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.
Recommended optional programme components
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
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
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.
Type of course unit
26 hours, optionally
Teacher / Lecturer