Chemistry Olympiad Advanced Class Syllabus
Comprehensive Review Topics
Topic 1: Atomic structure and periodicity
1.1 The introduction to wave mechanics
--The wave-nature of electrons
--The uncertainty principle
--The Schrödinger wave equation
1.2 Atomic Orbitals
--The quantum numbers n, l, and ml
--The radial part of the wavefunction, R(r)
--The angular part of the wavefunction, A(θ, Ф)
--Radial and Angular Nodes
--Orbital energies in a hydrogen-like species
--The spin quantum number and the magnetic spin quantum number
--The Bohr model
1.3 Many-Electron Atoms
--Ground State electronic Configuration: Experimental Data
--Penetration and Shielding
1.4 The Periodic Table
1.5 The Aufbau Principle
--Valene and core electrons
--Diagrammatic representations of electronic configurations
1.6 Periodic Trends in Atomic Properties
--Ionization Energy
--Electron Affinity
--Electronegativity
--Polarizabilities
--Inert-pair effect
--Diagonal Relationship
--Slater Rules
1.7 Atomic Properties and Chemical Reactivity
--Trends in Metallic Behavior
--Relative Tendency to Lose or Gain Electrons
--Redox Behavior of the Main-Group Elements
--Acid-Base Behavior of Oxides
--Properties of Monatomic Ions
--Electron Configurations of Transition Metal Ions
--Magnetic Properties of Transition Metal Ions
1.8 Challenge and Integrative Problems
1.9 Olympiad Exam
Topic 2: Molecular structure and bonding
2.1 Bonding models
--Lewis structures
--Resonance structures
--Formal charges and applications
2.2 Homonuclear diatomic molecules: valance bond (VB) theory
--VB model of bonding in H2
--VB model of bonding in F2, O2 and N2
2.3 Homonuclear diatomic molecules: Molecular orbital (MO) theory
--Bond order
--Magnetic properties
2.4 The Octet Rule and Isoelectronic species
--The octet rule: first row p–block elements
--Isoelectronic species
--The octet rule: heavier p–block elements
2.5 Dipole Moments
--Polar diatomic molecules
--Molecular dipole moments
2.6 Molecular Shape and VSEPR model
--VSEPR model
--Structures derived from a trigonal bipyramid
--Limitations of the VSEPR model
2.7 Molecular Shape: Stereoisomerism
--Square planar species
--Octahedral species
--Trigonal bipyramidal species
--High coordination numbers
--Double bonds
2.8 Valance Bond Theory: Hybridization of Atomic Orbitals
--sp Hybridization: linear species
--sp2 Hybridization: trigonal planar and related species
--sp3 Hybridization: tetrahedral and related species
--Other hybridization
--Limitations to the concept of hybridization
2.9 Electronegativity and Bond Angles
2.10 Challenge and Integrative Problems
2.11 Olympiad Exam
Topic 3: States of Matter and Solutions
3.1 The Kinetic Molecular Theory of Gases
3.2 Effusion and Diffusion of Gases
3.3 Chemistry in the Atmosphere
3.4 A Kinetic-Molecular View of the Three States
3.5 Intermolecular Forces
--Hydrogen bond
--Ion-dipole forces
--Dipole-dipole forces
--Polarizability and induced dipole forces
--Dispersion (London) forces
--Biological Macromolecules
3.6 Structures and Types of Solids
--Packing of spheres
--Packing efficiency
--Determining atomic radius or density of solids
--Bragg equation
3.7 Structure and Bonding in Metals
--Molecular orbital band theory
--Conductors and semiconductors
--Doped semiconductors
3.8 Vapor Pressure and Changes of State
--The Clausius-Clapeyron equation
--Ionic liquids
3.9 Phase Diagrams
