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IChO Chemistry Olympiad 2019-51 Preparatory Problems Solutions

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Chemistry Olympiad Problems with Solutions

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  • March 6, 2023
  • 148
  • 2019/2020
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PREPARATORY
PROBLEMS




Making science together!



Third edition (19-6-3)

,Table of contents

Preface ........................................................................................................................................ 3
Fields of advanced difficulty ...................................................................................................... 5
Theoretical problems ............................................................................................................. 10
Problem 1. Butadiene π-electron system .................................................................................. 11
Problem 2. Localization and delocalization in benzene ........................................................... 13
Problem 3. Study of liquid benzene hydrogenation ................................................................. 15
Problem 4. Use of dihydrogen: fuel cells ................................................................................. 16
Problem 5. Hydrogen storage ................................................................................................... 18
Problem 6. Deacidification and desulfurization of natural gas ................................................ 22
Problem 7. Lavoisier’s experiment .......................................................................................... 25
Problem 8. Which wine is it? Blind tasting challenge ............................................................. 26
Problem 9. Nitrophenols: synthesis and physical properties .................................................... 27
Problem 10. French stone flower ............................................................................................. 31
Problem 11. The mineral of winners ........................................................................................ 33
Problem 12. Reaction progress kinetics ................................................................................... 34
Problem 13. Nylon 6 ................................................................................................................ 37
Problem 14. Synthesis of block copolymers followed by size-exclusion chromatography ..... 39
Problem 15. Radical polymerization ........................................................................................ 43
Problem 16. Biodegradable polyesters ..................................................................................... 46
Problem 17. Vitrimers .............................................................................................................. 48
Problem 18. A kinetic study of the Maillard reaction .............................................................. 50
Problem 19. Glycosidases and inhibitors ................................................................................. 53
Problem 20. Fluoro-deoxyglucose and PET imaging .............................................................. 56
Problem 21. Catalysis and stereoselective synthesis of cobalt glycocomplexes ...................... 61
Problem 22. Structural study of copper (II) complexes ........................................................... 62
Problem 23. Synthesis and study of a molecular motor ........................................................... 64
Problem 24. Some steps of a synthesis of cantharidin ............................................................. 67
Problem 25. Study of ricinoleic acid ........................................................................................ 68
Problem 26. Synthesis of oseltamivir ....................................................................................... 70
Problem 27. Formal synthesis of testosterone .......................................................................... 71
Back to 1990: Aqueous solutions of copper salts .................................................................... 73
Practical problems .................................................................................................................. 74
Problem P1: Synthesis of dibenzylideneacetone ...................................................................... 75
Problem P2: Oxidation of (‒)-borneol to (‒)-camphor ............................................................ 77
Problem P3: Aspirin® tablet ..................................................................................................... 79
Problem P4: Illuminated Europe .............................................................................................. 81
Problem P5: Protecting the vineyard ........................................................................................ 83
Problem P6: Equilibrium constant determination .................................................................... 86




51st IChO – Preparatory problems 2

,Preface
We are happy to provide Preparatory Problems for the 51st International Chemistry Olympiad.
These problems will be an opportunity for students to train for the Olympiad, but also to
discover numerous topics in both modern and traditional chemistry. These problems should be
solved using the topics covered in high school and some topics of advanced difficulty listed
below (six for the theoretical part and two for the practical one).
This booklet contains 27 theoretical and 6 practical problems. Its length should not be seen as
an indication of its difficulty: it merely reflects our commitment to write these problems in a
spirit as similar as possible to the final problems. An additional theoretical task (Back to 1990)
ends the first section. This problem should not be studied as thoroughly as the others, as it is an
excerpt of the tasks proposed to the candidates during the last Olympiad held in France, in 1990.
The official solutions will be sent to the Head Mentors by the end of February 2019, and will
be published on the IChO 2019 website not earlier than the 1st of June 2019.
We will be happy to read and reply to your comments, corrections and questions about the
problems. Please send them to contact-icho2019@laligue.org

Looking forward to seeing you in Paris to enjoy chemistry and to make science together!




