SubjectsSubjects(version: 855)
Course, academic year 2019/2020
Organic Reactions Mechanisms - D110002
Title: Mechanismy organických reakcí
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2011
Semester: winter
Points: winter s.:0
E-Credits: winter s.:0
Examination process: winter s.:
Hours per week, examination: winter s.:0/0 other [hours/week]
Capacity: unknown / unknown (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
For type:  
Note: course is intended for doctoral students only
can be fulfilled in the future
Guarantor: Tobrman Tomáš doc. Ing. Ph.D.
Is interchangeable with: AP110002, P110002
Annotation -
Last update: Tobrman Tomáš doc. Ing. Ph.D. (10.04.2014)
The course is focused on an influence of reaction conditions on progress of organic reactions and prediction of organic reaction mechanism based on basic priciples of organic chemistry.
Aim of the course -
Last update: Tobrman Tomáš doc. Ing. Ph.D. (10.04.2014)

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: Tobrman Tomáš doc. Ing. Ph.D. (24.04.2014)

R: Grossman R.B., The Art of Writing Reasonable Organic Reaction Mechanisms, New York, Springer, 2003, 9780387954684

R: Edenborough M., Organic Reaction Mechanisms, Taylor & Francis Ltd, London, 1999, 0748406417

A: Carey F.A., Sundberg R.J., Advanced Organic Chemistry, Springer, New York, 9780387683461

A: Smith M.B., March J., March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, John Wiley & Sons, New Jersey, 9780471720911

Syllabus -
Last update: Tobrman Tomáš doc. Ing. Ph.D. (10.04.2014)

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

2. Electrophilic substitution on sp3 hybridized carbon atom. Synthetic use and examples.

3. Nucleophilic substitution on sp3 hybridized carbon atom. Influence of neighboring group, nucleophile and leaving group in the reaction outcome and mechanism. Synthetic use and examples.

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

5. Nucleophilic aromatic substitution. Meisenheimer complex. SNuAr of heteroaromatic compounds. Synthetic examples.

6. Radical substitutions.

7. Eliminations. Hoffmann rules. Stereochemistry of the reaction. Synthetic use and examples.

8. Electrophilic and nucleophilic additions. Application of the reaction in organic synthesis.

9. Diels- Alder type reaction. Sigmatropic rearrangement. Ene and electrocyclic reactions.

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

11. Oxidations and reductions.

12. Molecular rearrangements. Nucleophilic and electrophilic rearrangement.

13. Photochemical reactions

Registration requirements -
Last update: Tobrman Tomáš doc. Ing. Ph.D. (10.04.2014)

Organic Chemistry I, Organic Chemistry II

Course completion requirements -
Last update: Tobrman Tomáš doc. Ing. Ph.D. (24.04.2014)

It is compulsory to pass semestral tests and oral examination.

Coursework assessment
Form Significance
Continuous assessment of study performance and course -credit tests 50
Oral examination 50