35th International Chemistry Olympiad, Athens, Greece, 5-14 July 2003


Last revision: July 2002

1.The atom
1.1.1.Counting of nucleons1
1.2.The hydrogen atom
1.2.1.Concept of energy levels1
1.2.2.Shape of s-orbitals1
1.2.3.(7.5) Shape and orientation of p-orbitals1
1.2.4.(7.6) Shape and orientation of d-orbitals3
1.2.5.(7.3) Understanding the simplest Schrödinger equation3
1.2.6.(7.2) Square of the wave function and probability3
1.2.7.(7.4) Quantum numbers (n, l, ml)3
1.3.1.Types of radioactivity1
1.3.2.Radioactive decay1
1.3.3.Nuclear reactions2
2.Chemical bonding
2.1.VSEPR - Simple molecular structures with
2.1.1.no more than four electron pairs about central atom1
2.1.2.with central atom exceeding the "octet rule"3
2.2.Delocalization and resonance3
2.3.Hybrid orbital theory3
2.4.Molecular orbital theory
2.4.1.(7.7) molecular orbital diagram (H2 molecule)3
2.4.2.(7.8) molecular orbital diagram (N2 and O2 molecules)3
2.4.3.(7.9) bond orders in O2, O2-, O2+3
2.4.4.(7.10) unpaired electrons and paramagnetism3
3.Chemical calculations
3.1.1.(1.6.1) Balancing equations1
3.1.2.(1.6.2) Stoichiometric calculations1
3.1.3.(1.6.3) Mass and volume relations (including density)1
3.1.4.(1.6.4) Empirical fomula1
3.1.5.(1.6.5) Avogadro's number1
3.1.6.(1.6.6) Concentration calculations1
4.Periodic trends
4.1.Electron configuration
4.1.1.(1.1.4) Pauli exclusion principle1
4.1.2.(1.1.5) Hund's Rule1
4.1.3.(1.1.1) Main group elements1
4.1.4.(1.1.2) Transition metal elements1
4.1.5.(1.1.3) Lanthanide and actinide metals3
4.2.(1.2.1) Electronegativity1
4.3.(1.2.2) Electron affinity2
4.4.(1.2.3) First ionization energy1
4.5.(1.2.4) Atomic size1
4.6.(1.2.5) Ion size1
4.7.(1.2.6) Highest oxidation number1
5.Inorganic Chemistry
5.1.1.Trends in physical properties of elements (Main groups) melting point1 boiling point1 metal character1 magnetic properties3 electrical conductivity2
5.1.2.(1.5.1) Oxidation number1
5.1.3.Nomenclature1 (1.5.2) main group compounds1 transition metal compounds1 simple metal complexes3
5.2.Groups 1 and 2
5.2.1.(1.9.2) Trend in reactivity of (heavy elements more reactive)1
5.2.2.Products of reaction with water1 oxygen2
5.2.3.Basicity of oxides1
5.2.4.(1.10.2) Properties of hydrides3
5.2.5.Other compounds, properties and oxidation states3
5.3.Groups 13 - 18 and Hydrogen
5.3.1.Binary molecular compounds of hydrogen Formulae1 Acid-base properties of CH4, NH3, H2O, H2S1 properties3
5.3.2.Group 13 The oxidation state of boron and aluminium in their oxides and chlorides is +31 acid-base properties of aluminium oxide/hydroxide2 of boron(III) oxide with water3 of boron(III) chloride with water3 compounds, properties and oxidation states3
5.3.3.Group 14 The oxidation state of Si in its chloride and oxide is +41 The +2 and +4 oxidation states of carbon tin and lead, the acid-base and redox properties of the oxides and chlorides2 compounds, properties and oxidation states3
5.3.4.Group 15 Phosphorus(+5) oxide and chloride, and their reaction with water2 oxide and chloride, and their reaction with water2 of nitrogen
a(1.10.4) Reaction of NO to form NO21
b(1.10.5) Dimerization of NO21
c(1.10.6) Reaction of NO2 with water1 properties of
a(1.10.8) HNO3 and nitrates1
b(1.10.9 and 7) HNO2 and NH2NH23 Bi(+5) and Bi(+3)3 compounds, properties and oxidation states3
