INTERNATIONAL   CHEMISTRY  OLYMPIAD

PROGRAM

 

                                                        SYLLABUS OF THE INTERNATIONAL CHEMISTRY OLYMPIAD
Level 1: These topics are included in the overwhelming majority of secondary school chemistry programs and need not to be mentioned in the preparatory problems.
Level 2: These topics are included in a substantial number of secondary school programs and maybe used without exemplification in the preparatory
problems.
Level 3: These topics are not included in the majority of secondary school programs and can only be used in the competition if examples are given in the preparatory problems.

1 INORGANIC CHEMISTRY

1. 1 Electronic configuration of atoms and ions
1.1.1 main groups             1
1.1.2 transition metals             2
1.1.3 lanthanide and actinide metals             3
1.1.4 Pauli exclusion principle             1
1.1.5 Hund's rule             1

1.2 Trends in the periodic table (main groups)
1.2.1 electronegativity         1
1.2.2 electron affinity         2
1.2.3 first ionization energy         2
1.2.4 atomic size         1
1.2.5 ionic size         2
1.2.6 highest oxidation number         1

1.3 Trends in physical properties (main groups)
1.3.1 melting point         1
1.3.2 boiling point         1
1.3.3 metal character         1
1.3.4 magnetic properties         2
1.3.5 thermal properties         3
1.3.6 law of Dulong and Petit         1
1.3.7 electrical conductivity         3

1.4 Structures
1.4.1 simple molecular structures         2
1.4.2 simple molecular structures with central atom exceeding octet rule         3
1.4.3 ionic crystal structures         3
1.4.4 metal structures         3
1.4.5 stereochemistry         3

1.5 Nomenclature
1.5.1 oxidation number         1
1.5.2 main group compounds         1
1.5.3 transition metal compounds         1
1.5.4 simple metal complexes         2
1.5.5 multicenter metal complexes         3

1.6 Chemical calculations
1.6.1 balancing equations         1
1.6.2 stoichiometric calculations         1
1.6.3 mass and volume relations         1
1.6.4 empirical formula         1
1.6.5 Avogadro's number         1
1.6.6 concentration calculations         1

1.7 Isotopes
1.7.1 counting of nucleons         1
1.7.2 radioactive decay         1
1.7.3 nuclear reactions (alpha, beta, gamma, neutrino) .         2

1.8 Natural cycles
1.8.1 nitrogen .         2
1.8.2 oxygen         2
1.8.3 carbon         2

1.9 s-Block
1.9.1 Products of reactions of group I and II metals
1.9.1.1 with water, basicity of the products         1
1.9.1.2 with halogens         1
1.9.1.3 with oxygen         2
1.9.2 heavier s-block elements are more reactive         1
1.9.3 lithium combines with H2 and N2 forming LiH and Li3N         2

1.10 p-Block
1.10.1 stoichiometry of simplest non-metal hydrides         1
1.10.2 properties of metal hydrides         3
1.10.3 acid-base properties of CH4, NH3, H2O, H2S, and hydrogen halides HX         1
1.10.4 NO reacts with O2 to form NO2,         1
1.10.5 equilibrium between NO2 and N2O4         1
1.10.6 products of reaction of NO2 with water         1
1.10.7 HNO2 and its salts are reductants         1
1.10.8 HNO3 and its salts are oxidants         1
1.10.9 N2H4 is a liquid and reductant         3
1.10.10 there exist acids like H2N2O2, HN3         3
1.10.11 reactions of HNO3 with different metals and reductants         3
1.10.12 reaction of Na2S2O3 with iodine         2
1.10.13 other thioacids, polyacids, peroxoacids         3
1.10.14 B(III), Al(III), Si(IV), P(V), S(IV), S(VI), O(-II), F(-I), Cl(-I), Cl(I), Cl(III), Cl(V), Cl(VII) are normal oxidation states
of 2nd and 3rd row elements in compounds with halogens and in oxoanions         1
1.10.15 compounds of non-metals with other oxidation states         3
1.10.16 the preferred oxidation states are Sn(II), Pb(II) and Bi(III)         2
1.10.17 products of reactions of non-metal oxides with water and stoichiometry of resulting acids         1
1.10.18 reactions of halogens with water         2
1.10.19 reactivity and oxidizing power of halogens decrease from F2 to I2         1
1.10.20 differences of chemistry between row 4 and row 3 elements         3

