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Předmět, akademický rok 2024/2025
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Organic Chemistry II - MC270P108B
Anglický název: Organic Chemistry II
Český název: Organická chemie II (v angličtině)
Zajišťuje: Katedra organické chemie (31-270)
Fakulta: Přírodovědecká fakulta
Platnost: od 2024
Semestr: letní
E-Kredity: 5
Způsob provedení zkoušky: letní s.:písemná
Rozsah, examinace: letní s.:3/2, Z+Zk [HT]
Počet míst: neomezen
Minimální obsazenost: neomezen
4EU+: ne
Virtuální mobilita / počet míst pro virtuální mobilitu: ne
Stav předmětu: vyučován
Jazyk výuky: angličtina
Poznámka: povolen pro zápis po webu
Garant: Dr. Lukáš Rýček, M.Sc.
Neslučitelnost : MC270P61A, MC270P76, MC270P80
Anotace - angličtina
The aim of the course is to provide students with the basic knowledge of organic chemistry. Basic reactivity of
selected organic compounds (including carbonyl compounds such as aldehydes ketones, carboxylic acid and
derivatives, amines, aminoacids, and sugars), will be discussed as well as pericyclic reactions.
Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (17.02.2022)
Literatura - angličtina

1. J. McMurry - Organic Chemistry, 8th ed., Brooks/Cole, 2012

2. S. McMurry - Organic Chemistry Study Guide and Solution Manual, 8th ed., Brooks/Cole, 2011

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (23.05.2022)
Požadavky ke zkoušce - angličtina

The credits from the tutorial course are needed for enrolling for the exam.

The exam will be in the written form, covering the material discussed during the lectures and included in the recommended literature.

The conditions for successful fulfilling of the tutorial lectures are as follows:

  • 70% attendance (in case of absence higher then 30%, it is necessary to rationalize the absence by a medical or other document)
  • Working out four homeworks.
  • Passing a final test with at least 60%.

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (17.02.2022)
Sylabus - angličtina

1. Aldehydes and ketones: preparation, reactivity oxidation of aldehydes, relative reactivity. Nucleophilic addition to aldehydes and ketones: hydration, addition of HCN, addition of organometallic species, addition of amines and hydrazines.

2. Other reactions involving attack of the carbonyl carbon: reduction of karbonyl to alkanes (Wolff-Kischner reaction, Clemmenson reduction), conversion of carbonyl compounds to alkenes (Wittig olefination, Peterson olefination, Tebbe reaction).

3. Carboxylic acids and nitriles. Physical properties of carboxylic acids. The influence of the structure on the acidity of carboxylic acids. Preparation of the carboxylic acids (, benzylic oxidation, oxidative cleavage of alkenes, oxidation of alcohols and aldehydes, hydrolysis of nitriles, carboxylation of Grignard reagents, haloform reaction, Kolbe-Schmitt reaction, Arndt-Eistert reaction, Favorski rearrangement. Reactions of carboxylic acids: reduction. Preparation of nitriles by dehydration of amides. Reaction of nitriles: addition of water, organometallic reagents, reduction.

4. Carboxylic acid derivatives. Nucleophilic acyl substitution. Relative reactivity of carboxylic derivatives. Preparation of acyl halides, esters and amides from carboxylic acids. Reaction of acyl halides, Chemistry of acid anhydrides, chemistry of esters and amides

5. Keto-enol tautomerism (acid and base catalyzed). Enol reactivity and mechanism of alpha-substitution. Alpha-halogenation of aldehyde and ketons (Favorski rearrangement), of carboxylic acids (Hell-Volhard-Zielinski). Acidity of alpha hydrogens in carbonyl compounds, enolates and their reactivity: halogenation, haloform reaction, alkylation (malonester, acetoacetate syntheses). Kinetic and thermodynamic alkylation of enolates.

6. Condenstaion of carbonyl compounds. Condensation of aldehydes and ketones, enolization enone formation, mixed aldol reactions, Mukaiyama aldol reaction. Intramolecular aldol condemsation. Claissen condensation, mixed Claissen condensation, Diecmann condensation, Sobbe condensation, Knoevenagel condensation, Michael addition, Robinson annelation, Wieland-Miescher and Hajos-Parrish Ketones. Stork reaction.