--Relationship between density and slope
3.10 The Energies of Solution Formation
3.11 Vapor Pressures of Solutions
--Binary liquid mixtures
--Distillation
--Azeotropes
3.12 Colloids
3.13 Challenge problems
3.14 Olympiad Exam
Topic 4: Chemical Kinetics
4.1 Concentrations and Reaction Rates
--Average rates
--Instantaneous rates
--Initial reactions rates
4.2 Unique Average reaction Rate
4.3 Determining the Rate Law
4.4 The Integrated Rate Law
--Radioactive decay rates
4.5 Reaction Mechanism
--Rate laws for elements reactions
--Two approaches to reaction mechanism
--Chain reactions
4.6 Steady State Kinetics
4.7 A Model for Chemical Kinetics
--Arrhenius equation
4.8 Kinetics and Function of Biological Catalysts
4.9 Challenge problems
4.10 Olympiad Exam
Topic 5: Chemical Equilibria
5.1 The Equilibrium State and the Equilibrium Constant
--Relation between Kc and Kp
5.2 The Reaction Quotient
5.3 Comparing Q and K to determine direction
5.4 How to Solve Equilibrium Problems
5.5 Le Châtelier's Principle
5.6 Catalysts, Chemical Kinetics and Equilibrium
5.7 Equilibria Involving the Solubility Product
--Common ion effect
--Effect of pH on solubility
--Predict the precipitation
--Selective precipitation
5.8 Equilibria involving the complex Ions
5.9 Equilibria Involving the Solubility Product and the Complex Ions
5.10 Challenge problems
5.11 Olympiad Exam
Topic 6: Acids and Bases
6.1 Acids and Bases
--Arrhenius acid-base and neutralization
--BrФnsted-Lowry acid-base pair
--Lewis acid-base pair
6.2 Calculating the pH of Acid Solutions
--Strong acids
--Very diluted strong acids
--Weak acids
--Mixture of strong acid and weak acid
--Mixture of two weak acids
--Polyprotic acids
--Percent dissociation
6.3 Bases
6.4 Acid-Base Properties of Salts
--Conjugated seesaw
--Salts That Produce Neutral Solutions
--Salts That Produce Basic Solutions
--Base Strength in Aqueous Solutions
--Salts That Produce Acidic Solutions
6.5 Calculate the pH of a Salt for Weak Acid and Weak Base
6.6 Generalizing the BrΦnsted-Lowry Concept: The Leveling effect
6.7 Calculate the pH of Salts of Polyprotic Acid
6.8 Composition and pH
6.9 Acid-Base Properties of Oxides
6.10 Challenge Problems and Olympiad Exam
Topic 7: Applications of Aqueous Equilibria
7.1 Buffered Solutions
--Compositions of buffered solution
--Buffering: How Does It Work
--Buffering Capacity
7.2 Stoichiometry of Polyprotic Acid Titrations
7.3 Quantifying Redox Reactions by Titration
7.4 Back Titration
7.5 Challenge problems
7.6 Olympiad Exam
Topic 8: Thermodynamics: The First Law
8.1 Expansion Work
8.2 Energy and Enthalpy
8.3 The Thermodynamic Standard State
8.4 Enthalpies of Physical and Chemical Change
8.5 Calorimetry and Heat Capacity
8.6 Calculating Enthalpy Change --- Hess's Law
8.7 Standard Enthalpies of Formation
8.8 The Born-Haber Cycle
8.9 Bond Enthalpies
8.10 Bond Strengths and the Heat Released from Fuels and Foods
8.11 Challenge Problems
8.12 Olympiad Exam
Topic 9: Thermodynamics: The Second and Third Laws
9.1 Spontaneous Processes and Entropy
--Predicting change in entropy
--Quantitative definition of entropy
9.2 Changes in Entropy
--Thermal disorder
--Positional disorder
9.3 Entropy Changes Accompanying Changes in Physical Stats
9.4 Standard Molar Entropies
--The third law of thermodynamics
9.5 The Surroundings
9.6 The Overall change in Entropy
9.7 Equilibrium
9.8 Free Energy
