C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2024
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
In-person direct teaching - Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Wed 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2023
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2022
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Wed 17:00–18:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of Scienceautumn 2021
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Wed 9:00–10:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2020
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 15:00–16:50 prace doma
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2019
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 15 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Learning outcomes
- Student will understand concept of isomerism of chemical compounds;
will be able to work with concepts conformation, configuration, chirality and optical activity;
will be able to chose suitable methods for identification of stereoisomers, determination of their contents in mixtures, and their possible separation;
utilize symmetry for elucidation of heterotopicity of homomorphic ligands and faces;
recognize stereoselective reactions and explain reasons of their selectivity based on steric, stereoelectronic and further effects;
utilize basic chiroptic methods for analysis and identification of chiral compounds. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- recommended literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- not specified
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2018
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Mon 17. 9. to Fri 14. 12. Wed 12:00–13:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of Scienceautumn 2017
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Mon 18. 9. to Fri 15. 12. Wed 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- English
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2016
- Extent and Intensity
- 2/0/0. 2 credit(s) (plus extra credits for completion). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- doc. RNDr. Ctibor Mazal, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Mon 19. 9. to Sun 18. 12. Wed 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2015
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 15:00–16:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2014
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Wed 14:00–15:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2013
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 14:00–15:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2012
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science
Supplier department: Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 9:00–10:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2011
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 9:00–10:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2010
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Fri 10:00–11:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2009
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Wed 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2008
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 13:00–14:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Assessment methods
- Lecture;
oral exam follows a written test. - Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2007
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Tue 16:00–17:50 A08/309
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus (in Czech)
- 1. Struktura. Význam, způsoby popisu struktury, vnitřní souřadnice. Konstituce, konfigurace a konformace. Způsoby určování struktury. 2. Stereoisomerie. Hlavní typy stereoisomerů. Energetické vymezení stereoisomerů. Residuální stereoisomery. Diastereomery a enantiomery. 3. Úvod do symetrie. Prvky symetrie, operátory symetrie a bodové grupy symetrie. Vztah chirality a symetrie. Vztah symetrie a molekulárních vlastností. Stáčení roviny polarizovaného světla, dipólový moment. 4. Konfigurace. Definice absolutní a relativní konfigurace. Nomenklaturní vyjádření absolutní a relativní konfigurace. Metody určování absolutní a relativní konfigurace. 5. Vlastnosti stereoisomerů. Rozlišení stereoisomerů. Vlastnosti racemátů a jejich enentiomerních složek. Metody určování enantiomerního a diastereomerního složení, časová škála experimentu (chiroptické metody, NMR, chromatografie a pod.). 6. Separace stereoisomerů. Separace enantiomerů krystalizací, chemickými metodami přes diastereomery. Kinetická resoluce. Racemizace. 7. Homotopické a heterotopické ligandy a strany, prostereoisomerie a prochiralita. Enantiotopicita, diastereotopicita. Heterotopicita a NMR, anisochronie a anisogamie. 8. Stereochemie alkenů. Alkeny s nízkými rotačními barierami, neplanární alkeny. Dvojné vazby C=N a N=N. Určování konfigurace isomerů chemickými a fyzikálními metodami. Metody interkonverze cis- trans isomerů. 