1、 2009.12 Syllabus of the IChO Copyleft CrB 1SYLLABUS 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 in
2、cluded 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
3、.1. The atom 原子结构1.1. Introduction1.1.1. Counting of nucleons 原子核序数 11.1.2. Isotopes 同位素 11.2. The hydrogen atom 1.2.1. Concept of energy levels 能级的概念 11.2.2. Shape of s-orbitals s轨道的形状 11.2.3. Shape and orientation of p-orbitals p轨道的形状和取向 11.2.4. Shape and orientation of d-orbitals d轨道的形状和取向 31.2.5
4、. Understanding the simplest Schrodinger equation 31.2.6. Square of the wave function and probability 波函数的平方和几率 31.2.7. Quantum numbers (n, l, ml) 31.3. Radioactivity 放射性1.3.1. Types of radioactivity 11.3.2. Radioactive decay 放射性衰变 11.3.3. Nuclear reactions 核反应 22. Chemical bonding 化学键2.1. VSEPR Sim
5、ple molecular structures with2.1.1. no more than four electron pairs about central atom 12.1.2. with central atom exceeding the “octet rule” 八隅律 32.2. Delocalization and resonance 离域和共振 32.3. Hybrid orbital theory 杂化轨道理论 32.4. Molecular orbital theory 分子轨道理论2.4.1. molecular orbital diagram (H2 molec
6、ule) 32.4.2. molecular orbital diagram (N2 and O2 molecules) 32009.12 Syllabus of the IChO Copyleft CrB 22.4.3. bond orders in O2, O2, O2+ 32.4.4. unpaired electrons and paramagnetism 未成对电子和顺磁性 33. Chemical calculations3.1.1. Balancing equations 13.1.2. Stoichiometric calculations 13.1.3. Mass and v
7、olume relations (including density) 13.1.4. Empirical formula 实验式 13.1.5. Avogadros number 13.1.6. Concentration calculations 浓度计算 14. Periodic trends 周期律4.1. Electron configuration 电子构型4.1.1. Pauli exclusion principle 14.1.2. Hunds Rule 14.1.3. Main group elements 14.1.4. Transition metal elements
8、14.1.5. Lanthanide and actinide metals 34.2. Electronegativity 电负性 14.3. Electron affinity 电子亲和能 24.4. First ionization energy 第一电离能 14.5. Atomic size 14.6. Ion size 14.7. Highest oxidation number 15. Inorganic Chemistry5.1. Introduction5.1.1. Trends in physical properties of elements (Main groups)5
9、.1.1.1. melting point 15.1.1.2. boiling point 15.1.1.3. metal character 15.1.1.4. magnetic properties 35.1.1.5. electrical conductivity 导电性 25.1.2. Oxidation number 15.1.3. Nomenclature5.1.3.1. main group compounds 15.1.3.2. transition metal compounds 15.1.3.3. simple metal complexes 35.2. Groups 1
10、and 2 一二族5.2.1. Trend in reactivity of (heavy elements more reactive) 15.2.2. Products of reaction with5.2.2.1. water 12009.12 Syllabus of the IChO Copyleft CrB 35.2.2.2. Halogens 卤素 15.2.2.3. oxygen 25.2.3. Basicity of oxides 氧化物的酸碱性 15.2.4. Properties of hydrides 氢化物的性质 35.2.5. Other compounds, pr
11、operties and oxidation states 35.3. Groups 13 18 and Hydrogen5.3.1. Binary molecular compounds of hydrogen 二元氢化物5.3.1.1. Formulae 15.3.1.2. Acid-base properties of CH4, NH3, H2O, H2S 15.3.1.3. Other properties 35.3.2. P block elements p区元素Group 13 (Boron group)5.3.2.1 The oxidation state of boron 硼
12、and aluminium 铝 in their oxides 氧化物 and chlorides 氯化物 is +315.3.2.2. The acid-base properties of aluminium oxide/hydroxide25.3.2.3. Reaction of boron(III) oxide with water 35.3.2.4. Reaction of boron(III) chloride with water 35.3.2.5. Other compounds, properties and oxidation states 35.3.3. Group 14
13、 (Carbon group)5.3.3.1. The oxidation state of Si in its chloride and oxide is +415.3.3.2. The +2 and +4 oxidation states of carbon, tin 锡 and lead 铅, the acid-base and redox 氧化-还原properties of the oxides and chlorides25.3.3.3. Other compounds, properties and oxidation states 35.3.4. Group 15 (Nitro
14、gen group)5.3.4.1. Phosphorus 磷 (+5) oxide and chloride, and their reaction with water25.3.4.2. Phosphorus(+3) oxide and chloride, and their reaction with water25.3.4.3. Oxides of nitrogena. Reaction of NO to form NO2 1b. Dimerization 二聚 of NO2 1c. Reaction of NO2 with water 15.3.4.4. Redox properti
15、es ofa. HNO3 and nitrates 硝酸盐 1b. HNO2 and NH2NH2 35.3.4.5. Bi(+5) and Bi(+3) 35.3.4.6. Other compounds, properties and oxidation states 35.3.5. Group 16 (Oxygen group)2009.12 Syllabus of the IChO Copyleft CrB 45.3.5.1. The +4 and +6 oxidation states of sulfur, reaction of their oxides with water, p
16、roperties of their acids15.3.5.2. Reaction of thiosulfate 硫代硫酸根 anion with I2 35.3.5.3. Other compounds, properties and oxidation states 35.3.6. Group 17 (Halogens)5.3.6.1. Reactivity and oxidant 氧化 strength decreases from F2 to I215.3.6.2. Acid-base properties of the hydrogen halides 卤化氢 15.3.6.3.
