Ch4_3P1P Organic Chemistry

Faculty of Education
Autumn 2001
Extent and Intensity
2/0/0. 3 credit(s). Type of Completion: zk (examination).
Teacher(s)
Mgr. Jiří Šibor, Ph.D. (lecturer)
Guaranteed by
Mgr. Jiří Šibor, Ph.D.
Department of Physics, Chemistry and Vocational Education – Faculty of Education
Contact Person: Alena Vozdecká
Prerequisites (in Czech)
Ch4_2p1p General Chemistry && Ch4_1P1L Laboratory Technics
Course Enrolment Limitations
The course is only offered to the students of the study fields the course is directly associated with.
fields of study / plans the course is directly associated with
Course objectives
The subject of organic chemistry. Nomenclature of organic chemistry. Principles of organic chemistry. General criteria of chemical reaction. Spectral properties of organic compounds. Alkanes and cycloalkanes. Optical activity and symmetry of molecules. Alkenes. Dienes and polyenes. Isoprenoides. Steroids. Pericyclic reactions. Alkynes. Aromatic compounds. Halogen derivatives. Hydroxy derivatives - alcohols and phenols. Ethers. Thioles and sulfides. Inorganic acid esters. Nitro compounds. Amino derivatives. Diazocompounds. Nitriles and isonitriles. Carbonyl derivatives. Carbohydrates. Carboxylic acids and their derivatives. Derivatives of carbonic acids. Lipids. Heterocyclic compounds.
Syllabus
  • The subject of organic chemistry. Nomenclature of organic chemistry. Name of compounds formation. Chemical bonds and bonding in organic molecules. Hybridization of the carbon atom, bonding energy, bond length, polarity of the chemical bond. Inductive and mesomeric effects, conjugation. Steric effects. General criteria of chemical reaction - reaction kinetics, reaction profiles and mechanism. Activation energy and enthalpy of the reaction. Chemical. Acidity and basicity. Arrhenius, Brønsted and Lewis explanation, acids and bases, pKa and pH. Spectral properties of organic compounds. Electronic spectra. Infrared spectroscopy, Nuclear magmetic resonance, mass spectroscopy. Alkanes and cycloalkanes. Chain isomerie, conformation analysis of alkanes and cycloalkanes. Fused cyclic systems. Newmann projection. cis-trans- Isomerism of cycloalkanes. Radical reactions as typical reactions of this system. Summary of radical reactions. Optical activity and symmetry of molecules. Chiral molecules, conditions of chirality. Methods of space objects presentation. Enantiomers, optical activity, specific rotation and its measurement, optical purity, racemic mixture. Molecules with more than one stereocenter. Cahn, Ingold, Prelog rules. Alkenes, stereochemistry of double bond, cis-trans and E-Z nomenclature. Addition reactions, their summary with attention to the stereochemistry and mechanism. Polymerizations. Dienes and polyenes (cumulated, isolated, conjugated). Reactions of conjugated dienes, conditions and mechanism of 1,2- and 1,4-addition. Isoprenoides (monoterpenes, sesquiterpenes, di-, tri- and tetraterpenes, carotenes). Steroids. Pericyclic reactions - electrocyclic reactions, cycloaddition reactions, the rules of their realization, sigmatropic rearrangements. Alkynes and their structure. Properties of the triple bond, addition reactions (electrophilic and nucleophilic additions), acidity of the hydrogen atoms bound on sp- carbon. Aromatic compounds.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, mechanisms and their sterochemical course. Elimination reactions, mechanism and their stereochemical course. Substitution versus elimination. Alfa elimination reactions. Hydroxy derivatives - alcohols and phenols. Reactivity of the hydroxy group, acidity and an 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. 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. 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. Nitro compounds. Structure and reactivity. Influence of the nitro group on the carbon skeleton. Preparation of nitro compounds. Ambident ions. Reduction of nitro compounds. Amino derivatives. 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 amonium salts. Hofmann elimination. Diazocompounds. Diazoalkanes, diazoesters, diazoketones preparation and reactivity. Azides. Azo, azoxy and hydrazo compounds. Nitriles and isonitriles. Structure and reactivity and preparation. Hydrolysis of nitriles. Isonitrile test. Organo metallic compounds. Relation between the metal and the chemical properties. Representatives of organometallic compounds, reactivity and application. Preparation. Carbonyl derivatives. The phenomenon of carbonyl group. Aldehydes and ketones, nucleophilic addition reactions. Influence of the carbonyl group on the carbon skeleton and application in organic synthesis. 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. Substituted derivatives of carboxylic acids (hydroxyacids,lactones, lactides, aminoacids, lactams, halogenacids, ketoacids). Derivatives of carbonic acid, classification, their reactivity. Lipids, their structure, properties. Waxes. 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 occuarance. Pyrazine, pyrimidine (bases of nucleic acids,pyridazine.Purines (the main representatives, bases of nucleic acids).Pterine (structure).
Literature
  • MCMURRY, John. Fundamentals of organic chemistry. 4th ed. Pacific Grove: Brooks/Cole publishing company, 1998, xxii, 566,. ISBN 0-534-35245-4. info
  • SOLOMONS, T. W. Graham. Organic chemistry. 6th ed. New York: John Wiley & Sons, 1996, xxvii, 121. ISBN 0471013420. info
  • HRNČIAR, Pavol. Organická chémia. 3., preprac. vyd. Bratislava: Slovenské pedagogické nakladateľstvo, 1990, 708 s. ISBN 8008000287. info
  • ČERVINKA, Otakar. Chemie organických sloučenin. Vyd. 1. Praha: Státní nakladatelství technické literatury, 1987, 1052 s. info
  • ČERVINKA, Otakar, Václav DĚDEK and Miloslav FERLES. Organická chemie. 2., přeprac. vyd. Praha: Státní nakladatelství technické literatury, 1980, 791 s. info
  • ČERVINKA, Otakar. Mechanismy organických reakcí. Vyd. 1. Praha: Státní nakladatelství technické literatury, 1976, 483 s. info
Assessment methods (in Czech)
Typ výuky: přednáška
Language of instruction
Czech
Further comments (probably available only in Czech)
The course is taught annually.
The course is taught: every week.
The course is also listed under the following terms Autumn 1999, Autumn 2000, Autumn 2002, Autumn 2003.
  • Enrolment Statistics (Autumn 2001, recent)
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