COURSE OBJECTIVE:
The main goal of the course is to acquaint students with the basic principles of modern organic chemistry, understanding the relationship between the structure and action of organic compounds and the application of methods of synthesis of organic compounds in biosciences and industry.
COURSE IMPLEMENTATION PROGRAM:
1. CARBON COMPOUNDS AND INTRODUCTION TO THE STRUCTURAL THEORY OF ORGANIC CHEMISTRY: introduction to the structural theory: empirical and structural molecular formulas, isomers, tetrahedral structure of methane; chemical bonds: octet rule, ionic and covalent compounds, Lewis structures, resonance; quantum mechanics (Schrödinger wave equation), atomic and molecular orbitals; methane and ethane structure: sp3-hybridization; ethene structure: sp2-hybridization, cis-trans isomerism; ethyne structure: sp-hybridization.
Examples of problems for determining the structures of isomers, covalent and ionic bonds in a molecule, Lewis structures, resonance structures.
2. INTRODUCTION TO ORGANIC REACTIONS: ACIDS AND BASES: Types of chemical reactions and their mechanisms; acid-base reactions, Brönsted, Lowry and Lewis definition of acids and bases; heterolysis of carbon bonds (carbocations and carbanions), strength of acids and bases, ratio of structure and action of acids, acidity of carboxylic acids, organic compounds as bases; introduction to the mechanisms of organic reactions.
Examples of tasks of acid-base reactions, recognition of acids and bases in reactions and acidity of given compounds.
3. CLASSES OF CARBON COMPOUNDS, FUNCTIONAL GROUPS: Hydrocarbons: alkanes, alkenes, alkynes and aromatic compounds; polar covalent bonds, polar and non-polar molecules, functional groups in organic molecules, alkyl halides, alcohols, ethers, amines, aldehydes and ketones, carboxylic acids, esters and amides, nitriles. Relationship between structure and physical properties of molecules (hydrogen bonds, van der Waals forces).
Examples of tasks for defining functional groups and associated classes of compounds, naming representatives of classes of carbon compounds.
4. ALKANES - CONFORMATIONAL ANALYSIS AND INTRODUCTION TO SYNTHESIS: Conformational analysis of alkanes, relative stability of cycloalkanes-ring tension, cis- and trans-isomerism of cycloalkanes, synthesis of alkanes and cycloalkanes, planning of organic synthesis-retrosynthetic analysis (synthones, functional groups and topological strategies), examples of synthesis of biologically and pharmacologically significant molecules based on retrosynthetic analysis.
Examples of tasks for determining the conformation of individual alkanes, cis- and trans-isomerism of cycloalkanes.
5. STEREOCHEMISTRY AND CHIRALITY I: biological significance of chirality; isomerism: constitutional isomers and stereoisomers; chiral molecules and enantiomers, nomenclature of enantiomers (Cahn-Ingold-Prelog system of rules R, S), relative and absolute configuration, optical activity of enantiomers, molecules with multiple centers of chirality, meso-compounds, Fischer projection formulas, stereoisomerism of cyclic compounds.
Examples of tasks for determining the relative and absolute configuration of compounds with a single center of chirality.
6. STEREOCHEMISTRY AND CHIRALITY II: Heteroatoms as centers of chirality, axial chirality (atropisomerism), helicity (winding), homochirality in nature, pseudochirality, prochirality, diastereoisomerism, preparation of enantiomerically pure compounds (fractional crystallization by racemate chromatography, chiral drugs: drug-receptor enantiomer-receptor interaction.
Examples of tasks for determining the relative and absolute configuration of compounds with multiple centers of chirality.
7. IONIC REACTIONS - NUCLEOPHILIC SUBSTITUTION REACTIONS OF ALKYL-HALOGENIDES: Nucleophilic substitution reactions: nucleophiles, leaving groups; kinetics, mechanism and stereochemistry of the SN2 and SN1 reactions (carbocations); examples of organic syntheses by transformation of functional groups by means of SN2 reactions.
Examples of tasks for nucleophilic substitution reactions of alkyl halides.
8. IONIC REACTIONS - ELIMINATION REACTIONS OF ALKYL-HALOGENIDES: influence of nucleophiles on competitive elimination and substitution reactions; mechanism of E1 and E2 reactions, stereoselectivity and regioselectivity of E1 reactions, stereospecificity of E2 reactions of substituted cyclohexanes, regioselectivity in elimination reactions (Hoffmann and Zaitsev's rule), carbanionic mechanism of elimination reactions (E1cB).
Examples of tasks for elimination reactions of alkyl halides.
9. ALKENES AND ALKINES I: PROPERTIES AND SYNTHESIS: determination of the configuration of E- and Z-diastereoisomers, relative stability of alkenes, cycloalkenes, synthesis of alkenes by dehydrohalogenation of alkyl halides and dehydration of alcohols, stability of carbocations and alkali metal molecular reactions and replacing the acidic hydrogen atoms of the terminal alkynes.