17、The oxidation state of fluorine 氟 in its compounds is 115.3.6.4. The 1, +1, +3, +5, +7 oxidation states of chlorine 15.3.6.5. Mononuclear 单核的 oxoanions of chlorine 25.3.6.6. Reactions of halogens with water 35.3.6.7. Reaction of Cl2O and Cl2O7 with water 35.3.6.8. Other compounds, properties and oxi
18、dation states 35.3.7. 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 solution 水溶液中的颜色
19、 25.4.3. Insolubility 不溶性 of Ag, Hg and Cu in HCl 25.4.4. M2+ arising by dissolution of the other metals in HCl 25.4.5. Cr(OH)3 and Zn(OH)2 are amphoteric 两性的 and the other +2oxides/hydroxides 氧化物和氢氧化物 of the metals listed above are basic25.4.6. MnO4 and Cr2O72 are strong oxidants in acid solution 1
20、5.4.7. pH dependence of products of MnO4 acting as oxidant 25.4.8. Interconversion between CrO42 and Cr2O72 35.4.9. Other compounds, properties and oxidation states 35.5. Lanthanides and actinides 35.6. Coordination配位 chemistry including stereochemistry 立体化学5.6.1. Definition of coordination number 1
21、5.6.2. Writing equations for complexation reactions given all formulae15.6.3. Formulae of common complex ions5.6.3.1. Ag(NH3)2+ 15.6.3.2. Ag(S2O3)23 35.6.3.3. FeSCN2+ 35.6.3.4. Cu(NH3)42+ 15.6.3.5. Other complex ions 32009.12 Syllabus of the IChO Copyleft CrB 55.6.4. (6.5) Ligand field theory (eg an
22、d t2g terms, high and low spin 自旋 ) 35.6.5. Stereochemistry 立体化学5.6.5.1. (6.7) cis and trans 35.6.5.2. Enantiomers 对映体 35.7. Selected industrial processes5.7.1. Preparation of H2SO4 15.7.2. Preparation of NH3 15.7.3. Preparation of Na2CO3 25.7.4. Preparation of Cl2 and NaOH 25.7.5. Preparation of HN
23、O3 26. Physical chemistry6.1. Gases6.1.1. Ideal gas law 理想气体定律 16.1.2. van der Waals gas law 范德华气体定律 36.1.3. definition of partial pressure 分压的定义 26.1.4. Daltons Law 道尔顿定律 36.2. Thermodynamics 热力学6.2.1. First Law 热力学第一定律6.2.1.1. Concept of system and surroundings 体系和环境 26.2.1.2. Energy, heat and wor
24、k 26.2.2. Enthalpy 焓6.2.2.1. Relationship between internal energy and enthalpy 内能和焓的关系36.2.2.2. Definition of heat capacity 热容的定义 26.2.2.3. Difference between Cp and Cv (ideal gas only) 36.2.2.4. Enthalpy is a state property (Hesss Law) 26.2.2.5. Born-Haber cycle for ionic compounds 离子化合物 36.2.2.6.
