IChO(国际化学奥林匹克竞赛)考试大纲[1].doc

152009.12 Syllabus of the IChOCopyleft CrB SYLLABUS OF THE INTERNATIONAL CHEMISTRY OLYMPIADPart I Theoretical partLevel 1: These topics are included in the overwhelming majority of secondary school chemistry programs and need not 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. The atom1.1.Introduction1.1.1.Counting of nucleons11.1.2.Isotopes11.2.The hydrogen atom1.2.1.Concept of energy levels11.2.2.Shape of s-orbitals11.2.3.Shape and orientation of p-orbitals11.2.4.Shape and orientation of d-orbitals31.2.5.Understanding the simplest Schrodinger equation31.2.6.Square of the wave function and probability31.2.7.Quantum numbers (n, l, ml)31.3.Radioactivity1.3.1.Types of radioactivity11.3.2.Radioactive decay11.3.3.Nuclear reactions22. Chemical bonding2.1.VSEPR Simple molecular structures with2.1.1.no more than four electron pairs about central atom12.1.2.with central atom exceeding the “octet rule”32.2.Delocalization and resonance32.3.Hybrid orbital theory32.4.Molecular orbital theory2.4.1.molecular orbital diagram (H2 molecule)32.4.2.molecular orbital diagram (N2 and O2 molecules)32.4.3.bond orders in O2, O2, O2+32.4.4.unpaired electrons and paramagnetism33. Chemical calculations3.1.1.Balancing equations13.1.2.Stoichiometric calculations13.1.3.Mass and volume relations (including density)13.1.4.Empirical formula13.1.5.Avogadros number13.1.6.Concentration calculations14. Periodic trends4.1.Electron configuration4.1.1.Pauli exclusion principle14.1.2.Hunds Rule14.1.3.Main group elements14.1.4.Transition metal elements14.1.5.Lanthanide and actinide metals34.2.Electronegativity14.3.Electron affinity24.4.First ionization energy14.5.Atomic size14.6.Ion size14.7.Highest oxidation number15. Inorganic Chemistry5.1.Introduction5.1.1.Trends in physical properties of elements (Main groups).melting point.boiling point.metal character.magnetic properties.electrical conductivity25.1.2.Oxidation number15.1.3.Nomenclature.main group compounds.transition metal compounds.simple metal complexes35.2.Groups 1 and 25.2.1.Trend in reactivity of (heavy elements more reactive)15.2.2.Products of reaction with.water.halogens.oxygen25.2.3.Basicity of oxides15.2.4.Properties of hydrides35.2.5.Other compounds, properties and oxidation states35.3.Groups 13 18 and Hydrogen5.3.1.Binary molecular compounds of hydrogen.Formulae.Acid-base properties of CH4, NH3, H2O, H2S.Other properties35.3.2.P block elementsGroup 13 (Boron group)The oxidation state of boron and aluminium in their oxides and chlorides is +3.The acid-base properties of aluminium oxide/hydroxide.Reaction of boron(III) oxide with water.Reaction of boron(III) chloride with water.Other compounds, properties and oxidation states35.3.3.Group 14 (Carbon group).The oxidation state of Si in its chloride and oxide is +4.The +2 and +4 oxidation states of carbon, tin and lead, the acid-base and redox properties of the oxides and chlorides.Other compounds, properties and oxidation states35.3.4.Group 15 (Nitrogen group).Phosphorus(+5) oxide and chloride, and their reaction with water.Phosphorus(+3) oxide and chloride, and their reaction with water.Oxides of nitrogena. Reaction of NO to form NO21b. Dimerization of NO21c. Reaction of NO2 with water.Redox properties ofa. HNO3 and nitrates1b. HNO2 and NH2NH.Bi(+5) and Bi(+3).Other compounds, properties and oxidation states35.3.5.Group 16 (Oxygen group).The +4 and +6 oxidation states of sulfur, reaction of their oxides with water, properties of their acids.Reaction of thiosulfate anion with I.Other compounds, properties and oxidation states35.3.6.Group 17 (Halogens).Reactivity and oxidant strength decreases from F2 to I.Acid-base properties of the hydrogen halides.The oxidation state of fluorine in its compounds is .The 1, +1, +3, +5, +7 oxidation states of chlorine.Mononuclear oxoanions of chlorine.Reactions of halogens with water.Reaction of Cl2O and Cl2O7 with water.Other compounds, properties and oxidation states35.3.7.Group 18 (Rare gases)35.4. Transition elements5.4.1.Common oxidation states of common transition metals: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)15.4.2.Colours of ions listed above in aqueous solution25.4.3.Insolubility of Ag, Hg and