CH2RC_2P1P Organic Chemistry

Faculty of Education
Spring 2014
Extent and Intensity
0/0/0. 5 credit(s). Type of Completion: zk (examination).
Teacher(s)
Mgr. Jiří Šibor, Ph.D. (lecturer)
Guaranteed by
doc. RNDr. Petr Sládek, CSc.
Department of Physics, Chemistry and Vocational Education – Faculty of Education
Contact Person: Mgr. Bc. Lucie Viková
Supplier department: Department of Physics, Chemistry and Vocational Education – Faculty of Education
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
At the end of this course, student should be able to:
understand and be able to explains structure and reactivity basic relationships of hydrocarbons;
use data to organic chemistry problem solutions independently;
make reasoned decisions about HC reactivity;
formulate a reasoned differential diagnosis for products deduction of similar reactions;
interpret HC characteristics.
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
  • MCMURRY, John. Fundamentals of organic chemistry. 4th ed. Pacific Grove: Brooks/cole, 1998, xxii, 566. ISBN 0534363547. 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
  • 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
  • BUCHAR, Eugen, Jaroslav DOUBRAVA and Tibor LIPTHAY. Organická chemie : pro pedagogické fakulty. Vyd. 2., upr. Praha: Státní pedagogické nakladatelství, 1973, 370 s. info
  • ČERVINKA, Otakar, Václav DĚDEK and Miloslav FERLES. Organická chemie. Vyd. 1. Praha: SNTL - Nakladatelství technické literatury, 1969, 1070 s. info
Teaching methods
lectures
theoretical preparation
Assessment methods
Completion: written test (performance 70 %) and oral examination.
Language of instruction
Czech
Further comments (probably available only in Czech)
Information on the extent and intensity of the course: 12 hodin.
The course is also listed under the following terms Spring 2006, Spring 2007, Spring 2008, Spring 2009, Spring 2010, Spring 2011, Spring 2012, Spring 2013, Spring 2015, Spring 2016, Spring 2017, Spring 2018.
  • Enrolment Statistics (Spring 2014, recent)
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