5.3.5.Group 16 The +4 and +6 oxidation states of sulfur, reaction of their oxides with water, properties of their acids1 Reaction of thiosulfate anion with I23 compounds, properties and oxidation states3
5.3.6.Group 17 (Halogens) Reactivity and oxidant strength decreases from F2 to I21 properties of the hydrogen halides1 The oxidation state of fluorine in its compounds is -11 The -1, +1, +3, +5, +7 oxidation states of chlorine1 oxoanions of chlorine2 Reactions of halogens with water3 Reaction of Cl2O and Cl2O7 with water3 compounds, properties and oxidation states3
5.3.7.(1.12.3) Group 183
5.4.Transition elements
5.4.1.(1.11.1) Common oxidation states of common transition metals1
Cr(+2), Cr(+3) Mn(+2), Mn(+4), Mn(+7) Ag(+1)
Fe(+2), Fe(+3) Co(+2) Zn(+2)
Hg(+1), Hg(+2) Cu(+1), Cu(+2) Ni(+2)
5.4.2. (1.11.2) Colours of ions listed above in aqueous solution2
5.4.3.(1.11.4) Insolubility of Ag, Hg and Cu don't in HCl2
5.4.4.(1.11.5) M2+ arising by dissolution of the other metals in HCl2
5.4.5.(1.11.7) Cr(OH)3 and Zn(OH)2 are amphoteric and the other +2 oxides/hydroxides of the metals listed above are basic2
5.4.6.(1.11.8) MnO4- and Cr2O72- are strong oxidants in acid solution1
5.4.7.(1.11.9) pH dependence of products of MnO4- acting as oxidant2
5.4.8.(1.11.10??) Interconversion between CrO42- and Cr2O72-3
5.4.9.Other compounds, properties and oxidation states3
5.5.(1.12.2) Lanthanides and actinides3
5.6.Coordination chemistry including stereochemistry
5.6.1.(6.2) Definition of coordination number1
5.6.2.(6.1) Writing equations for complexation reactions given all formulae1
5.6.3.Formulae of common complex ions complex ions3
5.6.4.(6.5) Ligand field theory (eg and t2g terms, high and low spin)3
5.6.5.Stereochemistry cis and trans3
5.7.Selected industrial processes
5.7.1.(1.12.1) Preparation of H2SO41
5.7.2.(1.12.1) Preparation of NH31
5.7.3.(1.12.1) Preparation of Na2CO32
5.7.4.(1.12.1) Preparation of Cl2 and NaOH2
5.7.5.Preparation of HNO32
6.Physical chemistry
6.1.1.(2.7.1) Ideal gas law1
6.1.2.(2.7.2) van der Waal's gas law3
6.1.3.(2.7.3) definition of partial pressure2
6.1.4.Dalton's Law3
6.2.1.First Law Concept of system and surroundings2 Energy, heat and work2
6.2.2.Enthalpy Relationship between internal energy and enthalpy3 Definition of heat capacity2 Difference between Cp and Cv (ideal gas only)3 That enthalpy is a state property (Hess's Law)2 Born-Haber cycle for ionic compounds3 Use of standard formation enthalpies2 Enthalpies of solution and solvation3 Bond enthalpies (definition and use)2
6.2.3.Second Law (Entropy and Free Energy) Entropy definition (dq/T)3 Entropy and disorder2 Entropy definition (S = k ln W)3 Free energy definition (DG = DH - TDS)3 Using DG to predict direction of natural change3 Relationship of DG0 and equilibrium constant K3
6.3.1.Acid-base Arrhenius definitions of acids and bases1 Brønsted-Lowry definitions,1 conjugate acids and bases1 pH definition1 Kw definition1 Ka as a measure of acid and base strength1 Acidity or basicity of ions1 Calculation of pH from pKa(weak acid)1 Calculation of pH of a simple buffer solution2
6.3.2.Gas phase Equilibrium constant in partial pressures3 Relating Kp and Kc3
6.3.3.Solubility Solubility constant (product) definition (Ks)2 Calculation of solubility in water from Ks2