The members of the Scientific Committee in charge of the preparatory problems

Didier Bourissou, CNRS, Toulouse
Aurélien Moncomble, Université de Lille
Élise Duboué-Dijon, CNRS, Paris
Clément Guibert, Sorbonne Université, Paris
Baptiste Haddou, Lycée Darius Milhaud, Le Kremlin-Bicêtre
Hakim Lakmini, Lycée Saint Louis, Paris




Acknowledgments

We would like to thank all the authors for their efforts in writing these problems. Their hard
work during numerous months resulted in this booklet that will hopefully be useful for the
young chemists involved in this Olympiad. We are also indebted to the reviewers, including the
members of the steering committee, whose precision and thoroughness significantly improved
these problems.




51st IChO – Preparatory problems 3

, Contributing authors

Pierre Aubertin, Lycée Léonard de Vinci, Calais Laurent Heinrich, Lycée Pierre Corneille, Rouen
Tahar Ayad, Chimie ParisTech, Paris Lucas Henry, ENS, Paris
Alex Blokhuis, ESPCI, Paris Claire Kammerer, Univ. Paul Sabatier, Toulouse
Clément Camp, CNRS, Lyon Dmytro Kandaskalov, Aix Marseille Université
Jean-Marc Campagne, ENSCM, Montpellier Iuliia Karpenko, Université de Strasbourg
Xavier Cattoën, CNRS, Grenoble Maxime Lacuve, ENSAM, Paris
Baptiste Chappaz, Collège Les Pyramides, Évry Hakim Lakmini, Lycée Saint Louis, Paris
Sylvain Clède, Lycée Stanislas, Paris Julien Lalande, Lycée Henri IV, Paris
Éric Clot, CNRS, Montpellier Alix Lenormand, Lycée Henri Poincaré, Nancy
Olivier Colin, UVSQ, Versailles Étienne Mangaud, Univ. Paul Sabatier, Toulouse
Bénédicte Colnet, Mines ParisTech, Paris Jean-Daniel Marty, Univ. Paul Sabatier, Toulouse
Antton Curutchet, ENS Lyon Olivier Maury, CNRS, Lyon
Élise Duboué-Dijon, CNRS, Paris Bastien Mettra, IUT-Lyon1, Villeurbanne
Alain Fruchier, ENSCM, Montpellier Aurélien Moncomble, Université de Lille
Ludivine Garcia, Lycée Jean Moulin, Béziers Pierre-Adrien Payard, ENS, Paris
Catherine Gautier, Lycée Algoud Laffemas, Valence Daniel Pla, CNRS, Toulouse
Didier Gigmes, CNRS, Marseille Romain Ramozzi, Lycée Henri Poincaré, Nancy
Emmanuel Gras, CNRS, Toulouse Clémence Richaud, Lycée Jules Verne, Limours
Laetitia Guerret, ENS Paris-Saclay, Cachan Vincent Robert, Université de Strasbourg
Clément Guibert, Sorbonne Université, Paris Jean-Marie Swiecicki, MIT, Cambridge (USA)
Dayana Gulevich, Moscow State University Guillaume Vives, Sorbonne Université, Paris
Baptiste Haddou, Lycée D. Milhaud, Kremlin-Bicêtre Hanna Zhdanova, Université de Strasbourg

Additional reviewers

Lucile Anthore-Dalion Guillaume Mériguet
Olivier Durupthy
Quentin Arnoux Mathilde Niocel
Matthieu Emond
Marie Auvray Artem Osypenko
Johanna Foret
Simon Beaumont Valentin Quint
Mickaël Four
Nicolas Bolik-Coulon Emelyne Renaglia
Emma Gendre
Jérémy Camponovo Tristan Ribeyre-Stecki
Isabelle Girard
Natan Capobianco Clément Robert
Antoine Hoste
Antoine Carof Nell Saunders
Damien Lavergne
Guillaume Carret Laura Scalfi
Quentin Lefebvre
Fabrice Dalier Freddy Szymczak
Christina Legendre
Guillaume Didier Julien Valentin
Anne Leleu
Philippe Drabent Dominique Vichard
Marion Livecchi
Laurence Dupont Vincent Wieczny




51st IChO – Preparatory problems 4

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