Course detail

Selected Chapters of Organic Chemistry

FCH-MC_VOCHAcad. year: 2021/2022

Halogenated derivatives, nucleophilic substitution on saturated carbon atom, aromatic nucleophilic substitution reactions, elimination reactions. Alcohols, phenols, polyhydroxy compounds. Oxidation of alcohols and phenols. Ethers, peroxides, epoxides, crown ethers. Thiols, sulfides, sulfonic acids and their derivatives. Esters of mineral acids. Amines, diazotation, arendiazonium salts - use, amine oxides. Diazo compounds, carbenes. Azides. Nitro compounds. Organometallic compounds. Aldehydes and ketones, nucleophilic addition to the C = O group, aldolization reactions of aldehydes and ketones. Carboxylic acids, esterification, acyl halides, anhydrides, esters, amides. Halogen and amino acids, peptides, carbonic acid derivatives.

Language of instruction

Czech

Number of ECTS credits

4

Mode of study

Not applicable.

Learning outcomes of the course unit

The aim of the course is a detailed study of selected fragments of organic chemistry and organic synthesis. The lectures will discuss in detail the chemistry of functional groups and their transformation, as well as methods of protecting functional groups. Students will also be introduced to modern methods of C-C bond formation. The course will also focus on single and multistep syntheses, selective reactivity of aromatic and heteroaromatic. The structure of the course is designed so that after completing this discipline the students are well prepared for the study of other courses that immediately theoretically and practically follow up with this course.

Prerequisites

Organic chemistry

Co-requisites

Not applicable.

Planned learning activities and teaching methods

The course uses teaching methods in form of Lecture - 2 teaching hours per week, seminars - 2 teaching hours per week. The e-learning system (LMS Moodle) is available to teachers and students.

Assesment methods and criteria linked to learning outcomes

Credit: will be awarded on the basis of the student's active participation during the semester during the semester.
Exam: exam consists of oral part.

Course curriculum

1 week: Work with chemical literature: introduction to the study of chemical literature, primary, secondary and other sources. Work with patent literature. Database resources

2 weeks: Alkenes, Cis- and Trans-additions, overview of addition reactions, Alkynes, alkyne reactivity, AE, AN and AR addition reactions

Week 3: Aromatic hydrocarbons, Individual types of SEAr, Aromatic nucleophilic substitution of SNAr, Use of the decomposition of diazonium salts for the preparation of other derivatives

4th week: Halogenated derivatives, SN1, SN2 (kinetics and stereochemistry). Elimination of halogen on Csp3 - mechanism E1, E2, E1cB - region specificity (Zajcev rule), sterospecificity

5th week: Hydroxy compounds - alcohols and phenols. Reactivity of hydroxyl group, acidity and influence of carbonaceous residue on acidity level
Ethers, Typical chemical properties, C-O bond cleavage, peroxide compounds formation

6th week: Amino compounds, properties - basicity, nucleophilicity, Sandmeyer, Enamines, preparation and reactivity

Week 7: Methods of C-C bond formation
Reactions of organometallic compounds, Organolithne reagents - preparation and stability, basicity, Use of organometals in organic synthesis, Chemistry of magnesium and lithium compounds, Grignard reagents - preparation and properties, reactions with carbonyl derivatives, selectivity of Grignard reactions

Week 8: Methods of C-C bond formation: cross-coupling reactions
Reaction using compounds of palladium - Suzuki reaction, Stille reaction, Sonogashira reaction, Kumada reaction, Heck reaction

9-10. week: Methods of C-C bond formation
Aldolization of carbonyl compounds, aldolization and α-substitution, conjugated additions

11th week: Carboxylic acids, functional derivatives of carboxylic acids, esters, acidic basic hydrolysis, reesterification, preparation of amides from esters. Halides - preparation and reactivity, Hoffman degradation of amides

12-13th week: Basic principles of chemical structure identification

Work placements

Not applicable.

Aims

The aim is to build on the basic knowledge of the subjects Organic chemistry I and II and to focus more closely on selected chapters. Based on the already acquired knowledge from the previous chapters of Organic Chemistry, the problems of this subject will be focused on deepening the students' knowledge and abilities related to C-C binding, protection of functional groups, selective reactivity of aromatic and heteroaromatic compounds.

Specification of controlled education, way of implementation and compensation for absences

Attendance at the lectures is not compulsory, but due to the specific nature of the course it is recommended.

Recommended optional programme components

Not applicable.

Prerequisites and corequisites

Not applicable.

Basic literature

Organic Chemistry, Jonathan Clayden, Oxford, 2012 (EN)
Organic chemistry, Solomons, T.W. Graham, Wiley 1980 a další vyd. (EN)
Organická chemie, John McMurry, VUTIUM, 2015 (CS)

Recommended reading

Not applicable.

Elearning

Classification of course in study plans

  • Programme NPCP_CHTM Master's 1 year of study, winter semester, elective
    2 year of study, winter semester, elective
  • Programme NPCP_ECHT Master's 1 year of study, winter semester, compulsory-optional

  • Programme NPCP_CHMA Master's

    specialization BF , 1 year of study, winter semester, compulsory
    specialization CHBL , 1 year of study, winter semester, compulsory

  • Programme NPCP_CHTPO Master's

    specialization PCH , 1 year of study, winter semester, compulsory
    specialization CHPL , 1 year of study, winter semester, compulsory

  • Programme NKCP_CHTM Master's 1 year of study, winter semester, elective
    2 year of study, winter semester, elective

  • Programme NKCP_ECHT Master's

    specialization --- , 1 year of study, winter semester, compulsory-optional

  • Programme NKCP_CHTPO Master's

    specialization PCH , 1 year of study, winter semester, compulsory
    specialization CHPL , 1 year of study, winter semester, compulsory
    specialization BCH , 1 year of study, winter semester, compulsory

  • Programme NPCP_CHPL Master's 1 year of study, winter semester, compulsory
  • Programme NKCP_CHPL Master's 1 year of study, winter semester, compulsory

Type of course unit

 

Exercise

26 hod., compulsory

Teacher / Lecturer

Guided consultation in combined form of studies

26 hod., optionally

Teacher / Lecturer

Elearning