1.11 d-Block
1.11.1 common oxidation states of the common d-block metals are Cr(III), Cr(VI), Mn(II), Mn(IV), Mn(VII), Fe(II), Fe(III), Co(II),
Ni(II), Cu(I), Cu(II), Ag(I), Zn(II), Hg(I), and Hg(II)         1
1.11.2 colours of the listed common ions in aqueous solutions         2
1.11.3 other oxidation states and chemistry of other d-block elements         3
1.11.4 Cr, Mn, Fe, Co, Ni, Zn dissolve in dilute HCl; Cu, Ag, Hg do not dissolve         1
1.11.5 products of dissolution are (2+) cations         2
1.11.6 passivation of Cr, Fe (and also Al)         2
1.11.7 Cr(OH)3 and Zn(OH)2 are amphoteric, other common hydroxides are not         1
1.11.8 MnO4- , CrO42- , Cr2O7 2- are strong oxidants         1
1.11.9 products of reduction of MnO4 - depending on pH         2
1.11.10 polyaions other than Cr2O72-         3

1.12 Other inorganic problems
1.12.1 industrial production of H2SO4, NH3, Na2CO3, Na, Cl2, NaOH,         1
1.12.2 chemistry of lanthanides and actinides         3
1.12.3 chemistry of noble gases         3

2. PHYSICAL CHEMISTRY
2.1 Chemical equilibria
2.1.1 dynamical model of chemical equilibrium         1
2.1.2 chemical equilibria expressed in terms of relative concentrations         1
2.1.3 chemical equilibria expressed in terms of partial pressures         2
2.1.4 the relationship between equilibrium constants for ideal gases expressed in different ways (concentration, pressure, mole fraction)     3
2.1.5 relation of equilibrium constant and standard Gibbs energy         3

2.2 Ionic equilibria
2.2.1 Arrhenius theory of acids and bases         1
2.2.2 Broensted-Lowry theory, conjugated acids and bases         1
2.2.3 definition of pH         1
2.2.4 ionic product of water         1
2.2.5 relation between Ka and Kb for conjugated acids and bases         1
2.2.6 hydrolysis of salts         1
2.2.7 solubility product - definition         1
2.2.8 calculation of solubility (in water) from solubility product         1
2.2.9 calculation of pH for weak acid from Ka         1
2.2.10 calculation of pH for 10 -7 mol dm -3 HCl solution         2
2.2.11 calculation of pH for multiprotic acids         2
2.2.12 calculation of pH for weak acid mixtures         3
2.2.13 definition of activity coefficient         2
2.2.14 definition of ionic strength         3
2.2.15 Debye-Huckel formula         3

2.3 Electrode equilibria
2.3.1 electromotive force (definition)         1
2.3.2 first kind electrodes         1
2.3.3 standard electrode potential         1
2.3.4 Nernst equation         2
2.3.5 second kind electrodes         2
2.3.6 relation between ƒ¢ G and electromotive force         3

2.4 Kinetics of homogeneous reactions
2.4.1 factors influencing reaction rate         1
2.4.2 rate equation         1
2.4.3 rate constant         1
2.4.4 order of reactions         2
2.4.5 1st order reactions: time dependence of concentration         2
2.4.6 1st order reactions: half life         2
2.4.7 1st order reactions: relation between half-life and rate constant         2
2.4.8 rate-determining step         2
2.4.9 molecularity         2
2.4.10 Arrhenius equation, activation energy (definition)         2
2.4.11 calculation of rate constant for 1st order reaction         2
2.4.12 calculation of rate constant for second, third order reaction         3
2.4.13 calculation of activation energy from experimental data         3
2.4.14 basic concepts of collision theory         3
2.4.15 basic concepts of transition state theory         3
2.4.16 opposing, parallel and consecutive reactions         3

2.5 Thermodynamics (First law)
2.5.1 system and its surroundings         2
2.5.2 energy, heat and work         2
2.5.3 relation between enthalpy and energy         2
2.5.4 heat capacity - definition         2
2.5.5 difference between Cp and Cv (ideal gas only)         2
2.5.6 Hess law         2
2.5.7 Born-Haber cycle for ionic compounds         3
2.5.8 lattice energies - approximate calculations (e.g. Kapustinski equation)         3
2.5.9 use of standard formation enthalpies         2     
2.5.10 heats of solution and solvation         2
2.5.11 bond energies - definition and uses         2

2.6 Thermodynamics (Second law)
2.6.1 entropy, definition (q/T)         2
2.6.2 entropy and disorder         2
2.6.3 relation S = k ln W         3
2.6.4 relation ƒ¢ G = ƒ¢ H - T ƒ¢ S         2
2.6.5 ƒ¢ G and directionality of changes         2

