C2700 Basic Organic Chemistry

Faculty of Science
spring 2018
Extent and Intensity
2/0/0. 2 credit(s) (fasci plus compl plus > 4). Type of Completion: zk (examination).
Teacher(s)
doc. RNDr. Pavel Pazdera, CSc. (lecturer)
Supervisor
doc. RNDr. Pavel Pazdera, CSc.
Department of Chemistry - Chemistry Section - Faculty of Science
Supplier department: Department of Chemistry - Chemistry Section - Faculty of Science
Prerequisites
( C1601 General and Inorg. Chemistry || C1020 General Chemistry || C1021 General Chemistry ) && ! C2021 Organic Chemistry I && ! C3022 Organic Chemistry II/1 && ! C3050 Organic Chemistry II && ! NOWANY ( C2021 Organic Chemistry I , C3022 Organic Chemistry II/1 , C3050 Organic Chemistry II )
Knowledge of the generall chemistry and inorganic chemistry.
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 the course is directly associated with
Course objectives
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.
Syllabus
  • 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.
Literature
    required literature
  •  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
    recommended literature
  •  Doporučené názvoslovné principy IUPAC (angl..): http://www.acdlabs.com/iupac/nomenclature/; (české): http://www.imc.cas.cz/cz/umch/iupaccentre.htm.
  •  SVOBODA, J., Organická chemie. 1. vydání. Praha: VŠCHT, 2005. http://vydavatelstvi.vscht.cz/knihy/uid_isbn-80-7080-561-7/pages-img/obsah.html.
  •  Jmenné reakce: http://www.organic-chemistry.org/namedreactions/; http://www.chempensoftware.com/organicreactions.htm.
  •  E-knihy na http://books.google.com/: klíčová slova pro vyhledávání: Organic Chemistry; Stereochemistry; Chemical nomenclature; apod.
  •  http://en.wikipedia.org/wiki/Main_Page.
  •  http://cs.wikipedia.org/wiki/Hlavn%C3%AD_strana.
  • POTÁČEK, Milan, Ctibor MAZAL and Slávka JANKŮ. Řešené příklady z organické chemie. 1. vyd. Brno: Masarykova univerzita v Brně, 2000. 243 pp. ISBN 80-210-2274-4. info
  • SOLOMONS, T. W. Graham. Organic chemistry. 6th ed. New York: John Wiley & Sons, 1996. xxvii, 121. ISBN 0471013420. info
  • MCMURRY, John. Organic chemistry. 4th ed. Pacific Grove: Brooks/Cole publishing company, 1995. 1243 s. +. ISBN 0-534-23832-7. info
  • MARCH, Jerry. Advanced organic chemistry : reactions, mechanisms and structure. 4th ed. New York: John Wiley & Sons, 1992. xv, 1495. ISBN 0471601802. info
  • CAREY, Francis A. and Richard J. SUNDBERG. Advanced Organic Chemistry, Part B. New York: Plenum Press, 1990. 800 pp. info
  • HRNČIAR, Pavol. Organická chémia. 3., preprac. vyd. Bratislava: Slovenské pedagogické nakladateľstvo, 1990. 708 s. ISBN 8008000287. info
  • MORRISON, Robert Thornton and Robert Neilson BOYD. Organic chemistry [Morrison, 1987]. 5th ed. Boston: Allyn and Bacon, 1987. 1413 s. ISBN 0-205-08453-2. info
  • ROBERTS, John D. and Marjorie C. CASERIO. Modern organic chemistry. New York: W.A. Benjamin, 1967. 844 s. info
  • CRAM, Donald J. Organic chemistry [Cram, 1964]. Edited by George S. Hammond. 2nd ed. New York: McGraw-Hill Book Company, 1964. 846 s. info
Teaching methods
Lectures.
Assessment methods
One written final test with ten questions(51% of correct answers is needed to pass) + the oral exam.
Language of instruction
Czech
Further Comments
The course can also be completed outside the examination period.
The course is taught annually.
The course is taught: every week.
Listed among pre-requisites of other courses
The course is also listed under the following terms Spring 2008 - for the purpose of the accreditation, Spring 2011 - only for the accreditation, Spring 2001, Spring 2002, Spring 2003, Spring 2004, Spring 2005, Spring 2006, Spring 2007, Spring 2008, Spring 2009, Spring 2010, Spring 2011, Spring 2012, spring 2012 - acreditation, Spring 2013, Spring 2014, Spring 2015, Spring 2016, Spring 2017.
  • Enrolment Statistics (recent)
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