Examples of tasks in the synthesis of alkene and alkyne and the determination of the E- and Z-configuration.
10. ALKENES AND ALKINES II: ADDITION REACTIONS: addition of hydrogen halides to alkenes (Markovnikov rule), stereochemistry of ionic addition reactions
10. ALKENES AND ALKINES II: ADDITION REACTIONS: addition of hydrogen halides to alkenes (Markovnikov rule), stereochemistry of ionic reactions of addition to alkenes, oxymercury and demercurization of alkenes (Markovnikov addition) of alcohol synthesis by hydroboration and marine oxidation , alkene hydroboration and alkyl-borane synthesis, halogen addition to alkenes, stereochemistry of halogen addition reactions to alkenes.
Examples of problems for addition reactions.
11. 13C one- and two-dimensional nuclear magnetic resonance spectroscopy (1D and 2D-NMR), application of nuclear magnetic resonance in medicine; introduction to mass spectrometry, ionization and fragmentation of molecular ion, determination of molecular formula and mass, application of mass spectrometry in biomedicine.
Examples of tasks in determining structures using 1H NMR spectra and mass spectra of compounds.
12. RADICAL REACTIONS: energies of homolytic cleavage of the bond and relative stability of radicals, selectivity in radical substitution reactions, chlorination of methane-activation energy, halogenation of higher alkanes, geometry of alkyl radicals, radical additions to alkenes (anti-Markovnikov alkyl addition polymer , radicals in biology, medicine and industry.
Examples of tasks for radical reactions.
13. ALCOHOLS: synthesis of alkenes from alkenes, reactions of alcohols, alcohols as acids, conversion of alcohols to alkyl halides, mechanism of reaction of alcohols and hydrohalic acids and acetals, silyl ether-protecting groups of alcohols, sugar alcohols.
Examples of tasks for alcohol synthesis and reactions.
14. ETHERS: synthesis of ethers, silyl protecting groups in ethers, reactions of ethers (cleavage of ethers by strong acids), cyclic ethers (epoxides): synthesis by epoxidation of alkenes, Sharpless asymmetric epoxidation of alkenes; epoxy reactions (acid catalyzed ring opening, carcinogenicity of epoxides by biological oxidation, crown ethers: intermediate catalysts, transport of antibiotics and crown ethers.
Examples of tasks for the synthesis and reactions of ethers.
DEVELOPING GENERAL AND SPECIFIC COMPETENCIES OF STUDENTS
The main goal of student education is to master the principles of organic chemistry and methods of organic synthesis, and their application in the synthesis of new compounds.
Specific competencies: mastering the basic techniques of work in the synthesis of organic compounds and their identification.
STUDENTS' OBLIGATIONS:
Participation in lectures and exercises is mandatory. There will be a continuous test of knowledge during tests during the lecture, the result of which will depend on the exemption from the written part of the exam.
CONDITIONS FOR OBTAINING SIGNATURES
Regular class attendance
TEACHING METHODS:
Lectures and exercises
MANNER OF EXAMINATION OF KNOWLEDGE AND EXAMINATION
Three tests during the semester, written and oral exam.
METHOD OF MONITORING THE QUALITY AND PERFORMANCE OF COURSES
Student survey
WHICH COURSES STUDENTS MUST PASS IN ORDER TO FOLLOW THE ABOVE COURSE CONTENT
General and inorganic chemistry, analytical chemistry
COURSE LEARNING OUTCOMES:
1. analyze the structure of compounds with carbon, define organic compounds and the nature of chemical bonds in organic molecules based on the theory of molecular orbitals and hybrid atomic orbitals
2. define the basic types of organic reactions and explain the basic reaction mechanisms with the recognition of reactive intermediates of reactions,
3. label functional groups in molecules and define classes of compounds, apply IUPAC rules for naming organic compounds
4. explain the conformations of alkanes and cycloalkanes, define and name isomers
7. define basic synthesis reactions and reactions in which alkanes, alkenes, alkynes, alcohols, ethers participate, explain radical reactions
LEARNING OUTCOMES AT PROGRAM LEVEL:
1. knowledge and understanding of scientific principles important for chemistry and engineering of materials, especially in the field of chemistry
2. knowledge and understanding of the four basic elements of material chemistry and engineering: structure, properties, production and use of materials
3. skills required for work in the chemical and physical laboratory, use of laboratory equipment and work in the laboratory in a safe manner
4. ability to analyze materials using chemical and physical techniques and using instrumental methods of analysis
5. ability to identify, define and solve problems in the field of chemistry
TEACHING UNITS WITH ASSOCIATED LEARNING OUTCOMES AND EVALUATION CRITERIA:
Teaching unit:
1. Carbon compounds and chemical bonds, structural theory, atomic and molecular orbitals - hybridization
Learning outcomes:
- analyze the structure of carbon compounds, binding in organic molecules and the structure of molecules in space
- define resonant structures
- get acquainted with the concept of hybridization of carbon atoms: sp3, sp2 and sp hybridization and the type of bond between carbon atoms
Evaluation criteria:
- draw joints with ionic and covalent bonds, identify the bond angle
- determine the charge of the molecule
- draw Lewis structures of given joints
