Organic Chemistry I - MC270P108A

• Title: Organic Chemistry I
• Czech title: Organická chemie I (v angličtině)
• Guaranteed by: Department of Organic Chemistry (31-270)
• Faculty: Faculty of Science
• Actual: from 2023
• Semester: winter
• E-Credits: 5
• Examination process: winter s.:
• Hours per week, examination: winter s.:3/2, C+Ex [HT]
• Capacity: unlimited
• Min. number of students: unlimited
• 4EU+: no
• Virtual mobility / capacity: no
• State of the course: taught
• Language: English
• Note: enabled for web enrollment
• Guarantor: Dr. Lukáš Rýček, M.Sc.
• Teacher(s): Dr. Lukáš Rýček, M.Sc.; Ilaria Vespoli, B.Sc., M.Sc.
• Incompatibility : MC270P61A, MC270P76, MC270P80, MC280P66B
• In complex pre-requisite: MC270C92, MC270C93

Annotation

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

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.

Literature

Last update: PharmDr. Eliška Matoušová, Ph.D. (23.05.2022)

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

Requirements to the exam

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

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%.

Syllabus

Last update: PharmDr. Eliška Matoušová, Ph.D. (17.02.2022)

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.