SubjectsSubjects(version: 895)
Course, academic year 2021/2022
  
Organic Chemistry II - B110004
Title: Organická chemie II
Guaranteed by: Department of Organic Chemistry (110)
Actual: from 2021 to 2021
Semester: both
Points: 6
E-Credits: 6
Examination process:
Hours per week, examination: 3/2 C+Ex [hours/week]
Capacity: winter:70 / 48 (unknown)
summer:unknown / unknown (unknown)
Min. number of students: unlimited
Language: Czech
Teaching methods: full-time
Level:  
For type: Bachelor's
Additional information: http://předmět je vyučován pouze v zimním semestru
Note: deregister from the exam date if a requisite was not fulfilled
course can be enrolled in outside the study plan
enabled for web enrollment
you can enroll for the course in winter and in summer semester
Guarantor: Budka Jan doc. Ing. Ph.D.
Hodačová Jana doc. Dr. Ing.
Pre-requisite : {x}
Interchangeability : N101006, Z110005
In complex pre-requisite: B110009
This subject contains the following additional online materials
Annotation -
Last update: Kubová Petra Ing. (04.12.2017)
This course is continuation of Organic chemistry I. The course of Organic chemistry II is based on the description of organic reactions according to the mechanistic principles. It also includes chemistry of natural compounds (carbohydrates, amino acids, peptides, nucleic acids) as well as basics of heterocyclic chemistry.
Aim of the course -
Last update: Kubová Petra Ing. (04.12.2017)

Students will be able to:

write mechanisms of reactions in organic chemistry

describe stereochemistry of chemical transformations

estimate reactivity of polyfunctional compounds on the bases of structure

plan two- or three-step synthesis of target compound

know chemical properties of basic building blocks of natural and heterocyclic compounds

Literature -
Last update: Kubová Petra Ing. (04.12.2017)

R: J. McMurry: Organic Chemistry, 8. Edition, Brooks/Cole, Belmont, CA, USA, 2012. 9780840054449

Learning resources -
Last update: Kubová Petra Ing. (04.12.2017)

Electronic workbook: https://och.vscht.cz

Requirements to the exam -
Last update: Budka Jan doc. Ing. Ph.D. (12.09.2021)

1. Organic reactions. Basic classification (addition, substitution, elimination), oxidation and reduction in organic chemistry, oxidation numbers, classification of reagents, the ways of the splitting of chemical bond, reaction mechanism, reaction intermediates, the theory of transition state, reaction coordinate, DG a DG# and their influence on the reaction rate and on the reaction equilibrium.

2. Nucleophilic substitution on saturated carbon atom. Mechanism and stereochemistry and their dependence on the structure of substrate, leaving group and solvent. Competitive reactions. Preparation of alcohols, ethers, thiols, esters, alkylation of ammonia, amines and sulfur derivatives. Gabriel synthesis of amines, preparation of alkylhalides from alcohols using hydrogen halides or halides of inorganic acids, transformation of alcohols to the sulfonates (methanesulfonates and tosylates), sulfonates as the leaving groups, cleavage of ethers, opening of an epoxide ring. Formation of C-C bond by alkylation reactions - preparation of nitriles, reaction of organocooper reagents with alkyl-, alkenyl- and arylhalides.

3. Elimination reactions. E1 and E2 mechanism, relation to the nucleophilic substitution, dehydrohalogenation, Zaitsev's rule, influence of the bulkiness of the base, stereochemistry of the elimination reactions, Hofmann elimination, dehalogenation, dehydration, elimination during the solvolysis (E1), formation of alkynes, nitriles from dehydration of aldoximes, pinacol rearrangement.

4. Hydrocarbon derivatives containing carbonyl group – oxidation levels, redox reactions, reactivity tovards nucleophiles.

Aldehydes and ketones: Nucleophilic addition to unsaturated carbon atom - H – nucleophiles (reduction), O – nucleophiles (hydratation of carbonyl group, acetals, ketals, C – nucleophiles (cyanhydrines and aminonitriles, Grignard reagents, Wittig reaction). N – nucleophiles (addition of ammonia and amines (+ reductive amination), hydrazine and hydroxylamine to aldehydes and ketones). Reaction of oximes – dehydratation of aldoximes, Beckmann rearrangement of ketoximes. Conjugate addition to α,β-unsatzrated carbonyl compounds – addition of HX, alcohols, thiols and amines. Additiob of organometal compounds: Grignard and Gilman reagents.

5. Carboxylic acids and their derivatives - Nucleophilic substitution on the unsaturated carbon atom. Transformation of carboxylic acids derivatives (halides, esters, anhydrides), lactones and lactames. Baeyer-Villiger oxidation. Pyrolysis of acetates. Amides of carboxylic acids – Hofmann degradation, heterocumulenes (isocyanates, ketenes) and addition of nucleophiles. Reaction of carboxylic acids derivatives with organometal compounds and complex hydrides. Hydrolysis of carboxylic acids derivatives and nitriles – synthesis of carboxylic acids, amino- a hydroxyacids. Reaction of amino- a hydroxyacids. Basic derivatives of carbonic acid.

