SubjectsSubjects(version: 901)
Course, academic year 2021/2022
  
Organic Reaction Mechanisms - M110006
Title: Mechanismy organických reakcí
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2021 to 2021
Semester: winter
Points: winter s.:5
E-Credits: winter s.:5
Examination process: winter s.:
Hours per week, examination: winter s.:2/2 C+Ex [hours/week]
Capacity: 25 / 25 (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
Level:  
For type: Master's (post-Bachelor)
Note: course can be enrolled in outside the study plan
enabled for web enrollment
Guarantor: Kovaříček Petr Ing. Ph.D.
Interchangeability : N110015
Is interchangeable with: N110015
This subject contains the following additional online materials
Annotation -
Last update: Fialová Jana (04.01.2018)
The course is focused on mechanistic interpretation of reactions and processes in organic chemistry and their application in prediction of reaction parameters, product composition and stereochemistry of synthetically useful organic reactions.
Aim of the course -
Last update: Fialová Jana (04.01.2018)

Students will be able to:

understand the mechanisms of substitution, elimination and addition reactions.

predict the course of reactions.

suggest suitable mechanism of novel organic reaction.

Literature -
Last update: Kovaříček Petr Ing. Ph.D. (11.02.2022)

R. B. Grossman, The Art of Writing Reasonable Organic Reaction Mechanisms, Springer, Berlin 2006. 978-0-387-21545-7

F. A. Carey & Richard J. Sundberg, Advanced Organic Chemistry - Part A: Structure and Mechanisms, Springer, Boston, MA 2007. 978-0-387-44899-2

O. Cervinka a kol., Mechanizmy organickych reakci, SNTL/ ALFA, Praha 1981. 0463281

Learning resources -
Last update: Kovaříček Petr Ing. Ph.D. (11.02.2022)

The e=learning portal contains all slides from lectures as well as additional information sources and animations.

Syllabus -
Last update: Fialová Jana (04.01.2018)

1. General terms. Structural and electronic effects influencing a reaction course. Transition state theory.

2. Electrophilic substitution on sp3 hybridized carbon atom. Molecularity of the chemical reaction. Synthetic use and examples.

3. Nucleophilic substitution on sp3 hybridized carbon atom. Molecularity of chemical the reaction. Synthetic use and examples. Neighboring group participation in the reaction outcome and mechanism. Qualitative and quantitative evaluation of the nucleophiles and leaving groups.

4. Electrophilic aromatic substitution. Molecularity of the chemical reaction. Synthetic use and examples. Evaluation of substituents on aromatic systems and their influence on the reaction course.

5. Nucleophilic aromatic substitution. Meisenheimer complex.

6. Radical substitutions.

7. Eliminations. Zaitsev and Hoffmann rules. Regioselectivity of the reaction.

8. Additions. Steric effects and their influence on the reaction course. Application of the reaction in organic synthesis.

9. Diels- Alder type reaction. Cyclo-additions. Synthetic examples.

10. Nucleophilic additions on polarized bonds. Reaction of carbonyl compounds with organometalic reagents.

11. Oxidations and reductions.

12. Molecular rearrangements. Wagner- Meerwein rearrangements.

13. Photochemical reactions

Registration requirements -
Last update: Kundrát Ondřej Ing. Ph.D. (08.01.2018)

No.

Course completion requirements - Czech
Last update: Kovaříček Petr Ing. Ph.D. (19.02.2022)

Úspěšné absolvování zápočtových testů, prezantace miniprojektu na semináři a absolvování zkoušky.

Teaching methods
Activity Credits Hours
Konzultace s vyučujícími 0,5 14
Účast na přednáškách 1 28
Příprava na přednášky, semináře, laboratoře, exkurzi nebo praxi 1 28
Příprava na zkoušku a její absolvování 1,5 42
Účast na seminářích 1 28
5 / 5 140 / 140
 
VŠCHT Praha