Sep 16, 2019   4:01 a.m. Ľudomila, Ľudmila
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Course syllabus 414O4_4B - Organic Chemistry II (FCFT - SS 2019/2020)


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University: Slovak University of Technology in Bratislava
Faculty: Faculty of Chemical and Food Technology
Course unit code: 414O4_4B
Course unit title: Organic Chemistry II
Mode of delivery, planned learning activities and teaching methods:
lecture3 hours weekly (on-site method)
seminar2 hours weekly (on-site method)

 
Credits allocated: 6
 
Recommended semester/trimester: Chemistry, Medical Chemistry and Chemical Materials - bachelor (compulsory), 4. semester
Level of study: 1.
Prerequisites for registration: none
 
Assesment methods:
test
 
Learning outcomes of the course unit:
Acquirement of basic principles of organic reactions based on the mechanism organic reactions and their role in the nature, food and technology
 
Course contents:
Amines
Amines - physical properties, toxicity, stereochemistry. Synthesis - reduction of nitro compounds, amonolysis of halogen derivatives, reduction of nitriles, amides, azides, reductive amination, Gabriel reaction, Hofmann degradation of amides. Model syntheses. Reactions of amines - basicity, alkylation, Hofmann elimination. Cope elimination. Preparation of amides. Preparation of sulfonamides. SE reactions of anilines, sulphonation of anilines, nitrosation of amines, reactions of diazonium ions, Model syntheses for the preparation of bromo-, chloro-, iodo-, fluoro, hydroxy-derivatives,. Model syntheses. Preparation and reactions of azobenzenes, benzidine rearrangement, naftalen-2-amine.

Carbonyl compounds

Aldehydes and ketones. Structure of carbonyl group - reactivity. Preparation of aldehydes and ketones - oxidation of alcohols (Jones, PCC, MnO2, CrO3, Swern), ozonolysis of alkenes, hydratation of alkynes (Markovnikov vs. Brown). - F. C. acylation. Oxidation of alkyl benzenes, Gattermann-Koch, reduction of alkanoyl halides, DIBAL reduction of esters, reduction of nitriles, reactions of alkanoyl halides with dialkyl cuprates, pyrolysis of carboxylic acids salts.
Reactions of carbonyl compounds and their structure. Hydrogenation.
Ionic additions, additions of hydrides and organometallic reagents. Model synthesis of alcohols from carbonyl compounds. Hydratation. Additions of alcohols.
Acetales as protecting groups, protection of vicinal alcohols, C-vitamine, cyclic thioacetales, umpolung. Nucleophilic addition of ammonia and their derivatives, pyridoxamine and amino acids, enamines, deoxygenation of carbonyl group - Wolf-Kizhner, McMurry.
Cyanohydrin synthesis. Benzoine condensation. Benzil rearrangement. Wittig reaction. Model syntheses of alkenes. Addition of sulphur ylides, Baeyer-Villiger. Cannizzaro, Claisen-Tiščenko.

Enols and enones. Unsaturated carbonyl compounds
Enols and enones - acidity of aldehydes and ketones, ambidentity, keto-enol equilibria, mechanisms. Deuteration, stereoisomerization. Acidic halogenation of ketones. Favorskij rearrangement. Basic halogenation of ketones, halophorm reaction. Alkylation of ketones via enolates and enamines. Aldol condensation, mechanisms. Additions and dehydratation, E1cb elimination, cross aldol condensation, pentaerythritol, Semtex.
Intramolekular aldol condensation. Utilization of aldol condensation in synthesis. Related reactions (Henry, Knoevenagel, Döbner, Perkin).
Unsaturated carbonyl compounds - structure, 1,2- a 1,4-addition, mechanisms- Model additions, 1,2- and 1,4-addition of organometallic reagents, Michael addition, Robinson annulation.

