19th – 29th July 2018
Bratislava, SLOVAKIA
Prague, CZECH REPUBLIC
www.50icho.eu
PREPARATORY PROBLEMS: THEORETICAL
50th IChO 2018
International Chemistry Olympiad
SLOVAKIA & CZECH REPUBLIC
BACK TO WHERE IT ALL BEGAN
UPDATED 1st JUNE 2018
,INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Table of Contents
Preface....................................................................................................................................... 2
Contributing Authors................................................................................................................... 3
Fields of Advanced Difficulty ...................................................................................................... 4
Physical Constants and Equations ............................................................................................. 5
Periodic Table of Elements ......................................................................................................... 7
Visible Light Spectrum ................................................................................................................ 8
Problem 1. Synthesis of hydrogen cyanide ................................................................................. 9
Problem 2. Thermochemistry of rocket fuels............................................................................. 10
Problem 3. HIV protease .......................................................................................................... 12
Problem 4. Enantioselective hydrogenation .............................................................................. 14
Problem 5. Ultrafast reactions .................................................................................................. 15
Problem 6. Kinetic isotope effects ............................................................................................ 17
Problem 7. Designing a photoelectrochemical cell.................................................................... 19
Problem 8. Fuel cells ................................................................................................................ 22
Problem 9. Acid-base equilibria in blood ................................................................................... 24
Problem 10: Ion exchange capacity of a cation exchange resin................................................ 25
Problem 11. Weak and strong cation exchange resin ............................................................... 26
Problem 12: Uranyl extraction .................................................................................................. 27
Problem 13. Determination of active chlorine in commercial products ...................................... 29
Problem 14. Chemical elements in fireworks ............................................................................ 30
Problem 15. Colours of complexes ........................................................................................... 31
Problem 16. Iron chemistry ....................................................................................................... 33
Problem 17. Cyanido- and fluorido-complexes of manganese .................................................. 37
Problem 18. The fox and the stork ............................................................................................ 39
Problem 19. Structures in the solid state .................................................................................. 42
Problem 20. Cyclobutanes ....................................................................................................... 44
Problem 21. Fluorinated radiotracers........................................................................................ 45
Problem 22. Where is lithium? .................................................................................................. 47
Problem 23. Synthesis of eremophilone ................................................................................... 48
Problem 24. Cinnamon all around ............................................................................................ 50
Problem 25. All roads lead to caprolactam ............................................................................... 53
Problem 26. Ring opening polymerization (ROP) ..................................................................... 54
Problem 27. Zoniporide ............................................................................................................ 56
Problem 28. Nucleic acids ........................................................................................................ 60
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 1
,INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Preface
We are happy to introduce the Preparatory Problems for the 50th International Chemistry
Olympiad. These problems are intended to make the preparation for the Olympiad easier for both
students and their mentors. The problems we prepared cover a wide range of challenging topics
in modern chemistry. We based the problems on subjects typically covered in high school
chemistry courses as well as six topics of advanced difficulty for the Theoretical part and two
topics of advanced difficulty for the Practical part. These topics are listed under “Topics of
Advanced Difficulty”, and their applications are shown in the preparatory problems. Based on our
experience, each of these topics can be introduced to well-prepared students in two to three
hours.
The solutions will be sent to the head mentor of each country by email by 15th February 2018 and
will be published online on 1st June 2018. We welcome any comments, corrections and questions
about the problems via email at .
We wish you a lot of fun solving the problems and we look forward to seeing you in July
in Bratislava and Prague.
Acknowledgment
We would like to thank all the authors for their hard and dedicated work on both the preparatory
and competition problems. We are also grateful to the reviewers for their valuable comments and
suggestions.