--Estimate the minimum temperature for reactions
--The thermodynamic tendency
--The thermokinetic tendency 9.9 Free Energy and Chemical Reactions
9.10 The Dependence of Free Energy on Pressure
9.11 Free Energy and Equilibrium
--Van’t Hoff equation
9.12 Challenge Problems
9.13 Olympiad Exam
Topic 10: Electrochemistry
10.1 Introduction
--Galvanic Cells
--Standard Reduction Potentials 10.2 Standard Reduction potentials, ξ°, and relationships between ξ°, ΔG° and K
--Half-cells and galvanic cells
--Defining and using standard reduction potentials, ξ°
--Dependence of reduction potentials on cell conditions
10.3 The effect of complex formation or precipitation on Mz+/M reduction potential
--Half-cells involving silver halides
--Modifying the relative stabilities of different oxidation states of a metal
10.4 Latimer diagrams
10.5 Disproportionation reactions
10.6 The relationships between standard reduction potentials and some other quantities
--Factors influencing the magnitudes of standard reduction potentials
--Values of ΔGf° for aqueous ions
10.7 Fuel cells
10.8 Electrolysis
10.9 Corrosion
10.10 Challenge Problems
10.11 Olympiad Exam
Advanced Chemistry - (continued from Chapter 18 of Level 1)
Chapter 19 - The Representative Elements: Groups 1A through 4A
19.1 A Survey of the Representative Elements
--Atomic Properties
--Bonding Trends
--First-Row Anomaly
--Abundance of Elements
--Preparations of Elements
19.2 The Group 1A Elements
--The Most Negative °ξ of Li
--Ink-Blue Metal-Ammonia Solutions
--Compounds of Li, Na and K
19.3 Hydrogen
--Preparations
--Intrahydrogen Bonding
--Three Classes of Hydrides
19.4 The Group 2A Elements
--Diagonal Relationship
--Coordinate Bonding
--BeCl2 Covalent Bonding
--AlCl3 Bridge Bonding
--Cation-Exchange Resin
19.5 The Group 3A Elements
--Multiple Oxidation States and Inert-Pair Effect
--Amphoteric Oxide
--Hall Process
--Boranes and Three-Center Bonds
19.6 The Group 4A Elements
--Alltropism: Graphite, Diamonds and Buckminsterfullerence
--Carbon Chemistry
--Silicon Chemistry
--The Bonding of Carbonyl Complexes
19.7 Challenge Problems
Chapter 20 - The Representative Elements: Groups 5A through 8
20.1 The Group 5A Elements
--Thermal Stability of Hydrides
--Three, Five or Six Covalent Bonds
20.2 The Chemistry of Nitrogen
--Nitrogen Hydrides
--Nitrogen Oxides
--Lewis Structures and Molecular Orbitals
--Oxyacids of Nitrogen
20.3 The Chemistry of Phosphorus
--Phosphorus Oxides and Oxyacids
--Phosphorus in Fertilizers
--Phosphorus Halides
20.4 The Group 6A Elements
--SP3 hybridization and Unhybridized p orbitals
20.5 The Chemistry of Oxygen
--Allotropic O2 and O3
--Structure of H2O2
20.6 The Chemistry of Sulfur
--Sulfur Oxides
--Oxyacids of Sulfur
--Other Compounds of Sulfur
20.7 The Group 7A Elements
--Size, Lone Pairs and Bond Energy
--Hydrogen Halides
--Oxyacids and Oxyanions
--Other Halogen Compounds
20.8 The Group 8A Elements
--Structures of Xe Compounds
20.9 Challenge and Integrative Problems
Chapter 21 - Transition Metals and Coordination Chemistry
21.1 The Transition Metals: A Survey
--General Properties
--Electron Configurations
--Oxidation States
--Valence-State Electronegativity
--Ionization Energies
--Standard Reduction Potentials
--The 4d and 5d Transition Series --- Lanthanide Contraction
--Densities of Transition Metals
--Colors of Ions (Complexes)
--Magnetic Properties of Ions (Complexes)