9. Konformace nasycených a nenasycených acyklických sloučenin. Nasycené acyklické molekuly s polárními substituenty - anomerní efekt. Diastereomerní rovnováhy v acyklických systémech. Fyzikální a spektrální vlastnosti diastereomerů a konformerů. Konformace a reaktivita. Winsteinova-Holnesova rovnice a Curtiův-Hammettův princip. 10. Konformace a konfigurace cyklických molekul. Určování konfigurace substituovaných kruhů. Stabilita cyklických molekul. Pnutí kruhu, snadnost cyklizace v závislosti na velikosti kruhu a povaze reakčních center, Baldwinova pravidla. Konformační aspekty chemie monocyklických a polycyklických sloučenin, stereoelektronické efekty. 11. Stereoselektivní syntéza. Základy terminologie, kategorie stereoslektivní syntézy. Strategie řízení stereochemie v diastereoselektivní a enantioselektivní syntéze. Využití chirálních neracemických reagentů a katalyzátorů. 12. Chiroptické vlastnosti. Optická aktivita. Anisotropní refrakce, Optická rotační disperse (ORD). Anisotropní absorpce, Cirkulární dichroismus (CD). Využití CD a ORD při určování konfigurace a konformace. Polarimetrie, empirická pravidla a korelace. 13. Chiralita molekul bez center chirality. Nomenklatura. Alleny, spirany, atropoisomerie způsobená zábranou rotace kolem jednoduché vazby. Heliceny. Planární chiralita (Cyklofány, anuleny, metaloceny a d.). Kryptostereoisomerie.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- Study Materials
The course is taught annually. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2006
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Timetable
- Thu 16:00–17:50 03021
- Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus (in Czech)
- 1. Struktura. Význam, způsoby popisu struktury, vnitřní souřadnice. Konstituce, konfigurace a konformace. Způsoby určování struktury. 2. Stereoisomerie. Hlavní typy stereoisomerů. Energetické vymezení stereoisomerů. Residuální stereoisomery. Diastereomery a enantiomery. 3. Úvod do symetrie. Prvky symetrie, operátory symetrie a bodové grupy symetrie. Vztah chirality a symetrie. Vztah symetrie a molekulárních vlastností. Stáčení roviny polarizovaného světla, dipólový moment. 4. Konfigurace. Definice absolutní a relativní konfigurace. Nomenklaturní vyjádření absolutní a relativní konfigurace. Metody určování absolutní a relativní konfigurace. 5. Vlastnosti stereoisomerů. Rozlišení stereoisomerů. Vlastnosti racemátů a jejich enentiomerních složek. Metody určování enantiomerního a diastereomerního složení, časová škála experimentu (chiroptické metody, NMR, chromatografie a pod.). 6. Separace stereoisomerů. Separace enantiomerů krystalizací, chemickými metodami přes diastereomery. Kinetická resoluce. Racemizace. 7. Homotopické a heterotopické ligandy a strany, prostereoisomerie a prochiralita. Enantiotopicita, diastereotopicita. Heterotopicita a NMR, anisochronie a anisogamie. 8. Stereochemie alkenů. Alkeny s nízkými rotačními barierami, neplanární alkeny. Dvojné vazby C=N a N=N. Určování konfigurace isomerů chemickými a fyzikálními metodami. Metody interkonverze cis- trans isomerů. 9. Konformace nasycených a nenasycených acyklických sloučenin. Nasycené acyklické molekuly s polárními substituenty - anomerní efekt. Diastereomerní rovnováhy v acyklických systémech. Fyzikální a spektrální vlastnosti diastereomerů a konformerů. Konformace a reaktivita. Winsteinova-Holnesova rovnice a Curtiův-Hammettův princip. 10. Konformace a konfigurace cyklických molekul. Určování konfigurace substituovaných kruhů. Stabilita cyklických molekul. Pnutí kruhu, snadnost cyklizace v závislosti na velikosti kruhu a povaze reakčních center, Baldwinova pravidla. Konformační aspekty chemie monocyklických a polycyklických sloučenin, stereoelektronické efekty. 11. Stereoselektivní syntéza. Základy terminologie, kategorie stereoslektivní syntézy. Strategie řízení stereochemie v diastereoselektivní a enantioselektivní syntéze. Využití chirálních neracemických reagentů a katalyzátorů. 12. Chiroptické vlastnosti. Optická aktivita. Anisotropní refrakce, Optická rotační disperse (ORD). Anisotropní absorpce, Cirkulární dichroismus (CD). Využití CD a ORD při určování konfigurace a konformace. Polarimetrie, empirická pravidla a korelace. 13. Chiralita molekul bez center chirality. Nomenklatura. Alleny, spirany, atropoisomerie způsobená zábranou rotace kolem jednoduché vazby. Heliceny. Planární chiralita (Cyklofány, anuleny, metaloceny a d.). Kryptostereoisomerie.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
- Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2005
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus (in Czech)
