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2018　Laboratory Course in Advanced Organic Chemistry

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Academic unit or major
Undergraduate major in Chemistry
Instructor(s)
Eguchi Tadashi  Suzuki Keisuke  Iwasawa Nobuharu  Goto Kei  Ohmori Ken  Kudo Fumitaka  Takaya Jun  Ando Yoshio  Sase Shohei  Miyanaga Akimasa  Takahashi Kohei 
Class Format
    
Media-enhanced courses
Day/Period(Room No.)
Tue5-8(南1号館化学コース実験室)  Fri5-8(南1号館化学コース実験室)  
Group
-
Course number
CHM.D305
Credits
2
Academic year
2018
Offered quarter
4Q
Syllabus updated
2018/3/20
Lecture notes updated
-
Language used
Japanese
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Course description and aims

In this course, students carry out advanced organic experiments by their hand to understand advanced organic chemistry that was learned in the class of Organic Chemistry II and Organic Chemistry III. They also learn the advanced operational methods for organic experiments and structural analysis of organic molecules. The experimental results are summarized and submitted as report for four times. We also discuss the experimental results to understand advanced organic chemistry in detail at the class of Exercise in Advanced Chemistry II in the same quarter.

Although students can learn advanced organic chemistry through lectures and reading textbooks, they also need to know the advanced operational methods for organic experiments to investigate real research in laboratory in Chemistry Department. To learn specific operations in organic experiments, they need to carry out the experiments by their hands. This course also supports students understand advanced organic chemistry that was learned from lectures and textbooks in detail.

Student learning outcomes

By the end of this course, students will be able to:
1) Perform advanced organic chemical experiments
2) Perform advanced structural analysis of organic compounds
3) Explain advanced experimental methods for organic chemical reactions and the experimental results
4) Adopt their advanced organic chemical knowledge that was learned from textbook to understand real organic chemical reactions

Keywords

Organic Experiments, Chemistry of Enolates, Benzoin Condensation, Stereochemical Problems, Carbocation Rearrangements, Claisen Rearrangement, Cross Coupling Reaction

Competencies that will be developed

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

Class flow

Students perform organic experiments in a laboratory room for Chemistry Students according to the course schedule. Students are required to learn outside of the classroom for preparation of the experimental flow and review purposes under the instructor's guidance.

Course schedule/Required learning

  Course schedule Required learning
Class 1 Chemistry of Enolates: Alkylation of Ethyl Acetoacetate (Perform the reaction) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 2 Chemistry of Enolates: Alkylation of Ethyl Acetoacetate (Purification of the reaction products, analysis of chemical properties and structural analsysis) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 3 Chemistry of Enolates: Synthesis of Six-membered Carbocyclic Compound from Ethyl Acetoacetate (Perform the reaction) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 4 Chemistry of Enolates: Synthesis of Six-membered Carbocyclic Compound from Ethyl Acetoacetate (Purification of the reaction products, analysis of chemical properties and structural analysis) Review the experiments and discuss the obtained results. Writing the experimental report. Preparation for the next experiment.
Class 5 Benzoin Condensation (Perform the reaction) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 6 Benzoin Condensation (Purification of the reaction products, analysis of chemical properties and structural analysis) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 7 Stereoselective Reduction of Carbonyl Group (Perform the reaction and Purification of the reaction products, analysis of chemical properties and structural analysis) Review the experiments and discuss the obtained results. Writing the experimental report. Preparation for the next experiment.
Class 8 Carbocation Rearrangements (Preparation of substrates) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 9 Carbocation Rearrangements (Perform the reaction) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 10 Carbocation Rearrangements (Purification of the reaction products, analysis of chemical properties and structural analysis) Review the experiments and discuss the obtained results. Writing the experimental report. Preparation for the next experiment.
Class 11 Claisen Rearrangement (Perform the reaction) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 12 Claisen Rearrangement (Purification of the reaction products, analysis of chemical properties and structural analysis) Review the experiments and discuss the obtained results. Preparation for the next experiment.
Class 13 Cross Coupling Reaction: Purification of the reaction products, analysis of chemical properties and structural analysis Review the experiments and discuss the obtained results. Writing the experimental report. Preparation for the next experiment.
Class 14 Discussion of Laboratory Course in Advanced Organic Chemistry Preparation of a report for Laboratory Course in Advanced Organic Chemistry
Class 15 Summary of this course and cleaning up laboratory room

Textbook(s)

Organic Experiments for Students in Department of Chemistry in TITECH (Organic Chemistry Laboratory)

Reference books, course materials, etc.

Organic Experiments (Fieser/Williamson), Organic Chemistry (K. P. C. Vollhardt and N. E. Schore)

Assessment criteria and methods

Exercise problems and performance in each experimental class (30%) and four reports for experiments (70%)

Related courses

  • CHM.D201 ： Organic Chemistry I
  • CHM.D202 ： Organic Chemistry II
  • CHM.D301 ： Organic Chemistry III
  • CHM.D203 ： Exercise in Organic Chemistry I
  • CHM.D204 ： Exercise in Organic Chemistry II
  • CHM.D205 ： Laboratory Course in Basic Organic Chemistry
  • ZUC.D330 ： Exercise in Advanced Chemistry II
  • CHM.D332 ： Structural Organic Chemistry
  • CHM.A201 ： Chemistry for Safety

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

No prerequisites are necessary, but enrollment in the related courses is desirable.

Office hours

Students may approach the instructors at the end of class or contact by e-mail in advance to schedule an appointment.

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