2022 | Organic Chemistry I (alkanes and haloalkanes)

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2022　Organic Chemistry I (alkanes and haloalkanes)

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Academic unit or major: Undergraduate major in Life Science and Technology

Instructor(s): Nakamura Hiroyuki Seio Kohji Mori Toshiaki Ohkubo Akihiro Matsuda Tomoko Tsutsumi Hiroshi

Class Format: Lecture (Livestream)

Media-enhanced courses

Day/Period(Room No.): Tue7-8(H1101) Fri7-8(H1101)

Group: -

Course number: LST.A202

Credits: 2

Academic year: 2022

Offered quarter: 1Q

Syllabus updated: 2022/3/16

Lecture notes updated: -

Language used: Japanese

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Syllabus

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. 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.

Keywords

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)

Competencies that will be developed

✔ Specialist skills

Intercultural skills

Communication 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. Three professors are responsible for this　online course.

Course schedule/Required learning

	Course schedule	Required learning
Class 1	Ionic and Covalent Bonds	Understand the Octet Rule, and accurately draw Lewis Structures and Resonance Forms.
Class 2	Hybrid Orbitals	Understand Atomic Orbitals, Molecular Orbitals, and Hybrid Orbitals, and explain covalent bonding.
Class 3	Acids and Bases	Explain Acid-Base Reactions, and Electrophile-Nucleophile Reactions in relation to each other.
Class 4	Structural and Physical Properties of Alkanes	Understand Naming and Conformation of Alkanes, explain Hyperconjugation, and the Radical Chain Mechanism.
Class 5	Comprehension Assignment (1)
Class 6	Names and Physical Properties of Cycloalkanes	Understand Ring Strain and accurately draw Structures of Cycloalkanes.
Class 7	Substituted Cyclohexane	Explain Conformation of Substituted cyclohexanes and Polycyclic Alkanes.
Class 8	Chiral Molecules	Understand　Optical Activity and Absolute Configuration (R-S Sequence Rules)，and accurately draw Fischer Projections.
Class 9	Stereochemistry in Chemical Reactions	Understand Racemic Mixtures and Enantiomers, and explain Separation of Enantiomers.
Class 10	Comprehension Assignment(2)
Class 11	Stereochemistry of the SN2 Reaction	Understand Frontside Attack and Backside Attack, and accurately draw SN2 Reaction Mechanism.
Class 12	Unimolecular Nucleophilic Substitution	Understand Effects of Solvent, Leaving Group, and Nucleophile on Unimolecular SN1 Nucleophilic Substitution, and accurately draw SN1 Reaction Mechanism.
Class 13	Unimolecular Elimination	Understand Competition Between Substitution and Elimination, and accurately draw E1 Reaction Mechanism.
Class 14	Bimolecular Elimination	Understand Competition Between Substitution and Elimination, and accurately draw E2 Reaction Mechanism.

Out-of-Class Study Time (Preparation and Review)

To enhance effective learning, students are encouraged to spend approximately 100 minutes preparing for class and another 100 minutes reviewing class content afterwards (including assignments) for each class.
They should do so by referring to textbooks and other course material.

Textbook(s)

Organic Chemistry - Structure and Function, 8th ed., K. P. C. Vollhardt and N, E. Schore, W. H. Freeman and Co., New York,; The Japanese translation, 8th ed., Kagakudojin, Kyoto (Japanese)

Reference books, course materials, etc.

Study Guide and Solutions - Manual for Organic Chemistry, N, E. Schore, W. H. Freeman and Co., New York

Assessment criteria and methods

The concise exercises in each class (30%) and three comprehension assignments (70%, Comprehension Assignment (3) will be held during the period of the quarter-end exams.).

Related courses

LST.A207 ： Organic Chemistry II (alcohols and alkenes)
LST.A212 ： Organic Chemistry III (benzene and ketones)
LST.A217 ： Organic Chemistry IV (carbonyl compounds and amines)
LST.A333 ： Bioorganic Chemistry
LST.A343 ： Pharmaceutical Chemistry

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

No prerequisites.

Contact information (e-mail and phone) Notice : Please replace from "[at]" to "@"(half-width character).

Tsutsumi htsutsum[at]bio.titech.ac.jp
Seio 　seio.k.aa[at]m.titech.ac.jp
Ohkubo 　ohkubo.a.aa[at]m.titech.ac.jp

Office hours

Contact in advance through email.

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.

TOKYO INSTITUTE OF TECHNOLOGY