- 1. Struktura. Význam, způsoby popisu struktury, vnitřní souřadnice. Konstituce, konfigurace a konformace. Způsoby určování struktury. 2. Stereoisomerie. Hlavní typy stereoisomerů. Energetické vymezení stereoisomerů. Residuální stereoisomery. Diastereomery a enantiomery. 3. Úvod do symetrie. Prvky symetrie, operátory symetrie a bodové grupy symetrie. Vztah chirality a symetrie. Vztah symetrie a molekulárních vlastností. Stáčení roviny polarizovaného světla, dipólový moment. 4. Konfigurace. Definice absolutní a relativní konfigurace. Nomenklaturní vyjádření absolutní a relativní konfigurace. Metody určování absolutní a relativní konfigurace. 5. Vlastnosti stereoisomerů. Rozlišení stereoisomerů. Vlastnosti racemátů a jejich enentiomerních složek. Metody určování enantiomerního a diastereomerního složení, časová škála experimentu (chiroptické metody, NMR, chromatografie a pod.). 6. Separace stereoisomerů. Separace enantiomerů krystalizací, chemickými metodami přes diastereomery. Kinetická resoluce. Racemizace. 7. Homotopické a heterotopické ligandy a strany, prostereoisomerie a prochiralita. Enantiotopicita, diastereotopicita. Heterotopicita a NMR, anisochronie a anisogamie. 8. Stereochemie alkenů. Alkeny s nízkými rotačními barierami, neplanární alkeny. Dvojné vazby C=N a N=N. Určování konfigurace isomerů chemickými a fyzikálními metodami. Metody interkonverze cis- trans isomerů. 9. Konformace nasycených a nenasycených acyklických sloučenin. Nasycené acyklické molekuly s polárními substituenty - anomerní efekt. Diastereomerní rovnováhy v acyklických systémech. Fyzikální a spektrální vlastnosti diastereomerů a konformerů. Konformace a reaktivita. Winsteinova-Holnesova rovnice a Curtiův-Hammettův princip. 10. Konformace a konfigurace cyklických molekul. Určování konfigurace substituovaných kruhů. Stabilita cyklických molekul. Pnutí kruhu, snadnost cyklizace v závislosti na velikosti kruhu a povaze reakčních center, Baldwinova pravidla. Konformační aspekty chemie monocyklických a polycyklických sloučenin, stereoelektronické efekty. 11. Stereoselektivní syntéza. Základy terminologie, kategorie stereoslektivní syntézy. Strategie řízení stereochemie v diastereoselektivní a enantioselektivní syntéze. Využití chirálních neracemických reagentů a katalyzátorů. 12. Chiroptické vlastnosti. Optická aktivita. Anisotropní refrakce, Optická rotační disperse (ORD). Anisotropní absorpce, Cirkulární dichroismus (CD). Využití CD a ORD při určování konfigurace a konformace. Polarimetrie, empirická pravidla a korelace. 13. Chiralita molekul bez center chirality. Nomenklatura. Alleny, spirany, atropoisomerie způsobená zábranou rotace kolem jednoduché vazby. Heliceny. Planární chiralita (Cyklofány, anuleny, metaloceny a d.). Kryptostereoisomerie.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceSpring 2005
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus (in Czech)
- 1. Struktura. Význam, způsoby popisu struktury, vnitřní souřadnice. Konstituce, konfigurace a konformace. Způsoby určování struktury. 2. Stereoisomerie. Hlavní typy stereoisomerů. Energetické vymezení stereoisomerů. Residuální stereoisomery. Diastereomery a enantiomery. 3. Úvod do symetrie. Prvky symetrie, operátory symetrie a bodové grupy symetrie. Vztah chirality a symetrie. Vztah symetrie a molekulárních vlastností. Stáčení roviny polarizovaného světla, dipólový moment. 4. Konfigurace. Definice absolutní a relativní konfigurace. Nomenklaturní vyjádření absolutní a relativní konfigurace. Metody určování absolutní a relativní konfigurace. 5. Vlastnosti stereoisomerů. Rozlišení stereoisomerů. Vlastnosti racemátů a jejich enentiomerních složek. Metody určování enantiomerního a diastereomerního složení, časová škála experimentu (chiroptické metody, NMR, chromatografie a pod.). 6. Separace stereoisomerů. Separace enantiomerů krystalizací, chemickými metodami přes diastereomery. Kinetická resoluce. Racemizace. 7. Homotopické a heterotopické ligandy a strany, prostereoisomerie a prochiralita. Enantiotopicita, diastereotopicita. Heterotopicita a NMR, anisochronie a anisogamie. 8. Stereochemie alkenů. Alkeny s nízkými rotačními barierami, neplanární alkeny. Dvojné vazby C=N a N=N. Určování konfigurace isomerů chemickými a fyzikálními metodami. Metody interkonverze cis- trans isomerů. 9. Konformace nasycených a nenasycených acyklických sloučenin. Nasycené acyklické molekuly s polárními substituenty - anomerní efekt. Diastereomerní rovnováhy v acyklických systémech. Fyzikální a spektrální vlastnosti diastereomerů a konformerů. Konformace a reaktivita. Winsteinova-Holnesova rovnice a Curtiův-Hammettův princip. 10. Konformace a konfigurace cyklických molekul. Určování konfigurace substituovaných kruhů. Stabilita cyklických molekul. Pnutí kruhu, snadnost cyklizace v závislosti na velikosti kruhu a povaze reakčních center, Baldwinova pravidla. Konformační aspekty chemie monocyklických a polycyklických sloučenin, stereoelektronické efekty. 11. Stereoselektivní syntéza. Základy terminologie, kategorie stereoslektivní syntézy. Strategie řízení stereochemie v diastereoselektivní a enantioselektivní syntéze. Využití chirálních neracemických reagentů a katalyzátorů. 12. Chiroptické vlastnosti. Optická aktivita. Anisotropní refrakce, Optická rotační disperse (ORD). Anisotropní absorpce, Cirkulární dichroismus (CD). Využití CD a ORD při určování konfigurace a konformace. Polarimetrie, empirická pravidla a korelace. 13. Chiralita molekul bez center chirality. Nomenklatura. Alleny, spirany, atropoisomerie způsobená zábranou rotace kolem jednoduché vazby. Heliceny. Planární chiralita (Cyklofány, anuleny, metaloceny a d.). Kryptostereoisomerie.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceSpring 2004