6.3.4.Compleximetric Complex formation constant (definition)3 involving compleximetric equilibria3 Lewis acids and bases3 Hard and soft Lewis acids and bases3
6.3.5.Phase Temperature dependence of vapour pressure3 Clausius-Clapeyron equation3 component phase diagrams
a(2.7.6) triple point3
b(2.7.7) critical point)3 system
a(2.7.9) ideal and nonideal systems3
b(2.7.8) diagram3
c(2.7.9) use in fractional distillation3 Henry's Law3 Raoult's Law3 Deviation from Raoult's Law3 Boiling point elevation3 Freezing point depression3 Osmotic pressure3 Partition coefficient3 Solvent extraction3
6.3.6.Multiple Calculation of pH for multiprotic acids3 Calculation of pH for weak acid mixtures3
6.4.1.(2.3.1) Electromotive force (definition)1
6.4.2.(2.3.2) First kind electrodes1
6.4.3.(2.3.3) Standard electrode potential1
6.4.4.(2.3.4) Nernst equation3
6.4.5.(2.3.5) Second kind electrodes3
6.4.6.(2.3.6) Relationship between DG and electromotive force3
7.Chemical kinetics (Homogeneous reactions)
7.1.1.(2.4.1) Factors affecting reaction rate1
7.1.2.(2.4.15) Reaction coordinates and the basic idea of a transition state1
7.2.Rate law
7.2.1.(2.4.2) Differential rate law2
7.2.2.(2.4.4) Concept of reaction order2
7.2.3.(2.4.3) Rate constant definition2
7.2.4.First order reactions Dependence of concentration on time3 Concept of half life3 Relationship between half life and rate constant3 Calculation of first order rate constant from
aDifferential rate law3
bIntegrated rate law3 Rate constant for second and third order reactions3
7.3.Reaction mechanisms
7.3.1.(2.4.9) Concept of molecularity3
7.3.2.(2.4.8) Rate-determining step3
7.3.3.(2.4.14) Basic concepts of collision theory3
7.3.4.(2.4.16) Opposing parallel and consecutive reactions3
7.3.5.Arrhenius's law Definition of activation energy3 Calculation of activation energy3
8.1. UV/visible
8.1.1.(8.1.1) Identification of aromatic compound3
8.1.2.(8.1.2) Identification of chromophore3
8.1.3.(3.11.10) Dyes: colour vs structure3
8.1.4.(5.9) Beer's Law3
8.2.1.(8.3.1) Interpretation using a table of frequencies3
8.2.2.(8.3.2) Recognition of hydrogen bonds3
8.3.1.(8.5.1) Bragg's Law3
8.3.2.Concept of coordination number3 unit cell3
8.3.3.Solid structures NaCl3 CsCl3 metals3
8.4.1.General Concepts chemical shift3 spin-spin coupling and coupling constants3
8.4.2.(8.4.1) Interpretation of a simple 1H spectrum (like ethanol)3
8.4.3.(8.4.4) Identification of o- and p-disubstituted benzene3
8.4.4.(8.4.5 +) Interpretation of simple spectra of 13C (proton decoupled) and other spin ½ nuclei3
8.5.Mass spectrometry (8.1.1) Recognition of molecular ion3 Recognition of fragments with the help of a table3 Recognition of typical isotope distribution3
9.Organic Chemistry
9.1.1.(3.1.1) Alkane naming (IUPAC)1
9.1.2.Trends in boiling points of alkanes with structure1 alcohols vs ethers due to hydrogen-bonding1
9.1.3.(3.3.1, 3.4.1) Geometry at singly, doubly, and triply bonded carbon1
9.1.4.Identification of common functional groups1
9.1.5.Isomerism of alkenes cis-trans1 E/Z3
9.1.6.Enantiomers Optical activity2 R/S nomenclature3
9.2.1.Alkanes with halogens
a( products1
b( free radical mechanism (initiation, termination)2
a(3.2.1) names2
b(3.2.2) Strain in small rings3
c(3.2.3) chair/boat conformations of cyclohexane3
9.2.2.Alkenes ( Products from Br2, HBr and H2O/H+1 Markownikoff's rule2 Mechanism involving carbocation intermediates3 Relative stability of carbocations3 1,4 addition to dienes3
