Organic chemistry 0600-S1-O-CORGa

The essence of organic chemistry. The importance of carbon compounds to hymans. The genesis of coal. Allotropic variety of carbon. Fullerenes, Carbon nanotubes. Coal as fuel.
Alkanes: Alkanes as a class of hydrocarbons. Laboratory and industial methods for the synthesis of alkanes. Bergius and Fischer-Tropsch processes. Oil. Natural gas. Refining of crude oil. The octane and cetane numbers of fuels. Nomenclature of alkanes. Conformations of alkanes. Combustion of alkanes. Free radical bromination and chlorination of alkanes.
Cycloalkanes: Cycloalkanes nomenclature. Cyclopropane structure. The stability of cycloalkanes. Bayer tensions theory. Conformations of derivatives. Disintegration of carbon-carbon covalent bond. Carbocation and free radical.
Alkenes: Structure of ethene. Alkenes nomenclature. Laboratory methods for the preparation of alkenes. Dehydration of alcohols as a method for the synthesis of alkenes. E1 and E2 elimination reactions. Dehydrohalogenation of alkyl halides. Debromination of vicinal dibromides. Addition reactions to elefins. Mechanism of electrophilic addition to alkenes. Hydrogenation of alkenes. Addition of electrophilic addition to alkenes. Hydrogenation of alkenes. Addition reaction of metal hydroxide to form alkenes. Markovnikov's rule and the exceptions to this rule. Addition of sulfuric acid. Bromination reaction. Bromonium ion. Halohydrines. Addition of water to olefins. The epoxidation of olefins and acidic hydrolysis. Dimerization of alkenes. Oxidative degradation of alkenes. Ozonolysis. The oxidation of alkenes using KMnO4 and OsO4. Oxymercuratiob-demercuration of alkenes. Hydroboration-oxidation of alkenes. Isomerization of boroorganic compounds.
Dienes: Types of dienes. Methods for the synthesis of dienes. Chemical properties of conjugated dienes. Resonance of conjugated dienes. 1,2-Addition and 1,4-addition of conjugated dienes. Allyl cation and its construction. The Diels-Alder reaction. Stereochemical aspects of the Diels-Alder reaction.
Alkynes: Nomenclature. Physical and chemical properties. Syn- and anti addition of hydrogen to alkynes. The acidity of acetylene and terminal alkynes. Silver and copper acetylides. Synthesis of alkynes bythe elimination of the vicinal dibromides. Synthesis of alkynes from ketones. Addition of halogens to alkynes. Addition of hydrogen halogides to alkynes. Addition of water to alkynes. Rautomerism. The oxidative disintegration of alkynes.
Nucleophilic substitution: SN1 and SN2 mechanisms. Influence of various factors on the reactions. Energy profiles and the transition state structures for nucleophilic substitution. Competition between nucleophilic substitution reactions and elimination.
Isomerism: Optical isomerism. Stereochemistry of organic compounds. Specific rotation. Concepts: enantiomer, racemate, diastereomer, meso compound. Fischer projection. Substituents priority rules.
Aromatic compounds: Structure of benzene. Reactions of benzene and differences with other hydrocarbons. Stability of benzene. Aromacity. The Hueckel rule. Molecular orbital description of benzene. Annulenes. Aromatic ions. Polycyclic aromatic compounds. Heterocyclic aromatic compounds. The mechanism of aromatic electrophilic substitution. Aromatic bromination and chlorination. Nitration and sulfonation of aromatic rings. The Friedel-Crfts alkylation and acylation reactions. Recctivity of aromatic rings. Alkyl derivatives of benzene and their reactions. Halogenation of alkylbenzene side chains. Alkenyl benzene derivatives and their addition reactions. Benzyl radical and cation. Organometallic compounds. Organic compounds of lithium, magnezium, boron, zinc, mercury, and coopper - synthesis, structure, properties and applications. Alcohols, phenols, ethers, crown ethers. Aldehydes and ketones, enols and enolate ions, aldol reactions. Carboxylic acids. acyl chlorides and anhydrides. Esters, esterification, Claisen condensation of esters, syn-elimination. Amides, sulfonamides, chemotheraty - historical aspects. Amines, quaternary ammonium salts and hydroxides. Hofmann elimination, phase transfer catalysis, enamine. Dicarbonyl compounds, acetoacetic and malonic esters. Reactive intermediates - carbocation, carboanion, free radical, carbene, nitrene, benzyne.
Macromolecules: The main methods of synthesis of macromolecules. The polymerization and polycondensation.The most important class of polymers.
Natural compounds and biopplymers: Carbohydrates - classification, monosaccharides - chain and cyclic forms, mutarotation, reactions: building and reconstruction, disaccharides, polysaccharides. Amino acids - structure, acid-base properties, isoelectric point, and synthesis reactions. Polypeptides - structure determination. Synthesis of polypeptides.
Laboratory:
Techniques of laboratory work and determination of physical constants: crystallization, distillation (simple, fractional and steam distillation), extraction and sublimation. Thin layer chromatography (TLC), gas chromatography (GC) and infrared analysis IIR). Realization of 8 preparations in the field of the substitution reaction, Diels-Alder addition, elimination (dehydration), oxidation, reduction, electrophilic substitution on the aromatic ring, esterification and condensation. Complete three tasks in the field of qualitative analysis of organic compounds.
Tutorial:
These classes are dedicated to solving of simple problems with the basics of organic chemistry discussed in the lecture, nomenclature of organic compounds and the reaction mechanisms occurring in this class of compounds. Nucleophilic substitution and elimination reactions, addition to the double bond, electrophilic substitution on the aromatic ring and the aldol condensation will be discussed.