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods. 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers. 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment). 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration. 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition. 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization. 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony. 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers. 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle. 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect. 11. Stereoselective synthesis. 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation. 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2002
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- prof. RNDr. Jaroslav Jonas, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Prerequisites
- Organic Chemistry I and II Physical Chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 23 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus
- 1.Pasteur and vant Hoff - two different ways to stereoochemistry. Symmetry-based and constitution-based approaches. Topological stereochemistry. 2. Inner coordinates of molecular structure, their changes through intramolecular dynamics and the corresponding energy landscape. Configuration and conformation. 3. Symmetry, asymmetry, dissymetry, and chirality. Molecular and local symmetry and point group classification thereof. 4. Local symmetry and stereogenicity. Prochirality and prostereogenicity. Symmetry of a dynamic molecular structure in relation to experimental time scale. 5. Isomerism and topicity with static molecular structures. Classification and methods of analysis. 6. Isomerism and topicity with dynamic molecular structures. Time scale of spectroscopic methods - especially NMR. 7. Absolute and relative configuration - methods for determination. 8. Racemic modifications, their separation into enantiomers. 9. Stereisomerism of acyclic and cyclic systems due to rotation around single bonds. 10. Stereoelectronic effects, especially the anomeric effect. 11. Stereoisomerism due to multiple bonds. 12.Stereodifferentiating reactions - classification and general considerations. 13. Stereodifferentiating reactions exemplified. 14. Stereochemistry of penta- and hexacoordinated compounds as compared to tetra-coordination. Stereochemical methodology - an overview.
- Literature
- Eliel E. L., Wilen S.H., Doyle M.P.: Basic Organic Stereochemistry, Wiley 2001, 704 pp., ISBN 0-471-37499-7
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Assessment methods (in Czech)
- A lecture interspersed with seminar - oral examination.
- Language of instruction
- English
- Further comments (probably available only in Czech)
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2001
- Extent and Intensity
- 2/0/0. 4 credit(s). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- prof. RNDr. Jaroslav Jonas, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Prerequisites
- Organic Chemistry I and II Physical Chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 23 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus
- 1.Pasteur and vant Hoff - two different ways to stereoochemistry. Symmetry-based and constitution-based approaches. Topological stereochemistry. 2. Inner coordinates of molecular structure, their changes through intramolecular dynamics and the corresponding energy landscape. Configuration and conformation. 3. Symmetry, asymmetry, dissymetry, and chirality. Molecular and local symmetry and point group classification thereof. 4. Local symmetry and stereogenicity. Prochirality and prostereogenicity. Symmetry of a dynamic molecular structure in relation to experimental time scale. 5. Isomerism and topicity with static molecular structures. Classification and methods of analysis. 6. Isomerism and topicity with dynamic molecular structures. Time scale of spectroscopic methods - especially NMR. 7. Absolute and relative configuration - methods for determination. 8. Racemic modifications, their separation into enantiomers. 9. Stereisomerism of acyclic and cyclic systems due to rotation around single bonds. 10. Stereoelectronic effects, especially the anomeric effect. 11. Stereoisomerism due to multiple bonds. 12.Stereodifferentiating reactions - classification and general considerations. 13. Stereodifferentiating reactions exemplified. 14. Stereochemistry of penta- and hexacoordinated compounds as compared to tetra-coordination. Stereochemical methodology - an overview.
