Course objectives |
Acquisition of basic knowledge of modern organic chemistry, understanding the structure and properties of organic compounds, nomenclature of organic compounds, the types of isomers, spectroscopic techniques in determining organic structures, understanding the mechanisms of organic reactions of addition, substitution, elimination and rearrangement. |
Learning outcomes expected at the level of the course (4 to 10 learning outcomes) |
After passing the course, students will be able to:
- describe the basic concepts, nomenclature of organic compounds, stereochemistry, and typical organic reactions of addition, elimination, substitution and rearrangement
- illustrate modes of applying the nomenclature, isomerism, stereochemistry and mechanisms of organic reactions (ion type and radical type)
- determine the structure of simple organic compounds on the basis of spectroscopic methods
- propose mechanisms for nucleophilic substitution reactions at saturated carbon and elimination reactions, additions to the unsaturated carbon and electrophilic aromatic substitution, taking into account the regio-selectivity / specificity and stereo-selectivity / specificity
- choose the correct chemical approach to solving problems in the field of organic chemistry, starting from the acquired knowledge in general, analytical and physical chemistry |
Course content broken down in detail by weekly class schedule (syllabus) |
Introduction. A short historical overview. The modern organic chemistry. The binding in organic molecules. Electronegativity and bond types. Quantum mechanics and atomic orbitals. Electronic configuration. Lengths and bond energies. (3 hours); Hybrid atomic orbitals (sp3, sp2 and sp). Molecular orbitals (σ- and π-bonds), polar and non-polar covalent bond. Bonding angles. Examples of organic molecules (orbital images) with single, double and triple bond. (3 hours); Physical properties, molecular structure and intermolecular bonds (dipole-dipole, van der Waals and hydrogen bonding). Solubility in organic solvent. Examples. Presentation of organic structures. (3 hours)
Classification and nomenclature of organic compounds. Functional groups and priority order. Alkanes. Alkenes. Alkynes. Aromatic hydrocarbons. Examples of the nomenclature of branched acyclic and cyclic and aromatic hydrocarbons. Alcohols. Phenols. Thiols. (3 hours); Ethers. Thioethers. Amines. Organohalogen compounds. Aldehydes. Ketones. Carboxylic acids. Carboxylic acid derivatives (acyl halides, anhydrides, esters, amides and nitriles). (3 hours); Examples of the nomenclature of various functional groups. (3 hours)
Isomers. Constitutional isomers. Index of hydrogen deficiency (IHD). The conformation and configuration. Stereoisomers. Conformations of acyclic alkanes (conformational analysis). (3 hours); Conformations of cycloalkanes (angle tension and heat of combustion). Substituted cycloalkanes. Geometric isomers of alkenes, aldoximes, ketoximes and azo compounds (cis, trans, E, Z, sin, anti). CIP rule sequence. (3 hours); Examples of geometric isomers of molecules with multiple double bonds. Geometric isomers of cyclic compounds (cis, trans isomers conformational structure). Symmetry, chirality and achirality. Stereogenic center (chiral center). Enantiomers. Diastereomers. (3 hours); The absolute configuration. CIP system - rule sequences. Fischer projection formula. The properties of the enantiomers. Optical activity. The racemic mixture. Enantiomeric excess. The optical purity. The biological significance of chirality. Examples of chiral biologically active substances. (3 hours); The separation of the racemate (direct crystallization, converting into diastereomers, chromatographic methods and kinetic resolution). Molecules having multiple stereogenic centers. Relative configuration erythro- and threo. Meso compounds. Stereoisomers of cyclic compounds. Chiral molecules without tetrahedral atoms. Examples of different kinds of stereoisomers. (3 hours)
Determination of organic structures. Introduction. Mass spectrometry (MS). Resolution. The molecular ion. Isotopes. Fragmentation. Examples of mass spectra. Electromagnetic radiation. Ultraviolet and visible spectroscopy (UV / Vis). Infrared spectroscopy (IR). Nuclear magnetic resonance (NMR). 13C NMR. 1H NMR. Chemical shift. Spin-spin coupling. Examples of the IR and NMR spectra. (11 hours)
Types of organic reactions. Mechanisms. Acid-base reactions. Nucleophiles and electrophiles. Redox reactions. Energy and reaction kinetics. (4 hours)
Nucleophilic substitution at saturated carbon. SN2-mechanism. SN1-mechanism. Energy diagrams. The stereochemistry of the nucleophilic substitution. (3 hours); Variables in the nucleophilic substitution of (leaving group, nucleophile, position of substitution and solvent). Conditions of SN2 and SN1-reaction. Competitive reactions. (3 hours); Nucleophilic substitution possibilities, conventional nucleophiles and their products. Examples. Elimination reactions. E1 and E2 mechanism. Conditions of E1 and E2 reactions. Orientation of elimination. The stereochemistry of the elimination (anti- or sin-) (3 hours); Competition elimination and substitution (reaction process conditions and examples). Examples of elimination reactions: dehydrogen-halogenation, dehalogenation of vicinal dihalogenalkanes, double dehydrogenation, dehydratation of alcohols (E1 and E2 mechanism, energy diagrams). (3 hours)
Electrophilic Addition. Orientation and additions (regioselectivity). The stereochemistry of the addition (anti- or sin-). Addition of free radicals. The addition of hydrogen. The addition of halogen. Halohydrin reaction. The addition of hydrogen halide. Conditions of Markovnikov and anti-Markovnikov addition. (3 hours); Hydration. Oxymercuration / demercuration. Hydroboration. Epoxidation - hydroxylation. Oxidation of alkenes with KMnO4 and OsO4. The ozonolysis of alkenes. The addition of alkenes (alkylation). (3 hours); Polymerization (radicals type and ions type). Examples of typical polymers. The additions to alkynes. Examples. Summary of the reaction of alkanes, alkenes, alkynes and halogenoalkanes. (3 hours)
Aromatic compounds and antiaromatics. The structure of benzene. Examples. Mechanism of electrophilic aromatic substitution. The impact on the groups on electrophilic aromatic substitution. (3 hours); Multiple substitutions of substituted aromatic compounds. Arenes. Phenols. Aromatic amines. Examples. (3 hours) |