Bratislava and Prague, 30th January 2018
On behalf of the Scientific Committee,
Petra Ménová and Martin Putala
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 2
, INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Contributing Authors
Ctirad Červinka University of Chemistry and Technology, Prague
Tomáš Fiala Columbia University, New York, USA
Ivana Gergelitsová University of Chemistry and Technology, Prague
Petr Holzhauser University of Chemistry and Technology, Prague
Jakub Hraníček Charles University, Prague
Martin Hrubý Institute of Macromolecular Chemistry, CAS, Prague
Vít Jakeš University of Chemistry and Technology, Prague
Jan Kotek Charles University, Prague
Michal H. Kolář Max Planck Institute for Biophysical Chemistry, Göttingen, Germany
Matouš Krömer Institute of Organic Chemistry and Biochemistry, CAS, Prague
Tomáš Kubař Karlsruhe Institute of Technology, Germany
Jaroslav Kvíčala University of Chemistry and Technology, Prague
Alan Liška J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Tomáš Mahnel University of Chemistry and Technology, Prague
Radek Matuška Secondary Technical School of Chemistry, Brno
Petra Ménová University of Chemistry and Technology, Prague
Lukáš Mikulů University of Chemistry and Technology, Prague
Petr Motloch University of Cambridge, UK
Eva Muchová University of Chemistry and Technology, Prague
Roman Nebel J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Tomáš Neveselý University of Chemistry and Technology, Prague
Pavla Perlíková Institute of Organic Chemistry and Biochemistry, CAS, Prague
Eva Pluhařová J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Kateřina Rubešová University of Chemistry and Technology, Prague
Pavel Řezanka University of Chemistry and Technology, Prague
Petr Slavíček University of Chemistry and Technology, Prague
Ondřej Šimůnek University of Chemistry and Technology, Prague
Tomáš Tobrman University of Chemistry and Technology, Prague
Kamil Záruba University of Chemistry and Technology, Prague
Edited by
Petra Ménová University of Chemistry and Technology, Prague
Martin Putala Comenius University in Bratislava
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 3
Bratislava, SLOVAKIA
Prague, CZECH REPUBLIC
www.50icho.eu
PREPARATORY PROBLEMS: THEORETICAL
50th IChO 2018
International Chemistry Olympiad
SLOVAKIA & CZECH REPUBLIC
BACK TO WHERE IT ALL BEGAN
UPDATED 1st JUNE 2018
,INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Table of Contents
Preface....................................................................................................................................... 2
Contributing Authors................................................................................................................... 3
Fields of Advanced Difficulty ...................................................................................................... 4
Physical Constants and Equations ............................................................................................. 5
Periodic Table of Elements ......................................................................................................... 7
Visible Light Spectrum ................................................................................................................ 8
Problem 1. Synthesis of hydrogen cyanide ................................................................................. 9
Problem 2. Thermochemistry of rocket fuels............................................................................. 10
Problem 3. HIV protease .......................................................................................................... 12
Problem 4. Enantioselective hydrogenation .............................................................................. 14
Problem 5. Ultrafast reactions .................................................................................................. 15
Problem 6. Kinetic isotope effects ............................................................................................ 17
Problem 7. Designing a photoelectrochemical cell.................................................................... 19
Problem 8. Fuel cells ................................................................................................................ 22
Problem 9. Acid-base equilibria in blood ................................................................................... 24
Problem 10: Ion exchange capacity of a cation exchange resin................................................ 25
Problem 11. Weak and strong cation exchange resin ............................................................... 26
Problem 12: Uranyl extraction .................................................................................................. 27
Problem 13. Determination of active chlorine in commercial products ...................................... 29
Problem 14. Chemical elements in fireworks ............................................................................ 30
Problem 15. Colours of complexes ........................................................................................... 31
Problem 16. Iron chemistry ....................................................................................................... 33
Problem 17. Cyanido- and fluorido-complexes of manganese .................................................. 37
Problem 18. The fox and the stork ............................................................................................ 39
Problem 19. Structures in the solid state .................................................................................. 42
Problem 20. Cyclobutanes ....................................................................................................... 44
Problem 21. Fluorinated radiotracers........................................................................................ 45
Problem 22. Where is lithium? .................................................................................................. 47
Problem 23. Synthesis of eremophilone ................................................................................... 48
Problem 24. Cinnamon all around ............................................................................................ 50
Problem 25. All roads lead to caprolactam ............................................................................... 53
Problem 26. Ring opening polymerization (ROP) ..................................................................... 54
Problem 27. Zoniporide ............................................................................................................ 56
Problem 28. Nucleic acids ........................................................................................................ 60
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 1
,INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Preface
We are happy to introduce the Preparatory Problems for the 50th International Chemistry
Olympiad. These problems are intended to make the preparation for the Olympiad easier for both
students and their mentors. The problems we prepared cover a wide range of challenging topics
in modern chemistry. We based the problems on subjects typically covered in high school
chemistry courses as well as six topics of advanced difficulty for the Theoretical part and two
topics of advanced difficulty for the Practical part. These topics are listed under “Topics of
Advanced Difficulty”, and their applications are shown in the preparatory problems. Based on our
experience, each of these topics can be introduced to well-prepared students in two to three
hours.
