS). [All professors]
Evaluation Methods and Policy [Evaluation method]
Marks from (mid-term and end-of-term) examinations (90%); evaluation of performance in teaching sessions (10%)
Performance in teaching sessions is evaluated based on participation in sessions and the assessment of reports assigned in each teaching session.
[Evaluation policy]
Students must obtain a total of at least 60 (out of 100 marks) from the results of their (mid-term and end-of-term) examinations and their performance in teaching sessions.
60 marks or more: Pass
59 marks or less: Fail
Course Requirements None
Study outside of Class (preparation and review) Students should briefly glance over the handouts and textbook, and prepare for the contents of each unit before attending any lecture. In addition, students will actively work on report assignments given in each teaching session, while deepening their understanding of the contents of each unit. It would also be advisable for students to devote twice the amount of time spent in teaching session to review the material and prepare for the next session.
Textbooks Textbooks/References Organic Chemistry, 2nd Ed., Clayden, J., Greeves, N., Warren S., (Oxford University Press, 2012), ISBN:9780199270293
References, etc. McMurry Organic Chemistry, McMurry, J. (translated by Shibasaki, M., Iwasawa, N., Owada, T., Mashino, T.,), (Tokyo Kagaku Dojin), ISBN:9784807906918
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