Cu in HCl25.4.4.M2+ arising by dissolution of the other metals in HCl25.4.5.Cr(OH)3 and Zn(OH)2 are amphoteric and the other +2oxides/hydroxides of the metals listed above are basic25.4.6.MnO4 and Cr2O72 are strong oxidants in acid solution15.4.7.pH dependence of products of MnO4 acting as oxidant25.4.8.Interconversion between CrO42 and Cr2O7235.4.9.Other compounds, properties and oxidation states35.5.Lanthanides and actinides35.6.Coordination chemistry including stereochemistry5.6.1.Definition of coordination number15.6.2.Writing equations for complexation reactions given all formulae15.6.3.Formulae of common complex ions.Ag(NH3)2+.Ag(S2O3)23.FeSCN2+.Cu(NH3)42+.Other complex ions35.6.4.(6.5) Ligand field theory (eg and t2g terms, high and low spin)35.6.5.Stereochemistry.(6.7) cis and trans.enantiomers35.7.Selected industrial processes5.7.1.Preparation of H2SO415.7.2.Preparation of NH315.7.3.Preparation of Na2CO325.7.4.Preparation of Cl2 and NaOH25.7.5.Preparation of HNO326. Physical chemistry6.1.Gases6.1.1.Ideal gas law16.1.2.van der Waals gas law36.1.3.definition of partial pressure26.1.4.Daltons Law36.2. Thermodynamics6.2.1.First Law.Concept of system and surroundings.Energy, heat and work26.2.2.Enthalpy.Relationship between internal energy and enthalpy.Definition of heat capacity.Difference between Cp and Cv (ideal gas only).Enthalpy is a state property (Hesss Law).Born-Haber cycle for ionic compounds.Use of standard formation enthalpies.Enthalpies of solution and solvation.Bond enthalpies (definition and use)26.2.3.Second Law (Entropy and Free Energy).Entropy definition (dq / T).Entropy and disorder.Entropy definition (S = k ln W).Gibbs energy definition (DG = DH TDS).Using DG to predict direction of natural change.Relationship between DG and equilibrium constant K36.3.Equilibrium6.3.1.Acid-base.Arrhenius definitions of acids and bases.Bronsted-Lowry definitions.Conjugate acids and bases.pH definition.Kw definition.Ka and Kb as a measure of acid and base strength.Acidity or basicity of ions.Calculation of pH from pKa(weak acid).Calculation of pH of a simple buffer solution26.3.2.Gas phase.Equilibrium constant in partial pressures.Relating Kp and Kc36.3.3.Solubility.Solubility constant (product) definition (Ksp).Calculation of solubility in water from Ksp26.3.4.Compleximetric.Complex formation constant (definition).Problems involving compleximetric equilibria.Lewis acids and bases.Hard and soft Lewis acids and bases36.3.5.Phase.Temperature dependence of vapour pressure.Clausius-Clapeyron equation.Single component phase diagramsa. triple point3b. critical point.liquid-vapour systema. ideal and nonideal systems3b. diagram3c. use in fractional distillation.Henrys Law.Raoults Law.Deviation from Raoults Law.Boiling point elevation.Freezing point depression0.Osmotic pressure1.Partition coefficient2.Solvent extraction36.3.6.Multiple.Calculation of pH for multiprotic acids.Calculation of pH for weak acid mixtures36.4.Electrochemistry6.4.1.Electromotive force (definition)16.4.2.First kind electrodes16.4.3.Standard electrode potential16.4.4.Nernst equation36.4.5.Second kind electrodes36.4.6.Relationship between DG and electromotive force37. Chemical kinetics (Homogeneous reactions)7.1.Introduction7.1.1.Factors affecting reaction rate17.1.2.Reaction coordinates and the basic idea of a transition state17.2.Rate law7.2.1.Differential rate law27.2.2.Concept of reaction order27.2.3.Rate constant definition27.2.4.First order reactions.Dependence of concentration on time.Concept of half life.Relationship between half life and rate constant.Calculation of first order rate constant froma. differential rate law3b. integrated rate law.Rate constant for second and third order reactions37.3.Reaction mechanisms7.3.1.Concept of molecularity37.3.2.Rate-determining step37.3.3.Basic concepts of collision theory37.3.4.Opposing parallel and consecutive reactions37.3.5.Arrheniuss law.Definition of activation energy.Calculation of activation energy38. Spectroscopy8.1.UV/visible8.1.1.Identification of aromatic compound38.1.2.Identification of chromophore38.1.3.Dyes: colour vs structure38.1.4.Beers Law38.2.Infrared8.2.1.Interpretation using a table of frequencies38.2.2.Recognition of hydrogen bonds38.3.x-Ray8.3.1.Braggs Law38.3.2.Concept of.coordination number.unit cell38.3.3.Solid structures.NaCl.CsCl.metals38.4.NMR8.4.1.General Concepts.chemical shift.spin-spin coupling and coupling egration38.4.2.Interpretation of a simple 1H spectrum (like ethanol)38.4.3.Identification of o- and p-disubstituted benzene38.4.4.Interpretation of simple spectra of 13C (proton decoupled) and other 1/2 spin nuclei38.5.Mass spectrometry.Recognition of molecular ion.Recognition of fragments with the help of a table.Recognition of typical isotope distribution39. Organic Chemistry9.1.Introduction9.1.1.