C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is taught annually.
Listed among pre-requisites of other courses
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Spring 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Spring 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2007 - for the purpose of the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.

C5500 Stereochemistry of Organic Compounds

Faculty of Science
Autumn 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
The course is also listed under the following terms Autumn 2010 - only for the accreditation, Autumn 2000, Autumn 2001, Autumn 2002, Spring 2004, Spring 2005, Autumn 2005, Autumn 2006, Autumn 2007, Autumn 2008, Autumn 2009, Autumn 2010, Autumn 2011, Autumn 2011 - acreditation, Autumn 2012, Autumn 2013, Autumn 2014, Autumn 2015, Autumn 2016, autumn 2017, Autumn 2018, Autumn 2019, Autumn 2020, autumn 2021, Autumn 2022, Autumn 2023, Autumn 2024.
  • Enrolment Statistics (recent)