2.7 Phase systems
2.7.1 ideal gas law         1
2.7.2 van der Waals gas law         3
2.7.3 definition of partial pressure         1
2.7.4 temperature dependence of the vapour pressure of liquid         2
2.7.5 Clausius-Clapeyron equation         3
2.7.6 reading phase diagrams: triple point         3
2.7.7 phase diagrams: critical temperature         3
2.7.8 liquid-vapour system (diagram)         3
2.7.9 liquid-vapour: ideal and non-ideal systems         3
2.7.10 liquid-vapour: use in fractional distillation         3
2.7.11 Henry's law         2
2.7.12 Raoult's law         2
2.7.13 deviations from Raoult's law          3
2.7.14 boiling point elevation law         2
2.7.15 freezing point depression, determination of molar mass         2
2.7.16 osmotic pressure         2
2.7.17 partition coefficient         3
2.7.18 solvent extraction         3
2.7.19 basic principles of chromatography         2

3. ORGANIC CHEMISTRY

3.1 Alkanes
3.1.1 isomers of butane         1
3.1.2 naming (IUPAC)         1
3.1.3 trends in physical properties         1
3.1.4 substitution (e.g. with Cl2)
3.1.4.1 products         1
3.1.4.2 free radicals         2
3.1.4.3 initiation/termination of the chain reaction         2

3.2 Cycloalkanes
3.2.1 names         1
3.2.2 strain in small rings         2
3.2.3 chair/boat conformation         2

3.3 Alkenes
3.3.1 planarity         1
3.3.2 E/Z (cis-trans) isomerism         1

3.3.3 Addition of Br2 and HBr
3.3.3.1 products         1
3.3.3.2 Markovnikoff's rule         2
3.3.3.3 carbonium ions in addition reaction         3
3.3.3.4 relative stability of carbonium ions         3
3.3.3.5 1,4-addition to alkadiene         3

3.4 Alkynes
3.4.1 linear geometry         1
3.4.2 acidity         2
3.4.3 differences in chemical properties between alkenes and alkynes         3

3.5 Arenes and heterocycles
3.5.1 formula of benzene         1
3.5.2 delocalization of electrons         1
3.5.3 stabilization by resonance         1
3.5.4 Huckel (4n + 2) rule         3
3.5.5 aromaticity of heterocycles         3
3.5.6 nomenclature of heterocycles (IUPAC)         3
3.5.7 polycyclic aromatic compounds         3
3.5.8 effect of first substituent on reactivity         2
3.5.9 effect of first substituent on direction of substitution          2
3.5.10 explanation of substituent effects         3

3.6 Halogen compounds
3.6.1 hydrolytic reactions         2
3.6.2 exchange of halogens         3
3.6.3 reactivity (primary vs secondary vs tertiary)         2
3.6.4 ionic mechanism of substitution         2
3.6.5 side products (elimination)         2
3.6.6 reactivity (aliphatic vs aromatic)         2
3.6.7 Wurtz (RX + Na) reaction         3
3.6.8 halogen derivatives and pollution         3

3.7 Alcohols and phenols
3.7.1 hydrogen bonding - alcohols vs ethers         1
3.7.2 acidity of alcohols vs phenols         2
3.7.3 dehydration to alkenes         1
3.7.4 dehydration to ethers         2
3.7.5 esters with inorganic acids         2
3.7.6 iodoform reaction         2
3.7.7 reactions of primary/secondary/tertiary: Lucas reagent         2
3.7.8 formula of glycerin         1

3.8 Carbonyl compounds
3.8.1 nomenclature         1
3.8.2 keto/enol tautomerism         2

3.8.3 Preparation of carbonyl compounds
3.8.3.1 oxidation of alcohols         1
3.8.3.2 from carbon monoxide         3

3.8.4 Reaction of carbonyl compounds
3.8.4.1 oxidation of aldehydes         1
3.8.4.2 reduction with Zn metal         2
3.8.4.3 addition of HCN         2
3.8.4.4 addition of NaHSO3         2
3.8.4.5 addition of NH2OH         2
3.8.4.6 aldol condensation         3
3.8.4.7 preparation of acetates         2
3.8.4.8 Cannizzaro (PhCH2OH disproportionation)         3
3.8.4.9 Grignard reaction         2
3.8.4.10 Fehling (Cu2O) and Tollens (Ag mirror)         2

3.10 Carboxylic acids
3.10.1 inductive effect and strength         2
3.10.2 equivalence of oxygen atoms in anions         2