The solutions will be sent to the head mentor of each country by email by 15th February 2018 and
will be published online on 1st June 2018. We welcome any comments, corrections and questions
about the problems via email at .
We wish you a lot of fun solving the problems and we look forward to seeing you in July
in Bratislava and Prague.
Acknowledgment
We would like to thank all the authors for their hard and dedicated work on both the preparatory
and competition problems. We are also grateful to the reviewers for their valuable comments and
suggestions.
Bratislava and Prague, 30th January 2018
On behalf of the Scientific Committee,
Petra Ménová and Martin Putala
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 2
, INTERNATIONAL CHEMISTRY OLYMPIAD / SLOVAKIA & CZECH REPUBLIC, 2018
Contributing Authors
Ctirad Červinka University of Chemistry and Technology, Prague
Tomáš Fiala Columbia University, New York, USA
Ivana Gergelitsová University of Chemistry and Technology, Prague
Petr Holzhauser University of Chemistry and Technology, Prague
Jakub Hraníček Charles University, Prague
Martin Hrubý Institute of Macromolecular Chemistry, CAS, Prague
Vít Jakeš University of Chemistry and Technology, Prague
Jan Kotek Charles University, Prague
Michal H. Kolář Max Planck Institute for Biophysical Chemistry, Göttingen, Germany
Matouš Krömer Institute of Organic Chemistry and Biochemistry, CAS, Prague
Tomáš Kubař Karlsruhe Institute of Technology, Germany
Jaroslav Kvíčala University of Chemistry and Technology, Prague
Alan Liška J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Tomáš Mahnel University of Chemistry and Technology, Prague
Radek Matuška Secondary Technical School of Chemistry, Brno
Petra Ménová University of Chemistry and Technology, Prague
Lukáš Mikulů University of Chemistry and Technology, Prague
Petr Motloch University of Cambridge, UK
Eva Muchová University of Chemistry and Technology, Prague
Roman Nebel J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Tomáš Neveselý University of Chemistry and Technology, Prague
Pavla Perlíková Institute of Organic Chemistry and Biochemistry, CAS, Prague
Eva Pluhařová J. Heyrovský Institute of Physical Chemistry, CAS, Prague
Kateřina Rubešová University of Chemistry and Technology, Prague
Pavel Řezanka University of Chemistry and Technology, Prague
Petr Slavíček University of Chemistry and Technology, Prague
Ondřej Šimůnek University of Chemistry and Technology, Prague
Tomáš Tobrman University of Chemistry and Technology, Prague
Kamil Záruba University of Chemistry and Technology, Prague
Edited by
Petra Ménová University of Chemistry and Technology, Prague
Martin Putala Comenius University in Bratislava
PREPARATORY PROBLEMS: THEORETICAL www.50icho.eu 3