Carboxylic acids

Carboxylic acids - structure, acidity. Effect of substituent. Benzoic acids - acidity. Generation of salts, protonation of carboxylic acids.
Synthesis of carboxylic acids - oxidation of alcohols, carboxylation of organometallic reagents, nitril synthesis. Utilization of malonic ester, Model. Esterification, mechanisms, lactones. Reaction of carboxylic acids with diazomethane.
Preparation of alkanoyl halides and anhydrides. Reaction carboxylic acids with ammonia, amides, imides, lactams. Carboxylic acids - reduction with LAH, Hell-Volhard-Zelinskij - mechanisms, utilization in synthesis. Decarboxylation, Hunsdiecker-Borodin.

Carboxylic acids derivatives

Carboxylic acids derivatives, reactivity, structure, addition-elimination mechanism, catalysis with acid and base, basicity, acidity. Alkanoyl chorides - hydrolysis, alkoholysis, ammonolysis, R2CuLi, LAH, LiAlH(OR)3, Curtius (Sevin, Bhopal), Arndt-Eistert. Anhydrides of carboxylic acids - hydrolysis, alkoholysis, ammonolysis, protection. Aspirin, paracetamol. Esters - hydrolysis, presterification, PVA, ammonolysis, alkylation of esters, reduction of esters, LAH, DIBAL. Amides, reduction, hydrolysis. Nitriles, hydrolysis, preparation of ketones.

Dicarbonyl compounds
Dicarbonyl compounds. Claisen ester condensation, mechanism, Dieckmann. Cross Claisen ester condensation, inter- and intramolar. Dekarboxylation of ketoacids. Dicarbonyl compounds as synthetic intermediates. Michael addition. Robinson annulation.
Dicarboxylic acids - Preparation, acidity, reactions. Utilization of phthalic anhydride for separation of chiral alcohols, Gabriel synthesis. Hydroxy acids, preparation, Reformatskij synthesis. Dehydratation, synthesis of lactones. Stereochemistry of hydroxy acids, synthesis of D- and L- lactic acid. Tartaric acid, configuration and synthesis from glyceraldehyde.

Amino acids

Amino acids. Structure and properties - acidity and basicity, zwitterions, isoelectric point, configuration, chirality. Preparation of amino acids. HVZ - amination, malonic ester synthesis, Gabriel and Strecker synthesis, preparation of enentiomeric pure amino acids. Asymmetric synthesis, PTC.
Peptides, proteins. Geometry of peptide bonds, sequence. sequence analysis, Sanger and Edman degradation Synthesis of peptides, protection, Cbz, Boc. Generation of peptide bonds, DCC, Preparation of Gly.Ala. Merrifield synthesis.

Saccharides

Saccharides - classification, D,L-system. Conformation, anomers, epimers, anomeric effect (HOMO-LUMO interpretation). Mutarotation. Reactions - oxidation, brom/water, HNO3, reduction, sorbitol. Fehling, Tollens, basic isomerisation, epimerization, HIO4, osazones, epimers. Generation of esters, eters, glykosides. Kiliani-Fischer, Ruff. Relative configuration of aldoses, Fischer confirmation of D-glucose. Disaccharides - saccharose, maltose, cellobiose, lactose. Polysaccharides - cellulose.
 
Recommended or required reading:
Basic:
KOVÁČ, Š. -- KOVÁČ, J. -- FIŠERA, L. Organická chémia. Bratislava: vydavateľstvo Alfa, 1992.
VOLLHARDT, P. -- SHORE, N. Organic Chemistry /third edition/. New York: W. F. Freeman and Company, 1999.

 
Language of instruction: slovak or english
 
Notes:
The course is recommended for students in the second year of study in the program Chemistry, medicinal chemistry and materials
 
Courses evaluation:
Assessed students in total: 840

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18,6 %17,4 %23,8 %18,2 %18,3 %3,7 %
Name of lecturer(s): prof. Ing. Ľubor Fišera, DrSc. (person responsible for course) - slovak, english
 
Last modification: 29. 1. 2019
Supervisor: prof. Ing. Ľubor Fišera, DrSc. and programme supervisor


Last modification made by Ing. Tomáš Molnár on 01/29/2019.

Type of output: