Organic Chemistry I - MC270P108A

• Anglický název: Organic Chemistry I
• Český název: Organická chemie I (v angličtině)
• Zajišťuje: Katedra organické chemie (31-270)
• Fakulta: Přírodovědecká fakulta
• Platnost: od 2024
• Semestr: zimní
• E-Kredity: 5
• Způsob provedení zkoušky: zimní s.:písemná
• Rozsah, examinace: zimní 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.
• Vyučující: Dr. Lukáš Rýček, M.Sc.; Mykyta Ziabko
• Neslučitelnost : MC270P61A, MC270P76, MC270P80, MC280P66B
• Ve slož. prerekvizitě: MC270C92, MC270C93

Anotace

The aim of the course is to provide students with the basic knowledge of organic chemistry. Basic principles as well
as reactivity of selected organic compounds (including alkanes, alkenes, alkynes, aromatic compounds, alcohols,
phenols, ethers, thiols, and sulfides) will be discussed.

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

Literatura

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

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

1. Bond theory hybridization, molecular orbital theory, resonance, Broensted and Lewis acid-base theory

2. Alkanes (physical and chemical properties, abundance, stereochemistry, cycloalkanes conformation)

3. Types of organic reactions (ionic and radical reaction), equilibrium (Gibbs energy etc.), bond dissociation energy, energetic diagrams), kinetics (activation energy)

4. Alkenes (physical and chemical properties, stereochemistry, stability, reactions of alkenes (addition reactions of hydrogen halides, halogens, hydratation, hydroboration, carbene addition - Simmons-Smith rxn, hydrogenation, hydroxylation, alkene cleavage, radical reactions, chain reactions. Alkynes, physical and chemical properties, preparation, reactions of alkynes - addition, reduction, cleavage, acido-basic reactions, alkylation of alkynes)

5. Stereochemistry, chirality, symmetry elements, optical activity, R-S nomenclature, enantiomers, diastereomers, meso form.

6. Halogenoalkanes (physical and chemical properties, preparation, Hammond postulate, allylic halogenation, reactions of halogenoalkanes (Grignard and similar organometallic compounds). Oxidation a reduction in organic chemistry. Nucleophilic substitution (SN1 a SN2 mechanism, steric effect, nucleophilicity, effect of solvents, etc.). Eliminations (mechanism E1 and E2).

7. Dienes (physical and chemical properties, preparation, stability, electrophilic addition, kinetically and thermodynamically driven rxns, Diels-alder reaction, conjugation and colors - principle of a vision. Benzene and other aromatic compounds, structure and stability, orbital model, aromaticity, aromatic ions, aromatic heterocycles.

8. Chemistry of the aromatic compounds (electrophilic aromatic substitution - halogenation, nitration, sulfonation, Fridel-Crafts reaction - alkylation, acylation), substitution effects (inductive a mesomeric effect), nucleophilic aromatic substitution, benzyne, reaction on side chain of aromatic compounds (halogenation, hydrogenation, oxidation, etc.), selective synthesis of trisubstituted aromatic compounds.

9. Alcohols and phenols (physical properties, acidity and basicity, preparation of alcohols (reduction oc carbonyl compounds, hydratation a oxidation alkenes, use of organometallic compounds, etc.), reactions of alcohols (dehydratation, substitution, etc.), oxidation of alcohols (Swern, Jones, Dess-Martin oxidation), protection of alcohols. Phenols and their reactions (substitution, oxidation, etc.).

10. Ethers, thiols, sulfides (physical and chemical properties. Structure of ethers, preparation (addition of alcohols on alkenes, Williamson synthesis, alkoxymercuration of alkenes), reaction of ethers (cleavage, Claisen rearrangement). Cyclic ethers, epoxides preparation and reactions (acidic and basic opening), crown-ethers. Thiols, sulfides, preparation and reactions.

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

Výsledky učení

• Understand the fundamental principles of electron theory of bonding, including ionic and covalent bonds, hybridization, and molecular orbital theory.
• Apply the concepts of resonance and both Brønsted and Lewis theories of acids and bases, including pKa values.
• Analyze the knowledge of the physical and chemical properties of alkanes, including their stereochemistry and the conformations of cycloalkanes.
• Analyze various types of organic reactions such as addition, substitution, elimination, and rearrangements, and differentiate between ionic and radical mechanisms.
• Evaluate the Gibbs free energy and dissociation energy in the context of chemical equilibrium and reaction energetics using energy diagrams.
• Understand the stereochemistry and stability of alkenes and their mechanisms of electrophilic addition, including hydration, halogenation, and hydrogenation.
• Apply the principles of alkene reactions to complex processes such as Simmons-Smith reaction, hydroboration, and radical polymerization.
• Understand the preparation and reactions of alkynes, including their acidity, alkylation, and reduction mechanisms.
• Understand the concepts of chirality, including R,S notation, enantiomers, diastereomers, and optical activity in chiral molecules.
• Apply stereochemical principles to molecules without centers of chirality (e.g., allenes and biaryls) and understand the concept of prochirality.
• Evaluate the physical and chemical properties of halogenalkanes and their mechanisms in nucleophilic substitution (SN1, SN2) and elimination reactions (E1, E2).
• Understand the importance of Hammond’s postulate and allylic halogenation in organic reaction mechanisms.
• Analyze the properties and reactions of dienes, including their stability and application in the Diels-Alder reaction.
• Understand the principles of conjugation, color, and the chemical basis of vision in the context of aromatic compounds.
• Evaluate the structure, stability, and aromaticity of benzene and other aromatic heterocycles, using an orbital model.
• Apply knowledge of electrophilic aromatic substitution (e.g., nitration, halogenation, Friedel-Crafts reactions) and predict substituent effects on reactivity and orientation.
• Understand the nucleophilic aromatic substitution and the formation of benzyn intermediates in complex organic reactions.
• Understand the physical and chemical properties of alcohols and phenols, including their acidity and basicity, and apply methods for their preparation and oxidation.
• Evaluate the reactivity of ethers, epoxides, thiols, and sulfides, including their preparation and role in addition reactions and substitutions.
• Create advanced synthetic routes using knowledge of various organic reaction mechanisms, including protection of alcohols, epoxide opening, and Claisen rearrangements.

Poslední úprava: Rýček Lukáš, Dr., M.Sc. (24.09.2024)