C3050 Organic Chemistry II

Faculty of Science
Autumn 2013
Extent and Intensity
4/0/0. 4 credit(s) (plus extra credits for completion). Type of Completion: zk (examination).
Teacher(s)
prof. RNDr. Milan Potáček, CSc. (lecturer)
RNDr. Slávka Janků, Ph.D. (seminar tutor)
Mgr. Jaromír Literák, Ph.D. (seminar tutor)
Mgr. Jakub Švenda, PhD. (seminar tutor)
Guaranteed by
prof. RNDr. Milan Potáček, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science
Timetable
Wed 8:00–9:50 B11/132, Fri 8:00–9:50 B11/132
Prerequisites
C2021 Organic Chemistry I
Knowledge of General Chemistry and Organic Chemistry I
Course Enrolment Limitations
The course is also offered to the students of the fields other than those the course is directly associated with.
fields of study / plans the course is directly associated with
Course objectives
During the course the students are acquainted with chemistry of hydrocarbons derivatives, their structure assessment and reactivity of different functional groups, their influence upon the hydrocarbon skeleton and the opposite influence of these different skeletons upon the functional group. In an overview students are informed about such complex molecules like saccharides, steroids and heterocyclic compounds. The main aim of the course is understand the structure of the single functional groups and their behaviour in dependence upon character of the hydrocarbon skeleton with the target to evaluate the chemical properties of complex molecules.
Syllabus
  • Organic Chemistry II Organic Chemistry of Hydrocarbons Derivatives Overview of various structures of organic molecules and their reactivity based on described structures including simple heterocyclic compounds. Basic mechanism of the main types of reactions. Methods of preparation of the main classes of derivatives is given. 1. Halogen derivatives. Influence of the carbon skeleton on the reactivity of halogen derivative. Mechanism of nucleophilic substitution, SN1, SN2; mechanisms and their sterochemical course. 2. Elimination reactions, mechanisms E1, E2, E1cB and their stereochemical course. Substitution versus elimination. Alpha elimination reactions. 3. 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 part of the alcohol molecule. Oxidation reactions. Polyhydroxy derivatives. 4. 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. 5. 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. 6.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. 7. 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). 8. 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. 9. Organometallic compounds. Nomenclature. Relation between the metal and the chemical properties. Representatives of organometallic compounds, their reactivity and application in organic synthesis. Preparation. 10. 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. 11. 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. Disaccharides (their structure and reductive properties). Polysaccharides - homo and heteropolysaccharides, representatives. Cellulose, its preparation and modification, application. Starch. 12. 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). 13.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. 14.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).
Literature
    recommended literature
  • MCMURRY, John. Organická chemie. Translated by Jaroslav Jonas. Vyd. 1. Praha: Vysoká škola chemicko-technologická v Praze, 2007, 1 sv. ISBN 9788070806371. info
  • CLAYDEN, Jonathan. Organic chemistry. 2nd ed. Oxford: Oxford University Press, 2012, xxv, 1234. ISBN 9780199270293. info
  • LITERÁK, Jaromír. Sbírka řešených příkladů k semináři z organické chemie (Collection of Excercises in Organic Chemistry). 1. vydání. Brno: Masarykova univerzita, 2012, 308 pp. ISBN 978-80-210-5810-1. info
    not specified
  • MCMURRY, John. Organic chemistry. 6th ed. Pacific Grove: Brooks/Cole publishing company, 2004, 1243 s. +. ISBN 0-534-38999-62-7.
  • SOLOMONS, T. W. Graham. Organic chemistry. 6th ed. New York: John Wiley & Sons, 1996, xxvii, 121. ISBN 0471013420. info
  • ČERVINKA, Otakar. Chemie organických sloučenin. 1. vyd. Praha: Státní nakladatelství technické literatury, 1985, 1131 s. info
  • ČERVINKA, Otakar. Chemie organických sloučenin. Vyd. 1. Praha: Státní nakladatelství technické literatury, 1987, 1052 s. info
  • POTÁČEK, Milan, Ctibor MAZAL and Slávka JANKŮ. Řešené příklady z organické chemie (Problems and Solutions in Organic Chemistry). 2nd ed. Brno: Masarykova univerzita, 2008, 243 pp. ISBN 80-210-2274-4. info
  • NOVÁČEK, Eduard and Milan POTÁČEK. Laboratorní technika ke cvičení z metod organické chemie. Edited by Slávka Janků. 1. vyd. Brno: Masarykova univerzita, 1997, 91 s. ISBN 8021015004. info
Teaching methods
lectures with a demontration of the taught topic on chosen examples
Assessment methods
The course is represented by a set of lectures and seminars where various phenomena are demonstrated on chosen examples. During the semestr 3 written tests always from part of the lecture contents are organized. The final examination consists from written test and oral examination. Minimum 60% is required for entrance to oral examination.
Language of instruction
Czech
Follow-Up Courses
Further comments (probably available only in Czech)
Study Materials
The course can also be completed outside the examination period.
The course is taught annually.
Listed among pre-requisites of other courses
The course is also listed under the following terms Autumn 1999, Autumn 2000, Autumn 2001, Autumn 2002, Autumn 2011 - acreditation, Autumn 2012, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.
  • Enrolment Statistics (Autumn 2013, recent)
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