21.2 The First-Row Transition Metals
21.3 Coordination Compounds
--Coordination Number
--Ligands
--Nomenclature
21.4 Isomerism
--Structural Isomerism
--Stereoisomerism
21.5 Bonding in Complex Ions: The Localized Electron Model
--Octahedral Complexes
--Linear Complexes
--Square Complexes
--Tetrahedral Complexes
21.6 The Crystal Field Model
--Octahedral Complexes
--Other Coordination Geometries
21.7 Complex Ion Reactions
21.8 Complex Ion Equilibria
21.9 Biologic Importance of Coordination Complexes
21.10 The 18-Electron Rule
21.11 Magnetic Susceptibility
21.12 Challenge Problems
Organic Chemistry
Chapter 1 Structure and Bonding
1.1 Atomic Structure: The nucleus
1.2 Atomic Structure: Orbitals
1.3 Atomic Structure: Electron Configurations --- the lowest-energy arrangement or ground-state electron configuration
1.5 The Nature of Chemical Bonds: Valence Bond Theory
1.6 Hybrid Orbitals
1.7 The Nature of Chemical Bonds: Molecular Orbital Theory
1.8 Drawing Chemical Structures --- condensed structures and skeletal structures.
Chapter 2 Polar Covalent Bond; Acids and Bases
2.1 Polar Covalent Bonds: Electronegativity
2.2 Polar Covalent Bonds: Dipole Moments, m
2.3 Formal Charges:
2.4 Resonances
2.5 Rules for Resonance Forms
2.6 Drawing Resonance Forms
2.7 Acids and Bases: The Bronsted-Lowry Definition
2.8 Acid and Base Strength
2.9 Predicting Acid-Base Reactions from pka values
2.10 Organic Acids and Organic Bases
2.11 Acids and Bases: The Lewis Definition
2.12 Noncovalent interactions: Intermolecular Forces
Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry
3.1 Functional Groups
3.2 Alkanes and Alkane Isomers
3.3 Alkyl Groups
3.4 Naming Alkanes
3.5 Properties of Alkanes
3.6 Conformations of Ethane
3.7 Conformations of Other Alkanes
Chapter 4 Organic Compounds: Cycloalkanes and Their Stereochemistry
4.1 Naming cycloalkanes
4.2 Cis-trans isomerism in cycloalkanes
4.3 Stability of cycloalkanes: Angle (Ring) strain --- due to expansion or compression of bond angles.
4.4 Conformations of cycloalkanes --- cyclohexanes
4.5 Axial and equatorial bonds in Cyclohexane
4.6 Conformation of monosubstituted cyclohexanes
4.7 Conformations of disubstituted cyclohexanes
Chapter 5 An Overview of Organic Reactions
5.1 Kinds of Organic Reactions
5.2 How organic reactions occurs: Mechanisms
5.3 Radical Reactions
5.4 Polar Reactions
5.6 Using curved arrows in polar reaction mechanisms
5.7 Describing a reaction: Equilibria, Rates, and Energy Changes
5.8 Describing a reaction: Bond dissociation energies (p156, Table 5.3).
Chapter 6 Alkenes: Structure and Reactivity
6.1 Calculating degree of unsaturation: the number of rings and/or multiple bonds present in the molecule.
6.2 Naming alkenes
6.3 Sequence rules: The E, Z designation
6.4 Stability of alkenes
6.5 Electrophilic addition reactions of alkene
Chapter 7 Alkenes: Reactions and Synthesis
7.1 Preparation of alkenes: elimination
7.2 Addition of halogen
7.3 Addition of hypohalous acids (HO-Cl or HO-Br) --- halohydrin formation
7.4 Addition of water: oxymercuration
7.5 Addition of water: hydroboration
7.6 Reduction: hydrogenation
7.7 Oxidation: cleavage to carbonyl compounds
7.8 Radical addition to alkenes: Polymer
Chapter 8 Alkynes: An Introduction to Organic Synthesis
8.1 Naming alkynes
8.2 Preparation of alkynes --- Elimination reactions of dihalides
8.3 Reaction of alkynes
8.4 Alkyne acidity --- Terminal alkynes are weakly acidic.
8.5 Alkylation of acetylide anions
8.6 An introduction to organic synthesis
Chapter 9 Stereochemistry
9.1 Enantiomers and the tetrahedral carbon
9.2 Chirality