6. Reaction including α-hydrogen: Acidic and basic catalysed enolisation, stability of enoles, consequences of enolisation (Exchange of α-hydrogen with solvent, racemisation of stereogenic centre on α-carbon). Reactions of enoles and enolates with electrophiles (α-halogenation of aldehades and ketones, Lieben reaction, Hell-Volhart-Zelinskij reaction, alkylation of enolates. Michael additio). Acetoacetic and malonate synthesis. Aldol-style reactions (Aldolisation of aldehydes, aldol condensation of ketones, cross-aldol condensation. Claisen and cross-Claisen condensation, condensation of esters with ketones, Dieckmann condensation).

7. Electrophilic addition to unsaturated systems. Addition of hydrogen halides to alkenes and alkynes, hydration of alkenes and alkynes (revision and extension), hydroboration, hydroboration/oxidation, addition of halogens, formation of halohydrines, epoxidation, dihydroxylation and ozonolysis of alkenes. Carbenes and cyclopropanation including Simmons-Smith reaction. Dienes – 1,2- vs. 1,4-electrophilic addition, Diels-Alder cycloaddition.

8. Electrophilic substitution on unsaturated carbon atom. Aromatic electrophilic substitution - introduction of second substituent (mechanism), comparison of benzene, naphthalene, pyrrole, furan, thiophene and pyridine.

9. Nucleophilic substitution on aromatic compounds. Preparation and reactivity of aromatic diazonium salts, their use in organic synthesis. Aromatic nucleophilic substitution (addition-elimination and elimination-addition mechanism).

10. Heterocycles - basic types of five- and six-membered heterocycles, aromaticity. Preparation and reactivity of five-membered heterocycles and of indole. Six-membered heterocycles containing nitrogen - pyridine, quinoline, isoquinoline, principle of their synthesis. Basicity, reactions on nitrogen, electrophilic and nucleophilic substitution reactions.

11. Radical reactions. Formation of radicals, structure and stability of radicals. Radical halogenation of alkanes and its selektivity, Halogenation to allylic and benzyl position. Radical addition of HBr (revision) and RSH to alkenes.

12. Oxidation and reduction (revision and extension). Oxidation - oxidation of side chain on the aromatic ring, alcohols, spliting of 1,2-diols with HIO4, quinones. Oxidation of sulphur compounds and amines, Bayer-Villiger oxidation. Reduction - Birch reduction, reduction of alkynes to alkenes. Reduction of aldehydes, ketones, carboxylic acid and their derivatives (Wolff-Kishner, Clemmensen, reductive dimerization - pinacol reaction, acyloin condensation, reduction using complex hydrides, DIBAH and BH3). Cannizzaro reaction. Reduction of nitrogen and sulphur derivatives (nitro compounds, disulfides, sulfonic acids).

13. Amino acids and peptides. Classification of amino acids, coded amino acids, structural types of coded amino acids, acido-basic equilibrium, isoelectric point, synthesis (Strecker synthesis, alkylation of acetamidomalonate). Chemistry of amino acids - behavior of alpha-amino acids on heating, esters of amino acids, acylation of amino acids. Analysis of peptides - amino acid analysis, sequence analysis (Sanger's reagent, dansylation, Edman degradation). Synthesis of peptides - protective groups (Z, Boc, benzyl and t-butyl ester), formation of peptide bond (DCCI, solid phase synthesis).

14. Carbohydrates. Structure, stereochemistry, configuration, cyclic forms, mutarotation, Kiliani–Fischer synthesis, Wohl degradation, oxidation and formation of lactones, reduction and epimerization of carbohydrates, glycosides. Disaccharides - reducing and non-reducing, polysaccharides (starch, cellulose). Principles of nucleobases, nucleotides, nucleic acids; base pairing.

Syllabus -
Last update: Budka Jan doc. Ing. Ph.D. (12.09.2021)

1. Organic reactions, types, mechanisms, acid-base equilibrium.

2. Nucleophilic substitution on saturated carbon. Mechanism, stereochemistry, applications.

3. Elimination E1 and E2. Mechanism, stereochemistry, application.

4. Nucleophilic addition on unsaturated carbon.

5. Nucleophilic substitution on unsaturated carbon.

6. Chemistry of enoles and enolates.

7. Electrophilic additions on unsaturated systems.

8. Electrophilic substitution on unsaturated systems.

9. Nucleophilic substitution on aromatic compounds.

10. Heterocycles. Basic types of five and six membered heterocycles, synthesis and reactivity.

11. Radical reactions, halogenation, additions of HBr and thiols.

12. Oxidation and reduction.

13. Aminoacids, peptides. Structure, chemical properties, synthesis.

14. Carbohydrates. Structure, stereochemistry, chemical properties.

Registration requirements -
Last update: Kubová Petra Ing. (04.12.2017)

Organic Chemistry I

Course completion requirements - Czech
Last update: Kundrát Ondřej Ing. Ph.D. (16.02.2018)

Předmět je zakončen zkouškou, která se skládá z písemné a ústní části. Student může přistoupit ke zkoušce z Organické chemie II poté, co získal zápočet na cvičeních z Organické chemie II.

Teaching methods
Activity Credits Hours
Účast na přednáškách 1,5 42
Příprava na přednášky, semináře, laboratoře, exkurzi nebo praxi 1,5 42
Příprava na zkoušku a její absolvování 2 56
Účast na seminářích 1 28
6 / 6 168 / 168
 
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