25、Use of standard formation enthalpies 26.2.2.7. Enthalpies of solution and salvation 溶解/ 稀释焓 36.2.2.8. Bond enthalpies (definition and use) 键焓 26.2.3. Second Law (Entropy and Free Energy)6.2.3.1. Entropy definition (dq / T) 熵的定义 36.2.3.2. Entropy and disorder 熵和混乱度 36.2.3.3. Entropy definition (S = k
26、 ln W) 熵的定义 36.2.3.4. Gibbs energy definition (G = H TS) 36.2.3.5. Using G to predict direction of natural 自发 change 36.2.3.6. Relationship between G and equilibrium constant K 36.3. Equilibrium 平衡6.3.1. Acid-base 酸碱平衡6.3.1.1. Arrhenius definitions of acids and bases 16.3.1.2. Bronsted-Lowry definit
27、ions 12009.12 Syllabus of the IChO Copyleft CrB 66.3.1.3. Conjugate acids and bases 16.3.1.4. pH definition 16.3.1.5. Kw definition 16.3.1.6. Ka and Kb as a measure of acid and base strength 16.3.1.7. Acidity or basicity of ions 16.3.1.8. Calculation of pH from pKa(weak acid) 16.3.1.9. Calculation o
28、f pH of a simple buffer solution 26.3.2. Gas phase 气相6.3.2.1. Equilibrium constant in partial pressures 36.3.2.2. Relating 换算 Kp and Kc 36.3.3. Solubility 溶度积6.3.3.1. Solubility constant (product) definition (Ksp) 26.3.3.2. Calculation of solubility in water from Ksp 26.3.4. Compleximetric 络合6.3.4.1
29、. Complex formation constant (definition) 36.3.4.2. Problems involving compleximetric equilibria 36.3.4.3. Lewis acids and bases 36.3.4.4. Hard and soft Lewis acids and bases 36.3.5. Phase 相6.3.5.1. Temperature dependence of vapour pressure 蒸汽压和温度 36.3.5.2. Clausius-Clapeyron equation 36.3.5.3. Sing
30、le component phase diagrams 单组分相图a. triple point 三相点 3b. critical point 临界点 36.3.5.4. liquid-vapour system 液气体系a. ideal and nonideal systems 3b. diagram 3c. use in fractional distillation 分馏中的应用 36.3.5.5. Henrys Law 36.3.5.6. Raoults Law 36.3.5.7. Deviation 偏离 from Raoults Law 36.3.5.8. Boiling poin
31、t elevation 沸点升高 36.3.5.9. Freezing point depression 冰点降低 36.3.5.10. Osmotic pressure 渗透压 36.3.5.11. Partition coefficient 分配系数 36.3.5.12. Solvent extraction 萃取 36.3.6. Multiple6.3.6.1. Calculation of pH for multiprotic 多元的 acids 36.3.6.2. Calculation of pH for weak acid mixtures 36.4. Electrochemis
32、try 电化学6.4.1. Electromotive force (definition) 电动势 16.4.2. First kind electrodes 第一类电极 12009.12 Syllabus of the IChO Copyleft CrB 76.4.3. Standard electrode potential 标准电极电势 16.4.4. Nernst equation 36.4.5. Second kind electrodes 36.4.6. Relationship between G and electromotive force 37. Chemical kin
33、etics (Homogeneous 均相reactions)7.1. Introduction7.1.1. Factors affecting reaction rate 17.1.2. Reaction coordinates 反应历程 and the basic idea of a transition state 过渡态17.2. Rate law7.2.1. Differential rate law 27.2.2. Concept of reaction order 27.2.3. Rate constant definition 27.2.4. First order react
34、ions7.2.4.1. Dependence of concentration on time 37.2.4.2. Concept of half life 37.2.4.3. Relationship between half life and rate constant 37.2.4.4. Calculation of first order rate constant froma. differential rate law 3b. integrated rate law 37.2.4.5. Rate constant for second and third order reacti
35、ons 37.3. Reaction mechanisms 反应机制7.3.1. Concept of molecularity 分子数的概念 37.3.2. Rate-determining step 速控步骤 37.3.3. Basic concepts of collision theory 碰撞理论的基本概念 37.3.4. Opposing parallel and consecutive reactions 平行反应和连续反应 37.3.5. Arrheniuss law 37.3.5.1. Definition of activation energy 37.3.5.2. Cal
36、culation of activation energy 38. Spectroscopy 光谱学8.1. UV/visible 紫外可见8.1.1. Identification of aromatic compound 芳香族化合物的鉴定 38.1.2. Identification of chromophore 生色基的鉴定 38.1.3. Dyes: colour vs structure 染料颜色和结构的关系 38.1.4. Beers Law 比尔定律 38.2. Infrared 红外8.2.1. Interpretation using a table of frequenc
37、ies 38.2.2. Recognition of hydrogen bonds 氢键的识别 38.3. x-Ray8.3.1. Braggs Law 布拉格方程 32009.12 Syllabus of the IChO Copyleft CrB 88.3.2. Concept of8.3.2.1. coordination number 配位数 38.3.2.2. unit cell 晶胞 38.3.3. Solid structures8.3.3.1. NaCl 38.3.3.2. CsCl 38.3.3.3. metals 38.4. NMR8.4.1. General Concep