- Literature
- Eliel E. L., Wilen S.H., Doyle M.P.: Basic Organic Stereochemistry, Wiley 2001, 704 pp., ISBN 0-471-37499-7
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Assessment methods (in Czech)
- A lecture interspersed with seminar - oral examination.
- Language of instruction
- English
- Further comments (probably available only in Czech)
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2000
- Extent and Intensity
- 2/0/0. 4 credit(s). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- prof. RNDr. Jaroslav Jonas, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Chemistry Section – Faculty of Science - Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 23 fields of study the course is directly associated with, display
- Language of instruction
- English
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2011 - acreditation
The information about the term Autumn 2011 - acreditation is not made public
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2010 - only for the accreditation
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Main objectives can be summarized as follows:
to discuss basic principles of organic stereochemistry with preference to to a symmetry-based approach to structures, ligands, faces and reaction classification;
to understand chirality as a condition sine qua non for enantiomerism and enantiodifferentiation;
to discuss the time-dimension in connection with intramolecular dynamism and time-scale of instrumental methods;
to point out problems of the origin of homochirality in living systems;
to learn about topological stereochemistry. - Syllabus
- 1. Structure. Meaning, description of structure, constitution, configuration and conformation. Structure determination methods.
- 2. Stereoisomers. Diastereomers and enantiomers. Energy barriers and residual stereoisomers.
- 3. Symmetry. Symmetry elements and operators, symmetry point groups. Chirality and symmetry. Symmetry and molecular properties (rotation of polarized light, dipole moment).
- 4. Configuration. Relative and absolute configuration. Notation. Determination of absolute and relative configuration.
- 5. Stereoisomers discrimination. Properties of racemates and their enantiomer components. Determination of enantiomer and diastreomer composition.
- 6. Separation of stereoisomers, resolution. Crystallization, chromatography, chemical separation methods via diastereomers. Kinetic resolution. Racemization.
- 7. Homotopic and heterotopic ligands and faces. Prostereoisomerism and prochirality. Enantiotopicity and diastereotopicity. Heterotopicity and NMR, anisochrony.
- 8. Stereochemistry of molecules with double bond. Alkenes. The C=N and N=N double bonds. Determination of isomer configuration, chemical and physical methods. Interconversion of isomers.
- 9. Conformation of acyclic saturated and unsaturated compounds. Generalized anomeric effect. Conformation and physical and spectral properties of molecules and their reactivity. Winstein-Holness equation. Curtin-Hammett principle.
- 10. Conformation and configuration of cyclic molecules. Determination of configuration of substituted rings. Stability of cyclic molecules. Baldwin rules. Conformational aspects of chemistry of some ring compounds (six- and five-membered rings). Anomeric effect.
- 11. Stereoselective synthesis.
- 12. Chiroptical properties. Optical rotatory dispersion (Cotton effect). Circular dichroism. Application of chiroptical methods to determination of configuration and conformation.
- 13. Chirality of molecules devoid of chiral centers. Axial and planar chirality. Nomenclature. Allenes, Spiranes and others. Atropoisomerism, biphenyls and others. Helicenes. Cyclophanes and other molecules with planar chirality.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Teaching methods
- Lectures
- Assessment methods
- Oral exam follows a written test.
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
C5500 Stereochemistry of Organic Compounds
Faculty of ScienceAutumn 2007 - for the purpose of the accreditation
- Extent and Intensity
- 2/0/0. 2 credit(s) (fasci plus compl plus > 4). Recommended Type of Completion: zk (examination). Other types of completion: k (colloquium).
- Teacher(s)
- doc. RNDr. Ctibor Mazal, CSc. (lecturer)
- Guaranteed by
- prof. RNDr. Jaroslav Jonas, CSc.
Department of Chemistry – Chemistry Section – Faculty of Science - Prerequisites
- Organic chemistry I and II
- Course Enrolment Limitations
- The course is also offered to the students of the fields other than those the course is directly associated with.
- fields of study / plans the course is directly associated with
- there are 21 fields of study the course is directly associated with, display
- Course objectives
- Basic principles of organic stereochemistry will be highlighted and discussed. Preference will be given to a symmetry-based approach to structures, ligands, faces and reactions classification. Chirality will be discussed as a condition sine qua non for enantiomerism and enantiodifferentiation. The time-dimension will be thoroughly discussed in connection with intramolecular dynamism and time-scale of instrumental methods. Problems of the origin of homochirality in living systems will be pointed out and topological stereochemistry will be mentioned.
