FC3008 Organic Chemistry

Faculty of Education
Autumn 2021
Extent and Intensity
3/0/0. 4 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: Jana Jachymiáková
Supplier department: Department of Physics, Chemistry and Vocational Education – Faculty of Education
Timetable
Tue 21. 9. to Tue 14. 12. Tue 9:00–11:50 učebna 7
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
(a) knowledge understand and explain the basic relationships between the structure and reactivity of hydrocarbons and their derivatives; use information to solve independently the problems of hydrocarbon derivatization; b) Skills based on acquired knowledge to derive products of unknown reactions; to interpret the characteristics of groups of organic and selected bioorganic compounds. c) attitudes To gain general and professional insight and ability to apply acquired knowledge and skills in teaching practice
Learning outcomes
At the end of this course, student should be able to: understand and be able to explains structure and reactivity basic relationships of organic compounds; use data to organic chemistry problem solutions independently; make reasoned decisions about organic compounds reactivity; formulate a reasoned differential diagnosis for products deduction of similar reactions; interpret characteristics of organic componud groups.
Syllabus
  • The subject of organic chemistry. Nomenclature of organic chemistry. Name of compounds for-mation. Chemical bonds and bonding in organic molecules. Hybridization of the carbon atom, bon-ding 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 mecha-nism. Activation energy and enthalpy of the reaction. Chemical. Acidity and basicity. Arrhenius, Brøn-sted and Lewis explanation, acids and bases, pKa and pH. Spectral properties of organic com-pounds. Electronic spectra. Infrared spectroscopy, Nuclear magmetic resonance, mass spectroscopy. Alkanes and cycloalkanes. Chain isomerie, conformation analysis of alkanes and cycloalkanes. Fu-sed 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. Enantio-mers, 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 stereo-chemistry 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 reacti-ons - electrocyclic reactions, cycloaddition reactions, the rules of their realization, sigmatropic rear-rangements. 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 com-pounds.The phenomenon of aromaticity and its properties. Nonbenzoid aromates (polycyclic aroma-tes, annulenes, aromatic ions.} Mechanism of aromatic electrophilic substitution. Summary of electro-philic reactions, formation of electrophilic reagents. Effect of substituents on the reactivity and orien-tation. Hammet equation, sigma and rho constants. Ipso substitution. Nucleophilic substitution on the aromatic ring (SN1, SN2, elimination-addition mechanism). Conditions for addition reactions and reacti-ons 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
  • POTÁČEK, Milan. Organická chemie : pro biology. 3., opr. vyd. Brno: Masarykova univerzita, 2002, 208 s. ISBN 8021028505. info
  • MCMURRY, John. Fundamentals of organic chemistry. 4th ed. Pacific Grove: Brooks/Cole publishing company, 1998, xxii, 566,. ISBN 0-534-35245-4. info
  • KOVÁČ, Jaroslav, Štefan KOVÁČ and Ľubor FIŠERA. Organická chémia. 2. vyd. Bratislava: Vydavateľstvo STU, 1995, s. 276-629. ISBN 80-227-0791-0. info
  • POTÁČEK, Milan. Organická chemie : pro biology. 1. vyd. Brno: Vydavatelství Masarykovy univerzity, 1995, 208 s. ISBN 8021011254. info
  • SOLOMONS, T. W. Graham. Organic chemistry. 5th ed. New York: John Wiley & Sons, 1992, 1198 s. ISBN 0471552232. info
  • MACHÁČEK, Vladimír, Josef PANCHARTEK and Oldřich PYTELA. Organická chemie. Vyd. 1. Pardubice: Vysoká škola chemicko-technologická, 1991, s. 277-571. ISBN 80-85113-26-0. info
  • HRNČIAR, Pavol. Organická chémia. 3., preprac. vyd. Bratislava: Slovenské pedagogické nakladateľstvo, 1990, 708 s. ISBN 8008000287. info
  • MACHÁČEK, Vladimír and Josef PANCHARTEK. Organická chemie. 1. vyd. Pardubice: Vysoká škola chemicko-technologická, 1989, 276 s. ISBN 80-85113-08-2. info
  • ORCHIN, Milton. Organická chemie : příruční naučný slovník. Translated by Zdeněk Kafka - František Zemánek. 1. vyd. Praha: Státní nakladatelství technické literatury, 1986, 550 s. URL info
  • ČERVINKA, Otakar, Václav DĚDEK and Miloslav FERLES. Organická chemie. 3., nezměn. vyd. Praha: Státní nakladatelství technické literatury, 1982, 791 s. info
  • BUCHAR, Eugen, Jaroslav DOUBRAVA and Tibor LIPTHAY. Organická chemie : pro pedagogické fakulty. 1. vyd. Praha: Státní pedagogické nakladatelství, 1966, 355 s. info
Teaching methods
lectures
theoretical preparation
Assessment methods
Completion: written test (performance 70 %) and oral examination.
colloquium
Language of instruction
Czech
Further comments (probably available only in Czech)
Study Materials
The course is taught annually.
Information on the extent and intensity of the course: 12 hodin.
The course is also listed under the following terms Autumn 2018, Autumn 2019, autumn 2020, Autumn 2022, Autumn 2023, Autumn 2024.
  • Enrolment Statistics (Autumn 2021, recent)
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