Total student workload

Contact hours with teacher: - participation in lectures - 75 hrs - participation in the laboratory - 105 hrs - participation in the tutorial - 30 hrs - consultation with an academic teacher - 10 hrs Self-study hours: - preparation for laboratory - 55 hrs - preparation for the test - 40 hrs - preparation for the exam - 60 hrs Total number of hours 375h / 15 ECTS points

Learning outcomes - knowledge

Student W1: knows the nomenclature of organic compounds at an advanced level. W2: has knowledge of the functional groups of organic compounds, their transformation, and reaction mechanisms. W3: knows the role of the experiment in transforming functional groups.

Learning outcomes - skills

Student U1: can use chemical nomenclature in the field of organic chemistry. U2: recognizes the functional groups of organic compounds and knows their transformation methods. U3: conducts experiments in the field of organic chemistry

Learning outcomes - social competencies

Student K1: works independently and effectively with a large amount of information and correctly draws conclusions from the experiments performed. K2: conscientiously, accurately, and systematically performs the assigned tasks; K3: aims to develop and acquire new knowledge, skills, and experiences; sees the need to constantly improve professional competencies. K4: has a positive attitude to difficulties standing in the way of achieving the assumed goal and meets the deadlines.

Teaching methods

Lecture: Conventional lecture with the use of multimedia presentation. Laboratory: Syntheses of preparations and analyzes of the obtained compounds completed with the preparation of reports. Auditorium exercises consist in solving problems in the field of organic chemistry with the use of elements of the lecture, discussion, and talk.

Expository teaching methods

- problem-based lecture
- informative (conventional) lecture
- discussion

Exploratory teaching methods

- seminar
- laboratory

Type of course

compulsory course

Prerequisites

Basic knowledge of general chemistry, analytical chemistry and instrumental methods.

Course coordinators

Jacek Ścianowski

Learning outcomes

After a lecture a student can recognize basic functional groups present in organic compounds and to show an influence on kinds of their transformations. He explains mechanisms of organic compounds on the basis of electron effects and presents the most important industrial synthesis of organic compounds. After ending of excercises a student can name basic organic compounds according to the obligatory nomenclature. He can also to interpret the addition directions to alkenes and alkynes depending on reaction conditions. A student recognized an absolute configuration of optically active compouds and can count of enantiomeric excess. He can explain differences of velocity rates of nucleophilic substitutions depending on an order of carbon atoms and designates directions and facility of electrophilic substitution in substituted aromatic compounds. A student can also planed several step syntheses of organic compounds using typical chemical reactions.

Assessment criteria

Assessment methods:
Lecture: written examination. W1,W2, U1, U2,U3, K1, K2, K3, K4.
Laboratory: credit on the basis of laboratory exercises and elaborations. Nine written tests per semester - W1, W2, W3, U1, U2, U3 continuous evaluation of the student in the laboratory - K1, K2, K3, K4.
Tutorial: credit on the basis of two written tests per semester - W1, W2, W3, U1, U2, continuous evaluation of the student in the classroom - K1, K2, K3, K4.

Assessment criteria:
fail - 50% <
satisfactory - 50-60%
satisfactory plus - 61-65%
good - 66-75%
good plus - 76-80%
very good - 81% >

Practical placement

not applicable

Bibliography

Basic literature:
1. T.W.G. Solomons, C.B. Fryhle, Organic Chemistry, 7th Ed., J. Wiley, New York, 2000.
2. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001.
3. B.S. Furniss, A.J. Hannaford, P. W. G. Smith, A. R. Tatchell, Vogel's Textbook of Practical Organic Chemistry, 5th Edition, LongmanScientific&Technical, Essex 1989.
4. Vogel's Textbook of Practical Organic Chemistry, 5th Edition, LongmanScientific&Technical, Essex 1989.
5. R.L. Shrirer, Ch. K. F. Hermann, T. C. Morrill, D. Y. Curtis, R. C. Fuson, The Systematic identification of Organic Compounds, 7th dition, J. Wiley, New Yor, 1998.
Additional lecture:
1. J. McMurry, Chemia organiczna, PWN, Warszawa 2001.
2. R.T. Morrison, R. N. Boyd, Chemia Organiczna, PWN, Warszawa, 1990
3. P. Tomasis, Mechanizmy reakcji organicznych, PWN, Warszawa 1998
4. Laboratorium chemii organicznej, praca zbiorowa pod redakcją Piotra Kowalskiego, WNT, Warszawa, 2004.

Additional information

Additional information (registration calendar, class conductors, localization and schedules of classes), might be available in the USOSweb system:

Description of 0600-S1-O-CORGa in USOSweb