- Syllabus (in Czech)
- 1. Struktura. Význam, způsoby popisu struktury, vnitřní souřadnice. Konstituce, konfigurace a konformace. Způsoby určování struktury. 2. Stereoisomerie. Hlavní typy stereoisomerů. Energetické vymezení stereoisomerů. Residuální stereoisomery. Diastereomery a enantiomery. 3. Úvod do symetrie. Prvky symetrie, operátory symetrie a bodové grupy symetrie. Vztah chirality a symetrie. Vztah symetrie a molekulárních vlastností. Stáčení roviny polarizovaného světla, dipólový moment. 4. Konfigurace. Definice absolutní a relativní konfigurace. Nomenklaturní vyjádření absolutní a relativní konfigurace. Metody určování absolutní a relativní konfigurace. 5. Vlastnosti stereoisomerů. Rozlišení stereoisomerů. Vlastnosti racemátů a jejich enentiomerních složek. Metody určování enantiomerního a diastereomerního složení, časová škála experimentu (chiroptické metody, NMR, chromatografie a pod.). 6. Separace stereoisomerů. Separace enantiomerů krystalizací, chemickými metodami přes diastereomery. Kinetická resoluce. Racemizace. 7. Homotopické a heterotopické ligandy a strany, prostereoisomerie a prochiralita. Enantiotopicita, diastereotopicita. Heterotopicita a NMR, anisochronie a anisogamie. 8. Stereochemie alkenů. Alkeny s nízkými rotačními barierami, neplanární alkeny. Dvojné vazby C=N a N=N. Určování konfigurace isomerů chemickými a fyzikálními metodami. Metody interkonverze cis- trans isomerů. 9. Konformace nasycených a nenasycených acyklických sloučenin. Nasycené acyklické molekuly s polárními substituenty - anomerní efekt. Diastereomerní rovnováhy v acyklických systémech. Fyzikální a spektrální vlastnosti diastereomerů a konformerů. Konformace a reaktivita. Winsteinova-Holnesova rovnice a Curtiův-Hammettův princip. 10. Konformace a konfigurace cyklických molekul. Určování konfigurace substituovaných kruhů. Stabilita cyklických molekul. Pnutí kruhu, snadnost cyklizace v závislosti na velikosti kruhu a povaze reakčních center, Baldwinova pravidla. Konformační aspekty chemie monocyklických a polycyklických sloučenin, stereoelektronické efekty. 11. Stereoselektivní syntéza. Základy terminologie, kategorie stereoslektivní syntézy. Strategie řízení stereochemie v diastereoselektivní a enantioselektivní syntéze. Využití chirálních neracemických reagentů a katalyzátorů. 12. Chiroptické vlastnosti. Optická aktivita. Anisotropní refrakce, Optická rotační disperse (ORD). Anisotropní absorpce, Cirkulární dichroismus (CD). Využití CD a ORD při určování konfigurace a konformace. Polarimetrie, empirická pravidla a korelace. 13. Chiralita molekul bez center chirality. Nomenklatura. Alleny, spirany, atropoisomerie způsobená zábranou rotace kolem jednoduché vazby. Heliceny. Planární chiralita (Cyklofány, anuleny, metaloceny a d.). Kryptostereoisomerie.
- Literature
- WILEN, Samuel H. and Michael P. DOYLE. Basic organic stereochemistry. Edited by Ernest Ludwig Eliel. New York: Wiley-Interscience, 2001, xiv, 688. ISBN 0471374997. info
- WILEN, Samuel H. and Lewis N. MANDER. Stereochemistry of organic compounds. Edited by Ernest Ludwig Eliel. New York: John Wiley & Sons, 1993, xv, 1267. ISBN 0471016705. info
- JONAS, Jaroslav and Ctibor MAZAL. Konspekt ze základů organické stereochemie (Conspect of Basic Organic Stereochemistry). 1st ed. Brno: Masarykova univerzita, 2002, 87 pp. ISBN 80-210-2941-2. info
- ELIEL, Ernest Ludwig. Stereochemie uhlíkatých sloučenin. Translated by Miloš Tichý. 1. vyd. Praha: Academia, 1970, 541 s. info
- Language of instruction
- Czech
- Further Comments
- The course is taught annually.
The course is taught: every week. - Listed among pre-requisites of other courses
- Enrolment Statistics (recent)