The main objectives of the course are knowlidges about terms of generall basic of organic chemistry, its nomenclature, relation between structure and reactivity, principles of synthesis of organic compounds. In the end of this course, the student will be able to understand the relationship between the structure of organic compound classes and their chemical reactivity.
Subject of organic chemistry in the context to other chemistry disciplines. Nomenclature principles. Geometry of carbon compounds. Bond types, their polarity and polarizability, energy, length. Molecular orbitals in basic organic compounds, electron distribution, electron, steric effects, intermolecular interaction, lipophility.
Chemical reactions as change of atom topology. Homo- and heterolysis of bonds. Reactive intermediates radicals, anions, cations and carbenes) and their stability. Classification of reagents. Hardness and softness of reagents. Charge- and orbital controlled reactions. Classification of organic reactions. Kinetic and thermodynamic aspect of reactivity. Selectivity of reactions, kinetic and thermodynamic controlled reactions.
Alkanes and cycloalkanes, nomenclature, isomerism, conformation, Newman projection. Stereoisomerism, E/Z, R/S nomenclature, Cahn-Ingold-Prelog rules. Reactivity-radical substitution, isomerization of alkanes, mechanism.
Alkenes, isomerism, reactivity. Addition reaction, mechanism and stereochemistry. Cycloadition reactions incl. Diels-Alder reactions. Polymerization of C=C monomers.
Dienes and polyenes, incl. terpenes. Types, structure and basic reactions. Kinetically and thermodynamically controlled reactions of dienes.
UV-VIS spectra and structure of organic compounds.
Alkynes, structure and reactivity. Basic reactions, synthesis.
The phenomenon of aromaticity and its properties. Nonbenzoid aromates (polycyclic aromates, annulenes, aromatic ions.} Mechanism of aromatic electrophilic substitution. Summary of electrophilic reactions, formation of electrophilic reagents. Effect of substituents on the reactivity and orientation. Hammet equation, sigma and rho constants. Ipso substitution. Nucleophilic substitution on the aromatic ring (SN1, SN2, elimination-addition mechanism). Conditions for addition reactions and reactions of oxidation. Substitution a other reactions on fused aromatic compounds.
Halogen derivatives. Influence of the carbon skeleton on the reactivity of halogen derivative. Mechanism of nucleophilic substitution, SN1, SN2, SNi mechanisms and their sterochemical course. 2. Elimination reactions, mechanisms E1, E2, E1cB and their stereochemical course. Substitution versus elimination. Alpha elimination reactions.
Hydroxy derivatives - alcohols and phenols. Reactivity of the hydroxy group, acidity and the influence of the carbon skeleton on it. Substitution and elimination reactions. Reactions on the carbon rest of the alcohol molecule. Oxidation reactions. Polyhydroxy derivatives.
Quinones, structure and chemical properties. Ethers, structure and nomenclature. Physical properties in comparison with alcohols. Typical chemical reactions of ethers (C-O bond cleavage, peroxides formation). Epoxides and cyclic ethers, their properties. Crown ethers and their application.
Thioles and sulfides. Comparison with the oxygen derivatives. Products of oxidation - sulfinic and sulfonic acids, sulfoxides and sulfones. Sulfonic acids and their derivatives, their preparation and reactivity, application.
Inorganic acid esters, their preparation and application. Amino derivatives and nomenclature. The basic chemical properties. Hofmann rearrangement. Reactivity of amines with nitrous acid. Diazotization and diazonium salts, coupling reactions. Amine oxides and their application. Enamines.
Quaternary ammonium salts. Hofmann elimination. Reactions with phase transfer catalysis. Diazocompounds. Diazoalkanes, diazoesters, diazoketones preparation and reactivity. Arndt-Eistert-Wolf rearrangement. Azides (Curtius and Schmidt rearrangement).
Nitro compounds. Structure and reactivity. Influence of the nitro group on the carbon skeleton. Preparation of nitro compounds. Ambident ions. Reduction of nitro compounds. Azo, azoxy and hydrazo compounds. Nitriles and isonitriles. Structure and reactivity and preparation. Hydrolysis of nitriles. Isonitrile test.
Organometallic compounds. Nomenclature. Relation between the metal and the chemical properties. Representatives of organometallic compounds, their reactivity and application in organic synthesis. Preparation.
Carbonyl derivatives. The phenomenon of carbonyl group. Aldehydes and ketones, nucleophilic addition reactions (reaction with oxygen, nitrogen, carbon and other nucleophiles. Influence of the carbonyl group on the carbon skeleton and application in organic synthesis. Summary of the name reactions. Oxidation and reduction.
Carbohydrates (aldoses, ketoses, trioses, tetroses, pentoses, hexoses), nomenclature. Mutarotation and cyclic form. Reactivity of the carbonyl and hydroxy groups. Products of oxidation and reduction, amino and deoxy derivatives. Disacharides (their structure and reductive properties). Polysacharides - homo and heteropolysacharides, representatives. Cellulose, its preparation and modification, application. Starch.
Carboxylic acids, their structure, representatives, chemical properties. Influence of the carbon rest on the acidity. Esterification. Function derivatives of carboxylic acids (esters, halogen derivatives, amides, anhydrides). Preparation and comparison of their properties. Application in organic synthesis. Lipids, their structure, properties. Waxes. Substituted derivatives of carboxylic acids (hydroxyacids,lactones, lactides, aminoacids, lactams, halogenacids, ketoacids).
Derivatives of carbonic acid, classification, their reactivity. Steroids. The structure of steroids, stereochemical aspects, numbering and nomenclature. Steroles (cholesterol), sex hormones (male - androsterone, testosterone, female - estrogens, progesterone), adrenocortical hormones, bile acids, cardiac poisons. Difference in their structure and activity.
Heterocyclic compounds. Structure and systematic nomenclature of heterocyclic compounds. Relation between the electronic structure and the chemical behaviour. Pyrrole, thiophene, furan, comparison of their chemical properties. Structure of pyrrole and bile pigments. Indole, indoxyl, indigo. Imidazole, pyrazole, thiazole, oxazole (the main chemical characteristic). Pyridine, structure and chemical properties. Pyridinium salts and pyridinium N-oxide. Quinoline and isoquinoline. Pyrylium salts, flavylium salts, coumarin and chromone, flavones - structure and their occurrence. Pyrazine, pyrimidine (bases of nucleic acids), pyridazine. Purines (the main representatives, bases of nucleic acids). Pterine (structure).
Principles and application of NMR spectroscopy.
Principles and application of IR spectroscopy.
Principles and application of mass spectroscopy.
Virtual Textbook of Organic Chemistry: http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/intro1.htm
SVOBODA, Jiří. Organická chemie. Vyd. 1. Praha: Vydavatelství VŠCHT, 2005. 310 s. ISBN 8070805617. info
POTÁČEK, Milan. Organická chemie : pro biology. 1. vyd. Brno: Vydavatelství Masarykovy univerzity, 1995. 208 s. ISBN 8021011254. info