9.2.3.Alkynes Acidity relative to alkenes3 Differences in chemical properties from alkenes
9.2.4.Benzene formula1 and 3) stabilization by resonance1 substitution (nitration, halogenation)
a(3.5.9) directing effect of first substituent3
b(3.5.8) effect of first substituent on reactivity3
c(3.5.10) explanation of substituent effects3
9.2.5.Halogen compounds of monofunctional1 Substitution reactions
agiving alcohols3
b(3.6.2) in which halogen is exchanged3
c(3.6.3) reactivity
iprimary vs secondary vs tertiary3
ii(3.6.6) aliphatic vs aromatic3
d (3.6.4) SN1 and SN2 mechanisms3 reactions2 Competition of elimination and substitution2
9.2.6.Alcohols of monofunctional1 Comparison of acidity of alcohols and phenols2 Dehydration to alkenes1 with inorganic acid2 reactions1
9.2.7.Adehydes and ketones of monofunctional1 of aldehydes1 to alcohols (LiAlH4, NaBH4)3 tautomerism3 addition reactions with
bRNH2 (R = alkyl, HO, NH2)3
cenolate anions (aldol condensation)3
dalcohols to form acetals/ketals3
eGrignard reagents3
9.2.8.Carboxylic acids and their derivatives of carboxylic acids and their derivatives (esters, acid halides, amides)2 strength related to inductive effects3 of carboxylic acids by hydrolysis of
aesters (including soaps)1
cnitriles3 of carboxylic acids
awith alcohols to form esters1
bto form acid chlorides3
cto form anhydrides3 of acid chlorides to form amides3 of esterification3 acids (hydroxyacids, ketoacids)3 acids3
asimple amines1
brecognition of primary, secondary, tertiary1
aAs a property of an amine1
bComparison of basicity of aliphatic and aromatic3
cComparison of basicity of amines and amides3
dPreparation of amines
ifrom halides3
iifrom aromatic nitro compounds3
iiifrom amides (by hydrolysis)3
aof aliphatic amines3
bof aromatic amines3
10.1.1.Addition polymers mechanism of formation2
10.1.2.Condensation polymers
10.1.4.Concept of cross-linking and its affect on properties3
11.1.1.Glucose and fructose formulae1 projections2 formulae3
11.1.2.Difference between starch and cellulose2
11.1.3.Difference between a- and b- D glucose2
11.2.1.Structure of fats in relationship to properties2
11.2.2.Formula of glycerol1
11.3.Nitrogen-containing Compounds of Biological Importance
11.3.1.Amino acids structure1 point3 amino acids (classification with structures provided)2 by electrophoresis3 peptide linkage1
11.3.2.Proteins structure1 bridges3 analysis3 structure3 of a helix structure3 structure3 (change in pH, temperature, metals, ethanol)2
11.3.3.Nuclei Acids and Protein Synthesis and purine3 and nucleotides3 of pyrimidine and purine bases3 between ribose and 2-deoxyribose3 combination CG and AT (hydrogen-bonding)3 between DNA and RNA3 between mRNA and tRNA3
11.4.Enzymes properties, active centers3, kinetics, coenzymes, function of ATP3
12.Analytical chemistry
12.1.1.acid-base Titration curve; pH (strong and weak acid)2 Choice of indicators for acidimetry2
12.1.2.(5.3) Redox titration3
12.2.Qualitative analysis
12.2.1.Ions (Inorganic) Identification of Ag+, Ba2+, Cl-, SO42-2 of other anions and cations3
12.2.2.Organic functional groups Lucas reagent (1°, 2°, 3° alcohols)3 Iodoform reaction3 Identification of primary, secondary, tertiary, quarternary amines in the laboratory3
12.3.(2.7.19) Chromatographic methods of separation3