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Physical organic chemistry explores how the chemical structure of organic compounds influences their reactivity, utilizing physical and chemical approaches. In this field, students gain insights into the physical and mechanistic aspects of organic reactions, delving into areas such as thermodynamics, kinetics, and spectroscopy. A key focus is on the experimental methodologies employed to decipher the mechanisms driving organic reactions, as well as understanding the thermodynamics and kinetics of these reactions and the role of reaction media. Central to this study is the application of quantitative relationships between structure and reactivity, particularly through linear free energy correlations.
Last update: Krupička Martin (18.12.2023)
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Upon successful completion of this course, the student will be able to:
Understand and apply the basic principles and methods of physical organic chemistry.
Analyze the relationships between the structure and reactivity of organic compounds.
Describe and explain the mechanisms of organic reactions based on thermodynamic and kinetic data.
Utilize spectroscopic methods to monitor the progress of reactions.
Design experiments that investigate the physical and mechanistic aspects of organic reactions.
Interpret the results of experiments in the context of physical organic chemistry and propose further procedures. Last update: Krupička Martin (18.12.2023)
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Student performance will be evaluated through a written exam consisting of open-ended questions and problems requiring calculations. This approach assesses students' understanding of the course material, their ability to apply concepts practically, and their analytical skills. The exam will include questions that necessitate the use of a pocket calculator for computations, alongside theoretical questions demanding clear, well-reasoned responses. Last update: Krupička Martin (18.12.2023)
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Recommended: Eric V. Anslyn, Dennis A. Dougherty : Modern Physical Organic Chemistry. 1891389319 Last update: Krupička Martin (18.12.2023)
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1. Chemical Bonding Theory - Orbitals, hybridization, molecular orbitals, orbitals of functional groups and reactive intermediates.
2. Thermochemistry and Stability - Free energy, bond energy, relationship between structure and reactivity, conformation, electronic effects, contributory methods.
3. Non-covalent Interactions - Interaction types, solvent behavior, solubility, thermodynamics of solutions and supramolecules, molecular recognition.
4. Acids and Bases - Acidity in aqueous and non-aqueous solutions and concentrated acids, predicting acidity and basicity.
5. Stereochemistry - Relative and absolute configuration, topology, dynamic stereochemistry.
6. Kinetics - Potential energy surface, transition state theory, kinetic analysis.
7. Experimental Thermodynamics and Kinetics - Isotopic effects, substitution effects, Linear Free Energy Relationships (LFER).
8. Catalysis - General principles, acid and base catalysis, enzymatic catalysis, organocatalysis.
9. Pericyclic Reactions - Orbital symmetry, cycloadditions, electrocyclic reactions, rearrangements.
10. Isomerizations and Rearrangements - Migrations to carbon and heteroatoms, carbanionic and radical rearrangements.
11. Photochemistry - Mechanisms and processes, Jablonski diagram.
12. Reactive Intermediates - Structure and reactivity, carbocations, carbanions, radicals, carbenes.
13. Organic Reactivity 1 - Mechanisms, their confirmation, and dependence on structure: a. Nucleophiles and electrophiles, acids and bases, orbital interactions. b. Electrophilic, nucleophilic, and radical additions. c. Ester hydrolysis. d. Elimination.
14. Organic Reactivity 2 - Mechanisms, their confirmation, and dependence on structure: a. Addition-elimination mechanisms, SEAr, SNAr, SRN1. b. Aliphatic substitution, SN1, SN2, neighboring group effects. c. Radical substitution. Last update: Krupička Martin (18.12.2023)
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Textbook, lecture notes in e-learning Last update: Krupička Martin (18.12.2023)
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Organic Reaction Mechanisms Physical Chemistry Last update: Krupička Martin (18.12.2023)
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