Course detail

Selected chapters from organic chemistry

FCH-BC_VODAcad. year: 2019/2020

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.

Learning outcomes of the course unit

By passing this subject the student acquires comprehensive knowledge enriched with selected chapters of Organic Chemistry. They are acquainted with C-C binding formation, selective reactivity of aromatic and heteoroatomic compounds, and acquire complex knowledge about protecting functional groups. This knowledge enables a wide range of applications in both the academic and industrial spheres.

Prerequisites

Organic chemistry

Co-requisites

Not applicable.

Recommended optional programme components

Not applicable.

Recommended or required reading

Organic chemistry, Solomons, T.W. Graham, Wiley 1980 a další vyd. (CS)
Organic Chemistry, Jonathan Clayden, Oxford, 2012 (CS)

Planned learning activities and teaching methods

The course uses teaching methods in form of Lecture - 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

Graded course credit - Final classification is based on average classification of individual tasks. Grades: A: 100 to 81 points, B: 80-71 points, C: 70-61 points, D: 60-59 points, E: 50 to 41 points, F: 40 points or less

Language of instruction

Czech

Work placements

Not applicable.

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

12th week: Basic principles of chemical structure identification

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.

Classification of course in study plans

  • Programme BKCP_CHTOŽP Bachelor's, 3. year of study, winter semester, 3 credits, compulsory-optional
  • Programme BPCP_CHTOZP Bachelor's, 3. year of study, winter semester, 3 credits, compulsory-optional

Type of course unit

 

Lecture

26 hours, optionally

Teacher / Lecturer