38、ts8.4.1.1. chemical shift 38.4.1.2. spin-spin coupling and coupling constants 耦合&耦合常数 38.4.1.3. Integration 综合 38.4.2. Interpretation of a simple 1H spectrum (like ethanol) 一级谱的识别 38.4.3. Identification of o- and p-disubstituted benzene 二取代苯 38.4.4. Interpretation of simple spectra of 13C (proton de
39、coupled质子去耦) and other 1/2 spin nuclei 38.5. Mass spectrometry8.5.1.1. Recognition of molecular ion 分子离子 38.5.1.2. Recognition of fragments 碎片 with the help of a table 38.5.1.3. Recognition of typical isotope distribution 同位素丰度 39. Organic Chemistry9.1. Introduction9.1.1. (3.1.1) Alkane naming (IUPA
40、C) 19.1.2. Trends in boiling points of9.1.2.1. (3.1.3) alkanes with structure 19.1.2.2. (3.7.1) alcohols vs ethers due to hydrogen-bonding 19.1.3. (3.3.1, 3.4.1) Geometry at singly, doubly, and triply bonded carbon19.1.4. Identification of common functional groups 19.1.5. Isomerism of alkenes9.1.5.1
41、. cis-trans 19.1.5.2. E/Z 39.1.6. Enantiomers9.1.6.1. Optical activity 29.1.6.2. R/S nomenclature 39.2. Reactivity9.2.1. Alkanes9.2.1.1. reaction with halogensa. products 1b. free radical mechanism (initiation, termination) 29.2.1.2. Cycloalkanes2009.12 Syllabus of the IChO Copyleft CrB 9a. names 2b
42、. Strain in small rings 小环张力学说 3c. chair/boat conformations of cyclohexane 39.2.2. Alkenes9.2.2.1. Products from Br2, HBr and H2O/H+ 19.2.2.2. Markownikoffs rule 29.2.2.3. Mechanism involving carbocation intermediates 碳正离子中间体机理39.2.2.4. Relative stability of carbocations 碳正离子的相对稳定性 39.2.2.5. 1,4 add
43、ition to dienes 双烯 39.2.3. Alkynes9.2.3.1. Acidity relative to alkenes 39.2.3.2. Differences in chemical properties from alkenes 29.2.4. Benzene9.2.4.1. formula 19.2.4.2. stabilization by resonance 19.2.4.3. electrophilic substitution (nitration, halogenation) 亲电取代，硝化，卤化a. directing effect of first
44、substituent 3b. effect of first substituent on reactivity 定位效应 3c. explanation of substituent effects 定位效应的解释 39.2.5. Halogen compounds 卤代烃9.2.5.1. Nomenclature of monofunctional 19.2.5.2. Substitution reactionsa. giving alcohols 3b. in which halogen is exchanged 3c. reactivityi. primary vs secondar
45、y vs tertiary 3ii. aliphatic vs aromatic 3d. SN1 and SN2 mechanisms 39.2.5.3. Elimination reactions 消去反应 29.2.5.4. Competition of elimination and substitution 竞争 29.2.6. Alcohols9.2.6.1. Nomenclature of monofunctional 19.2.6.2. Comparison of acidity of alcohols and phenols 酚类 29.2.6.3. Dehydration t
46、o alkenes 19.2.6.4. Esters with inorganic acid 29.2.6.5. Oxidation reactions 19.2.7. Aldehydes and ketones 醛和酮9.2.7.1. Nomenclature of monofunctional 19.2.7.2. Oxidation of aldehydes 19.2.7.3. Reduction to alcohols (LiAlH4, NaBH4) 32009.12 Syllabus of the IChO Copyleft CrB 109.2.7.4. Keto/enol tauto
47、merism 酮式-烯醇互变 39.2.7.5. Nucleophilic addition reactions with 亲核反应a. HCN 3b. RNH2 (R = alkyl, HO, NH2) 3c. enolate anions (aldol condensation) 烯醇阴离子，羟醛缩合3d. alcohols to form acetals/ketals 缩醛酮 3e. Grignard reagents 39.2.8. Carboxylic acids and their derivatives9.2.8.1. Nomenclature of carboxylic aci
48、ds and their derivatives (esters, acid halides, amides)29.2.8.2. Acidity strength related to inductive effects 39.2.8.3. Preparation of carboxylic acids by hydrolysis ofa. esters (including soaps) 1b. amides 2c. nitriles 39.2.8.4. Reaction of carboxylic acidsa. with alcohols to form esters 1b. to fo
49、rm acid chlorides 3c. to form anhydrides 39.2.8.5. Reaction of acid chlorides to form amides 39.2.8.6. Mechanism of esterification 39.2.8.7. Multifunctional acids (hydroxyacids, ketoacids) 39.2.8.8. Polycarboxylic acids 39.2.9. Amines9.2.9.1. Nomenclaturea. simple amines 1b. recognition of primary, secondary, tertiary 19.2.9.2. Basicitya. As a property of an amine 1b. Comparison of basicity of aliphatic and aromatic 3c. Comparison of basicity of amines and amides 3d. Preparation of aminesi. from halides 3ii. from aromatic n