3.10.3 Preparation and reactions of carboxylic acids
3.10.3.1 preparation from esters         2
3.10.3.2 preparation from nitriles         2
3.10.3.3 products of reaction with alcohols (esters)         1
3.10.3.4 mechanism of esterification         2
3.10.3.5 isotopes in mechanism elucidation         3
3.10.3.6 nomenclature of acid halides         2
3.10.3.7 preparation of acid chlorides         2
3.10.3.8 preparation of amides from acid chlorides         2
3.10.3.9 preparation of nitriles from acid chlorides         3
3.10.3.10 properties and preparation of anhydrides         2
3.10.3.11 oxalic acid, name and formula         1
3.10.3.12 multifunctional acids (e.g. hydroxyacids, ketoacids)         2
3.10.3.13 polycarboxylic acids         2
3.10.3.14 optical activity (e.g. lactic acid         2
3.10.3.15 R/S nomenclature         3
3.10.3.16 plant and animal fats, differences         2

3.11 Nitrogen compounds
3.11.1 basicity of amines         1
3.11.2 comparing aliphatic vs aromatic         2
3.11.3 names: primary, secondary, tertiary, quaternary amines         2
3.11.4 identification of primary/sec./tert./quaternary amines in laboratory         3

3.11.5 Preparation of amines
3.11.5.1 from halogen compounds         2
3.11.5.2 from nitro compounds (e.g. PhNH2 from PhNO2)         3
3.11.5.3 from amides (Hoffmann)         3

3.11.6 mechanism of Hoffmann rearrangement in acidic/basic medium         3
3.11.7 basicity amines vs amides         2
3.11.8 diazotation products of aliphatic amines         3
3.11.9 diazotation products of aromatic amines         3
3.11.10 dyes: colour vs structure (chromophore groups)         3
3.11.11 nitro compounds : aci/nitro tautomerism         3
3.11.12 Beckmann (oxime - amide) rearrangements         3

3.12 Some large molecules
3.12.1 hydrophilic/hydrophobic groups         2
3.12.2 micelle structure         3
3.12.3 preparation of soaps         1
            products of polymerization of:
3.12.4 - styrene         2
3.12.5 - ethene         1
3.12.6 - polyamides         3
3.12.7 - phenol + aldehydes         3
3.12.8 - polyuretanes         3
3.12.9 polymers cross linking         3
3.12.10 chain mechanism of polymer formation         2
3.12.11 rubber composition         3

4. BIOCHEMISTRY

4.1 Aminoacids and peptides
4.1.1 ionic structure of aminoacids         1
4.1.2 isoelectric point         2
4.1.3 20 aminoacids (classification in groups)         2
4.1.4 20 aminoacids (names and structures)         3
4.1.5 ninhydrin reaction (including equation)         3
4.1.6 separation by chromatography         3
4.1.7 separation by electrophoresis         3
4.1.8 peptide linkage         1

4.2 Proteins
4.2.1 primary structure of proteins         1
4.2.2 -S-S- bridges         3
4.2.3 sequence analysis         3
4.2.4 secondary structures         3
4.2.5 details of alpha-helix structure         3
4.2.6 tertiary structure         3
4.2.7 denaturation reaction by change of pH, temperature, metals, ethanol         2
4.2.8 quaternary structure         3
4.2.9 separation of proteins (molecule size and solubility)         3
4.2.10 metabolism of proteins (general)         3
4.2.11 proteolysis         3
4.2.12 transamination         3
4.2.13 four pathways of catabolism of amino acids         3
4.2.14 decarboxylation of amino acids         3
4.2.15 urea cycle (only results)         3

4.3 Fatty acids and fats
4.3.1 IUPAC names from C4 to C18         2
4.3.2 trivial names of most important (ca. 5) fatty acids         2
4.3.3 general metabolism of fats         2
4.3.4 beta-oxidation of fatty acids (formulas and ATP balance)         3
4.3.5 fatty acids and fats anabolism         3
4.3.6 phosphoglycerides         3
4.3.7 membranes         3
4.3.8 active transport         3

4.4 Enzymes
4.4.1 general properties, active centres         2
4.4.2 nomenclature, kinetics, coenzymes, function of ATP, etc.         3
4.5 Saccharides
        glucose and fructose:
4.5.1 - chain formulas         2
4.5.2 - Fischer projections         2
4.5.3 - Haworth formulas         3
4.5.4 osazones         3
4.5.5 maltose as reducing sugar         2
4.5.6 difference between starch and cellulose         2
4.5.7 difference between alpha- and beta-D glucose         2
4.5.8 metabolism from starch to acetyl-CoA         3
4.5.9 pathway to lactic acid or to ethanol; catabolism of glucose         3
4.5.10 ATP balance for the above pathways         3
4.5.11 photosynthesis (products only)         2
4.5.12 light and dark reaction         3
4.5.13 detailed Calvin cycle         3