7. Amines and their bondin arrangments. Physical properties of amines. Basicity of various amines. Preparatiopn of amines (nitrile reduction, , reduction of nitro compounds, substitution reactions, Sandmayer reaction, synthesis via azides, Gabriel synthesis, erductive amination, Delephin reaction). Hofmann and Curtius rearrangement, Hofmann elimination, Electrophylic aromatic substitution of aryamines, Diazonium salts.

8. Saccharides. Classification of sacharides, cyclic and linear structure of sacharides. Anomers and mutarotation. Reactions of monosaccharides: esterification, formation of ethers. , Williams reaction, Koenigs-Knorr reaction and its mechanism. Reductions and oxidations of sugars. Chain elongation and shortening (Kiliani-Fisher reaction and Wohl reaction). Disacharides, polysaccharides, deoxysacharides, aminosacharides, ascorbic acid.

9. Aminoacids, peptides and proteins. Structure of aminoacids, Fisher projection, Isoelectric point, Aminoacid synthesis, peptides and proteins. Peptide covalent bond. Structure of peptides and its determination (Edman degradation). Synthesis of peptides (Merryfield synthesis). Structure of proteins.

10. Biomolecules and lipids. Soups, prostaglandins, terpenoids, steroids and their structure. Heterocyclic compounds. Five and six-membered heterocycles and their reactions. Nucelosides, nucleotides and nucleic acids.

11. Pericyclic reactions. Classification of pericyclic reactions (electrocyclic, cycloadditions, sigmatropic rearrangement). Molecular orbitals. Frontier orbitals. Stereochemistry of electrocyclic reactions under thermal and light driven reactions. Cycloadditions: Diels-Alder reaction, [2+2]-cycloadditions. Sigmatropic rearrangement, clasification and examples (Claisen rearrangement, Cope rearrangement).

Poslední úprava: Matoušová Eliška, PharmDr., Ph.D. (17.02.2022)
Výsledky učení - angličtina
  • Understand the preparation and reactivity of aldehydes and ketones, including nucleophilic addition reactions (e.g., hydration, HCN addition, organometallic addition).
  • Understand the carbonyl reactivity such as the reduction to alkanes (Wolff-Kishner, Clemmensen) and the conversion of carbonyls to alkenes via Wittig, Peterson, and Tebbe reactions.
  • Analyze the physical and chemical properties of carboxylic acids and nitriles, and understand how structure influences acidity. Prepare carboxylic acids and nitriles through various oxidation reactions and hydrolysis mechanisms.
  • Apply the mechanisms of nucleophilic acyl substitution to understand the reactivity of carboxylic acid derivatives (acyl halides, esters, amides) and their chemical transformations.
  • Analyze the process of keto-enol tautomerism and alpha-substitution in carbonyl compounds, including the acidity of alpha-hydrogens and enolate reactivity (e.g., halogenation, alkylation).
  • Understand condensation reactions of aldehydes and ketones, and apply them in complex mechanisms like aldol reactions, Claisen condensation, Michael addition, and Robinson annulation.
  • Evaluate the basicity of amines and their physical properties, while applying methods for amine preparation (e.g., nitrile reduction, Gabriel synthesis, reductive amination) and reactions involving aromatic amines.
  • Understand the classification and structure of saccharides, including cyclic and linear forms, mutarotation, and anomers, and analyze their reactions (esterification, reduction, oxidation) and mechanisms like the Koenigs-Knorr reaction.
  • Analyze the structure and synthesis of amino acids, peptides, and proteins, including Fischer projection, isoelectric points, and methods like Edman degradation and Merrifield peptide synthesis.
  • Understand the structure and roles of biomolecules such as lipids, terpenoids, steroids, and prostaglandins, as well as heterocyclic compounds like five- and six-membered rings.
  • Evaluate pericyclic reactions, their classification (electrocyclic, cycloadditions, sigmatropic rearrangements), and apply molecular orbital theory to understand reaction stereochemistry in processes like Diels-Alder and [2+2] cycloadditions.
Poslední úprava: Rýček Lukáš, Dr., M.Sc. (24.09.2024)
 
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