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Lecturer(s)
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Pospíšil Jiří, doc. PhD.
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Vychodilová Kristýna, Ing. Ph.D.
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Course content
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The lesson will cover the following six categories. 1. Definition (to be sure we speak about the same things) a. Classification of organic reactions, definition of how-to-write-down the things, etc. b. Substrate, reagent, catalyst, etc. 2. Equilibrium and kinetics a. Enthalpy vs. Entropy (Gibbs Free Energy, Arrhenius Equation, etc.) b. Reaction order - single and double one c. Hammond principle, principle of microscopic reversibility d. Thermodynamically controlled reactions e. HSAB principle, Bronsted's acid vs. Lewis acids, general and specific acid catalysis, catalysis 3. Relationship between structure and reactivity a. Atomic and molecular orbits i. Focus on elements with s, p, d orbitals ii. Electronegativity and polarity of bonds; polarizability of atoms and bonds b. Molecular orbitals i. HOMO, LUMO and SOMO ii. Influence of substitution and heteroatoms c. Effect of substituents on the reaction i. Steric ii. Hammett's and Taft's equations d. Isotope effect i. Primary vs. Secondary; utility in study of the reactions 4. Molecules in the space - influence of spatial arrangement of the molecule on its reactivity and/or influence of the molecule on stereochemical outcome of the reaction. a. Conformation i. Anomeric effect, hyperconjugation, mutation, epimerization ii. Influence of conformational equilibria on reaction, Curtin-Hammet principle b. Reaction coordinates i. Stereospecific vs. Stereoselective reactions ii. Elimination iii. Nucleophilic substitutions c. Reactions on chiral substrates i. Additives to carbonyl and individual models 5. Spectroscopic methods a. Which methods can help us in analyzing the structure to determine substrate reactivity 6. Reactive intermediates a. Carbocations, carbanions, carbines (carbenoids), nitrates
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Learning activities and teaching methods
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Lecture, Dialogic Lecture (Discussion, Dialog, Brainstorming)
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Learning outcomes
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The aim of the course is to teach students to apply their knowledge of stereochemistry (structure of atoms in molecules in 3D space), reaction mechanisms (description of organic reactions) and physical chemistry to evaluate organic molecules in the context of their reactivity. Within the subject, the student is guided to realize that in organic chemistry all processes are in equilibrium. With this basic postulate and knowledge of the elementary concepts of kinetics, thermodynamics, statistical and dynamic stereochemistry and conformational analysis, students should develop their understanding and evaluation of the reactivity of organic substrates. The emphasis will be given to the understanding the influence of electronic and steric effects of individual functional groups on the reactivity of organic molecules.
Be able to evaluate organic compounds from the point of view of their structure and to evaluate the influence of functional groups on the reactivity of given compounds. o Be able to interpret the relationship in qualitative and quantitative terms. o Based on the foregoing analysis and interpretation, be able to influence or completely change/reverse the original reactivity of the substrate.
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Prerequisites
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Basic knowledge in the field of organic, inorganic, and physical chemistry.
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Assessment methods and criteria
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Mark, Written exam, Written exam
Credit: Test at the end of the semester, which must be passed at 60%. This test will serve as the basis for the test. Exam: Based on credit test. According to the test result, you will have the starting position for the oral exam as follows (indicated for the converted results to 20/20 (100%): number of points - 12.0-14.0 (E); 14.1-16.0 ( D); 16.1-18.0 (C); 18.1-19.5 (B); 19.5-20.0 (A).
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Recommended literature
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F. A. Carey, R. J. Sundberg. (2007). Advanced organic chemistry. Part A, Structure and mechanisms. New York, N.Y., Springer, 5th ed.
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G. Rothenberg. (2008). Catalysis : concepts and green applications. Weinheim,Wiley-VCH.
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K. A. Savin. (2014). Writing reaction mechanisms in organic chemistry. Waltham, Mass., Academic Press.
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P. Atkins, J. de Paula. (2010). Atkins' physical chemistry. Oxford : Oxford University Press.
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