4.6 Krebs cycle and respiration chain
4.6.1 formation of CO2 in the cycle (no details)         3
4.6.2 intermediate compounds in the cycle         3
4.6.3 formation of water and ATP (no details)         3
4.6.4 FMN and cytochromes         3
4.6.5 calculation of ATP amount for 1 mole of glucose         3

4.7 Nucleic acids and protein synthesis
4.7.1 pyrimidine, purine         2
4.7.2 nucleosides and nucleotides         3
4.7.3 formulas of all pyrimidine and purine bases         3
4.7.4 difference between ribose and 2-deoxyribose         3
4.7.5 base combination CG and AT         3
4.7.6 base combination CG and AT - (hydrogen bonding structure)         3
4.7.7 difference between DNA and RNA         3
4.7.8 difference between mRNA and tRNA         3
4.7.9 hydrolysis of nucleic acids         3
4.7.10 semiconservative replication of DNA         3
4.7.11 DNA-ligase         3
4.7.12 RNA synthesis (transcription) without details         3
4.7.13 reverse transcriptase         3
4.7.14 use of genetic code         3
4.7.15 start and stop codons         3
4.7.16 translation steps         3

4.8 Other biochemical problems
4.8.1 hormones, regulation         3
4.8.2 hormones, feedback         3
4.8.3 insulin, glucagon, adrenaline         3
4.8.4 mineral metabolism (no details)         3
4.8.5 ions in blood         3
4.8.6 buffers in blood         3
4.8.7 haemoglobin; function and skeleton         3
4.8.8 haemoglobin; diagram of oxygen absorption         3
4.8.9 steps in clotting the blood         3
4.8.10 antigens and antibodies         3
4.8.11 blood groups         3
4.8.12 acetyl choline, structure and functions         3

OTHER PROBLEMS

5. Analytical chemistry

5.1 choice of indicators for acidimetry         1
5.2 titration curve; pH (strong and weak acid)         2
5.3 EMF (redox titration)         2
5.4 calculation of pH of simple buffer solution         2
5.5 identification of Ag + , Ba 2+ , Cl - , SO4 2-         1
5.6 identification of Al 3+ , NO2 - , NO3 - , Bi 3+         2
5.7 identification of VO3 - , ClO3 - , Ti 4+ 3
5.8 use of flame tests for identification of K, Ca a Sr         1
5.9 Beer-Lambert law         2

6. Complexes

6.1 writing down complexation reactions         1
6.2 definition of coordination number         1
6.3 prediction of coordination number of complex ions and molecules         3
6.4 complex formation constants (definition)         2
6.5 Eg and T2g terms: high and low spin octahedral complexes         3
6.6 calculation of solubility of AgCl in NH3 (from Ks and constants ƒÀ )         3
6.7 cis and trans forms 3

7. Theoretical chemistry

7.1 energy levels of hydrogen atom (formula)     2
7.2 square of the wave function and probability         3
7.3 understanding the simplest Schrodinger equation         3
7.4 n, l, m quantum numbers         2
7.5 shape of p-orbitals         2
7.6 d orbital stereoconfiguration         3
7.7 molecular orbital diagram: H2 molecule         2
7.8 molecular orbital diagram: N2 and O2 molecules         3
7.9 bond orders in O2, O2 + , O2 -         3
7.10 unpaired electrons and paramagnetism         2
7.11 Huckel theory for aromatic compounds         3
7.12 Lewis acids and bases         2
7.13 hard and soft Lewis acids         3

8. Instrumental methods of determining structure

8.1 UV-VIS spectroscopy
8.1.1 identification of aromatic compound     3
8.1.2 identification of chromophore         3

8.2 Mass spectra
        recognition of:
8.2.1 - molecular ion         3
8.2.2 - fragments with a help of a table         3
8.2.3 typical isotope distribution         3

8.3 Infrared spectra
8.3.1 interpretation using a table of group frequencies         3
8.3.2 recognition of hydrogen bonds         3
8.3.3 Raman spectroscopy         3

8.4 NMR
8.4.1 interpretation of simple spectrum (like ethanol)         3
8.4.2 spin-spin coupling         3
8.4.3 coupling constants         3
8.4.4 identification of o- and p- substituted benzene         3
8.4.5 13 C- NMR         3

8.5 X-rays
8.5.1 Bragg law         3
8.5.2 electron density diagram         3
8.5.3 coordination number         3
8.5.4 unit cell         3
        structures:
8.5.5 - of NaCl         3
8.5.6 - of CsCl         3
8.5.7 - close-packed (2 types)         3
8.5.8 determining of the Avogadro constant from X-ray data         3

8.6 Polarimetry
8.6.1 calculation of specific rotation angle         3