9.3 Optical activity
9.4 Sequence rules for specifying configuration
9.5 Diastereomers --- stereoisomers that are not mirror images.
9.6 Meso compounds --- Having Chirality centers, but not achiral
9.7 Recemic mixture and the resolution of enantiomers
9.8 A review of isomerism
Chapter 10 Organohalides
10.1 Naming alkyl halides
10.2 Structure of alkyl halides
10.3 Preparing alkyl halides: Radical halogenations of alkanes
10.4 Preparing alkyl halides: Allylic bromination
10.5: Stability of allylic radical: Resonance Revisited
10.6: Preparing alkyl halides: From alcohol
10.7 Reactions of alkyl halides
Chapter 11 Reactions of Alkyl halides: Nucleophilic Substitutions and Eliminations
11.1 The discovery of nucleophilic substitution reactions --- Walden Inversion
11.2 The SN2 reaction --- Nucleophilic substitution reaction
11.3 Characteristics of the SN2 reaction
11.4 The SN1 reaction
11.5 Characteristics of the SN1 reaction
11.6 Elimination reactions: Zaitsev’s rule
Chapter 12 Structure Determination: Mass Spectrometry & Infrared Spectroscopy
12.1 Mass spectrometry of small molecules
12.2 Interpreting mass spectra
12.3 Mass Spectrometry of Some Common Functional Groups
12.4 Spectroscopy and the electromagnetic spectrum
12.5 Infrared Spectroscopy
12.6 Interpreting infrared spectra
12.7 Determine the structures for the following compounds.
Chapter 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy
13.1 Nuclear magnetic resonance spectroscopy
13.2 The nature of NMR absorption
13.3 Magnetic shielding by electrons
13.4 Nuclear magnetic resonance (NMR) spectrum
13.5 Chemical shifts in 1H NMR spectroscopy
13.6 Integration of 1H NMR absorption: proton counting
13.7 Spin-spin splitting in 1H NMR spectra
13.8 Introduction to 13C NMR Spectroscopy
13.9 Spectra practice questions
Chapter 14 Conjugated Compounds and Ultraviolet Spectroscopy
14.1 Stability of conjugated dienes
14.2 Electrophilic additions to conjugated dienes: Allylic carbocations
14.3 The Diels-alder cycloaddition reaction
14.4 Structure determination in conjugated systems: Ultraviolet spectroscopy
Chapter 15 Benzene and Aromaticity
15.1 Sources and names of aromatic compounds
15.2 Structure and stability of benzene: Molecular orbital theory
15.3 Aromaticity and the Huckel (4n + 2) rule
15.4 Aromatic ions
15.5 Aromatic heterocycles
15.6 Why 4n + 2
Chapter 16 Chemistry of Benzene: Electrophilic Aromatic substitution
16.1 Electrophilic aromatic substitution reactions
16.2 Other aromatic substitutions
16.3 The Friedel-Crafts reaction
16.4 Substituent effects in substituted aromatic rings
16.5 An explanation of substituent effects
16.6 Trisubstituted Benzenes: additivity of effects
16.7 Oxidation of Aromatic compounds --- alkylbenzene side chains
Chapter 17 Alcohols and Phenols
17.1 Naming alcohols and phenols
17.2 properties of alcohols and phenols
17.3 Preparation of alcohols
17.4 Alcohols from reduction of carbonyl compounds
17.5 Alcohols from reactions of carbonyl compounds with Grignard Reagents
17.6 Reactions of alcohols
17.7 Oxidation of alcohols
Chapter 18 Ethers and Epoxides; Thiols and Sulfides
18.1 Names and properties
18.2 Physical properties
18.3 Synthesis of ethers
Chapter 19 Aldehydes and ketones: Nucleophilic addition Reactions
19.1 Naming aldehyde and ketone
19.2 Preparation of aldehyde and ketone
19.3 Oxidation of aldehydes and ketones
19.4 Nucleophilic addition reactions of aldehydes and ketones
19.5 Nucleophilic addition of H2O
19.6 Nucleophilic addition of HCN
19.7 Nucleophilic addition of Grignard and hydride reagents
19.8 Nucleophilic addition of amines