- draw resonant structures
Teaching unit:
2. Introduction to organic reactions, acid-base reactions, definitions of acids and bases; heterolysis of carbon bonds (carbocations and carbanions), introduction to the mechanisms of organic reactions
Learning outcomes:
- define acids and bases, strength of acids and bases, relationship between structure and action of acids
- recognize heterolytic cleavage of the bond and the formation of appropriate intermediates in such reactions
Evaluation criteria:
- recognize organic compounds as acids and bases
- apply the theory of acids and bases to specific organic compounds
- distinguish between homolytic and heterolytic cleavage of the bond and apply such cleavage to specific examples
Teaching unit:
3. Classes of compounds - functional groups
Learning outcomes:
- identify functional groups in molecules and define classes of compounds
- apply the IUPAC rules for the designation of organic compounds
Evaluation criteria:
- draw the structural formulas of organic compounds according to the system name of the compound and vice versa
- based on the structure recognized physical properties of molecules
Teaching unit:
4. Alkanes and cycloalkanes
Learning outcomes:
- explain the conformations of alkanes and cycloalkanes
- define energy changes and stability of alkanes
- understanding the relative stability of cycloalkanes
Evaluation criteria:
- draw conformations of alkanes and cycloalkanes
- determine energetically more favorable conformers
- draw conformational isomers with a wedge-shaped projection formula, Newman's formula
Teaching unit:
5. Stereochemistry and chirality
Learning outcomes:
- define and name constitutional isomers and stereoisomers
- understanding the biological significance of chirality
- define relative and absolute configuration (CIP rule)
- know the stereoisomers of cyclic compounds
Evaluation criteria:
- illustrate with examples of isomers
- identify chiral molecules, determine stereogenic centers and absolute configurations of molecules by applying CIP rules, meat-compounds
- draw stereoisomers with one or more stereogenic centers by Fischer projection formula
Teaching unit:
6. Ionic reactions
Learning outcomes:
- distinguish nucleophilic substitution reactions with respect to reaction kinetics, mechanism and stereochemistry
- define when these reactions take place in competition with elimination reactions
Evaluation criteria:
- draw product structures in substitution and elimination reactions
- illustrate by example the factors influencing the substitution reactions (SN1 and SN2) and elimination (E1 and E2)
Teaching unit:
7. Alkenes and alkynes
Learning outcomes:
- explain the structure of alkenes and alkynes and state the basic reactions of preparation from alkyl halides or alcohols
- understanding of reaction mechanisms and recognition of reactive intermediates of reactions
- explain the reaction of electrophilic addition in relation to the structure
Evaluation criteria:
- distinguish nucleophiles, electrophiles and free radicals, distinguish reactions of nucleophilic substitution, elimination (Zaitsev's and Hoffmann's rule), additions (Markovnikov's rule) and apply the mentioned reactions on concrete examples
- draw the structural formulas of the products in the reactions of alkyl halides, alcohols and alkenes with the definition of the stereochemistry of the reactions
Teaching unit:
8. Nuclear magnetic resonance (NMR) and mass spectrometry
Learning outcomes:
- explain the principle of nuclear magnetic resonance (NMR)
- define basic concepts (chemical shift, signal splitting, signal integration, proton shading) in NMR spectroscopy
- explain the principle of mass spectrometry
- define methods of ionization of organic compounds
Evaluation criteria:
- draw the structure of the organic compound according to the given 1 H NMR spectrum,
- assign protons in the 1 H NMR spectrum of a given compound
- state the fragmentation of the signal in the mass spectrum for the given compounds
Teaching unit:
9. Radical reactions
Learning outcomes:
- define radical reactions and relative stability of formed radicals
- explain multiple substitution in relation to selective radical reactions
- explain selectivity in radical substitution reactions
- define radical polymerization
Evaluation criteria:
- give examples of radical reactions with an explanation of the mechanism of these reactions
- distinguish the stability of structurally different radicals
- illustrate by example the stereochemistry of radical reactions
- illustrate by example radical polymerization
Teaching unit:
10. Alcohols and ethers
Learning outcomes:
- explain the physical properties of alcohol and ether
- knowledge of alcohol synthesis from alkene and carbonyl compounds
- knowledge of the most important reactions of ether production
- understanding the strategy of application of protection groups
- knowledge of alcohol and ether reactions
Evaluation criteria:
- illustrate with examples of alcohol synthesis from alkene, by oxido-reduction reaction, using organometallic compounds
- apply appropriate reagents in the synthesis of alcohols and ethers and their reactions
- apply appropriate alcohol protection groups
- state the methods of obtaining ether (Williamson synthesis, etc.)
- state the reactions of ether cleavage, epoxy ring opening with defining the mechanism and stereochemistry of the reaction
|
Pristupačnost