(3.1.1) Alkane naming (IUPAC)19.1.2.Trends in boiling points of.(3.1.3) alkanes with structure.(3.7.1) alcohols vs ethers due to hydrogen-bonding19.1.3.(3.3.1, 3.4.1) Geometry at singly, doubly, and triply bonded carbon19.1.4.Identification of common functional groups19.1.5.Isomerism of alkenes.cis-trans.E/Z39.1.6.Enantiomers.Optical activity.R/S nomenclature39.2.Reactivity9.2.1.Alkanes.reaction with halogensa. products1b. free radical mechanism (initiation, termination).Cycloalkanesa. names2b. Strain in small rings3c. chair/boat conformations of cyclohexane39.2.2.Alkenes.Products from Br2, HBr and H2O/H+.Markownikoffs rule.Mechanism involving carbocation intermediates.Relative stability of carbocations.1,4 addition to dienes39.2.3.Alkynes.Acidity relative to alkenes.Differences in chemical properties from alkenes29.2.4.Benzene.formula.stabilization by resonance.electrophilic substitution (nitration, halogenation)a. directing effect of first substituent3b. effect of first substituent on reactivity3c. explanation of substituent effects39.2.5.Halogen compounds.Nomenclature of monofunctional.Substitution reactionsa. giving alcohols3b. in which halogen is exchanged3c. reactivityi. primary vs secondary vs tertiary3ii. aliphatic vs aromatic3d. SN1 and SN2 mechanisms.Elimination reactions.Competition of elimination and substitution29.2.6.Alcohols.Nomenclature of monofunctional.Comparison of acidity of alcohols and phenols.Dehydration to alkenes.Esters with inorganic acid.Oxidation reactions19.2.7.Aldehydes and ketones.Nomenclature of monofunctional.Oxidation of aldehydes.Reduction to alcohols (LiAlH4, NaBH4).Keto/enol tautomerism.Nucleophilic addition reactions witha. HCN3b. RNH2 (R = alkyl, HO, NH2)3c. enolate anions (aldol condensation)3d. alcohols to form acetals/ketals3e. Grignard reagents39.2.8.Carboxylic acids and their derivatives.Nomenclature of carboxylic acids and their derivatives (esters, acid halides, amides).Acidity strength related to inductive effects.Preparation of carboxylic acids by hydrolysis ofa. esters (including soaps)1b. amides2c. nitriles.Reaction of carboxylic acidsa. with alcohols to form esters1b. to form acid chlorides3c. to form anhydrides.Reaction of acid chlorides to form amides.Mechanism of esterification.Multifunctional acids (hydroxyacids, ketoacids).Polycarboxylic acids39.2.9.Amines.Nomenclaturea. simple amines1b. recognition of primary, secondary, tertiary.Basicitya. As a property of an amine1b. Comparison of basicity of aliphatic and aromatic3c. Comparison of basicity of amines and amides3d. Preparation of aminesi. from halides3ii. from aromatic nitro compounds3iii. from amides (by hydrolysis).Diazotizationa. of aliphatic amines3b. of aromatic amines310. Polymers10.1.Synthetic10.1.1.Addition polymers.polystyrene.polyethene.chain mechanism of formation210.1.2.Condensation polymers.polyesters.polyamides210.1.3.Silicones310.1.4.Concept of cross-linking and its affect on properties310.2.Natural10.2.1.Silicates310.2.2.Rubber311. Biochemistry11.1.Carbohydrates11.1.1.Glucose and fructose.chain formulae.Fischer projections.Haworth formulae311.1.2.Difference between starch and cellulose211.1.3.Difference between a- and b- D glucose211.2.Fats11.2.1.Structure of fats in relationship to properties211.2.2.Formula of glycerol111.3.Nitrogen-containing Compounds of Biological Importance11.3.1.Amino acids.Ionic structure.Isoelectric point3.20 amino acids (classification with structures provided).Separation by electrophoresis3.The peptide linkage111.3.2.Proteins.Primary structure.S-S- bridges3.Sequence analysis3.Secondary structure3.Details of a-helix str