19.9 Nucleophilic addition of hydrazine
19.10 Nucleophilic addition of alcohols
19.11 Nucleophilic addition phosphorus ylides
Chapter 20 Carboxylic Acids and Nitriles
20.1 Naming carboxylic acids
20.2 Structure and properties of carboxylic acids
20.3 Substituent effects on acidity
20.4 Preparation of carboxylic acids
20.5 Reactions of carboxylic acids
Chapter 21 Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Reactions
21.1 Naming carboxylic acid derivatives
21.2 Nucleophilic acyl substitution reactions
21.3 Nucleophilic acyl substitution reactions of carboxylic acids
21.4 Chemistry of acid halides
21.5 Chemistry of acid anhydrides
21.6 Chemistry of esters
21.7 Chemistry of amides
21.8 Polyamides and polyesters: step-growth polymers
Chapter 22 Carbonyl Alpha-Substitution Reactions
22.1 Keto-enol tautomerism
22.2 Alpha halogenations of aldehydes and ketone
22.3 Alpha bromination of carboxylic acids: the Hell-Volhard-Zelinskii reaction
22.4 Acidity of alpha hydrogen atoms: Enolate ion formation
22.5 Reactivity of enolate ions
22.6 Alkylation of enolate ions
Chapter 23 Carbonyl Condensation Reactions
23.1 Carbonyl Condensations: the aldol reaction
23.2 Carbonyl Condensation versus alpha substitutions
23.3 Dehydration of aldol products: synthesis of enones
23.4 Using aldol reactions in synthesis
23.5 Mixed aldol reactions
23.6 Intramolecular aldol reactions: Forming a cyclic product.
23.7 The Claisen condensation reaction
23.8 Mixed Claisen condemnation
23.9 Intramolecular Claisen condensation: The Dieckmann cyclization
23.10 Conjugate carbonyl additions: the Michael reaction
23.11 Carbonyl condensations with enamines: the Stork reaction
23.12 The Robinson annulations reaction
Chapter 24 Amines and Heterocycles
24.1 Naming amines
24.2 Properties of amines
24.3 Basicity of amines
24.4 Basicity of substituted arylamines
24.5 Henderson-Hasselbalch equation
24.6 Synthesis of amines
24.7 Reactions of amines
24.8 Reactions of Arylamines
24.9 Heterocycles
Chapter 25 Biomolecules: Carbohydrates
25.1 Classification of carbohydrates
25.2 Depicting carbohydrate stereochemistry: Fischer projections
25.3 D, L Sugars
25.4 Configuration of the aldoses
25.5 Cyclic structures of monosaccarides: anomers
25.6 Reactions of monosaccharides
25.7 The eight essential monosaccharides
25.8 Disaccharides
25.9 Polysaccharides and their synthesis
Chapter 26 Biomolecules: Amino Acids, Peptides, and Proteins
26.1 Structures of amino acids
26.2 Amino acids, the Henderson-Hasselbalch equation, and isometric points
26.3 Synthesis of amino acids
26.4 Peptides and proteins
26.5 Protein structure
26.6 Enzymes and coenzymes
Chapter 27 Biomolecules: Nucleic Acids
27.1 Nucleotides and nucleic acids
27.2 Base Pairing in DNA: the Watson-Crick Model
Chapter 28 Synthetic Polymers
28.1 Chain-growth polymers
28.2 Stereochemistry of polymerization: Ziegler-Natta catalyst
28.3 Copolymer
28.4 Step-growth polymers
US National Olympiad Exam Lab Preparations
LP.1 Introduction
LP.2 Common Laboratory Task Types
LP.3 Qualitative Analysis and Assignment of Unknowns
LP.4 Quantitative Analysis and Titration
LP.5 Recommended Lab Practices
--Lab Practice 1
--Lab Practice 2
--Lab Practice 3
--Lab Practice 4
--Lab Practice 5
--Lab Practice 6
--Lab Practice 7
--Lab Practice 8
--Lab Practice 9
--Lab Practice 10
--Lab Practice 11
--Lab Practice 12
--Lab Practice 13
--Lab Practice 14
--Lab Practice 15
--Lab Practice 16
--Lab Practice 17
--Lab Practice 18
--Lab Practice 19
--Lab Practice 20
--Lab Practice 21
--Lab Practice 22
--Lab Practice 23
--Lab Practice 24
