INTERNATIONAL CHEMISTRY OLYMPIAD

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The International Chemistry Olympiad (I Cho) is an annual academic competition for high school students. It is one of the International science Olympiads.
The first I Cho was held in Prague, Czechoslovakia, in 1968. The event has been held every year since then, with the exception of 1971. The delegations that attended the first events were mostly countries of the former Eastern bloc and it was not until 1980, the 12th annual International Chemistry Olympiad, that the event was held outside of the bloc in Austria.

STRUCTURE AND RULES OF THE COMPETITION




     An International Chemistry Olympiad medal

Each delegation consists of up to four students and two mentors (one of them is designated as the head of the delegation or "head mentor"). A delegation may also include a handful of guests and scientific observers. Students must be under the age of 20 and must not be enrolled as regular students in any post-secondary education institution. The International Information Center of the International Chemistry Olympiad is based in Bratislava, Slovakia.
Countries who wish to participate in the I Cho must send observers to two consecutive Olympiads before their students can participate in the event. A total of 68 countries took part in the 38th I Cho: 67 as participants and 1 as an observer.
The competition consists of two examinations, a theoretical examination and a practical examination. Both have durations of up to 5 hours, and are held on separate days with the practical examination usually being before the theoretical examination. The theoretical examination has a value of 60 points and the practical examination has a value of 40 points. Each examination is evaluated independently from the other and the sum of the results of the examinations determines a participant's overall result. A scientific jury, which is installed by the host country, suggests the tasks. The international jury, which consists of the 2 mentors from each of the participating countries, discusses the competition tasks and translates them into the language of their students' preference.
Students receive the examinations translated into their languages of preference. It is the duty of the mentors to translate the examinations from English before they are given to the participants. After the examinations are held and evaluated by a committee appointed by the host country and before awards are presented, mentors discuss the evaluation of the exams with judges of the committee to assure fairness in their evaluation. Because the mentors review the examinations before they are given to participants, any communication between the mentors and the students is strictly forbidden prior to the completion of both exams, and the students are required to surrender any mobile phones and laptop computers to the organizer.
The syllabus of the competition contains subjects from several areas of chemistry, including organic chemistry, inorganic chemistry, physical chemistry, analytically chemistry, biochemistry, and spectroscopy. Though the majority of these subjects are included in most secondary school chemistry programs, for the most part, they are evaluated at a much deeper level and many may require a level of knowledge and understanding comparable to that of post-secondary education. In addition, the host country of each I Cho issues a set of preparatory problems well in advance of the competition every year. These preparatory problems cover specific topics in considerable more depth than typical post-secondary education. Preparation for the International Chemistry Olympiad demands a high level of understanding and interest in chemistry and an outstanding ability to relate chemical subjects with one another as well as with the practical world.



                                  A gold medal from the 40th I Cho

All participants are ranked based on their individual scores and no official team scores are given. Gold medals are awarded to the top 10% of students, silver medals are awarded to the next 20% of students, and bronze medals are awarded to the next 30% of students. Honorable mentions are awarded to participants that do not win a medal but score a perfect problem in either the theoretical or the practical examination. One special award is given to the student that achieves the highest score overall. Two separate special awards are given to the students who get the best score in the theoretical and practical examinations. Occasionally, another special award is given to the top-scoring female student as well.
These events are also outstanding opportunities for the students to meet people from all around the world who share similar interests, to visit different places, and to get in touch with different cultures. As the aims of the competition establish, the I Cho competitions help to enhance friendly relations among young people from different countries; they encourage cooperation and international understanding.


PREPRATION FOR THE COMPETITION

While each country is free to choose its team by whatever means it deems appropriate, the selection process usually involves holding regional and national Olympiad competitions. Many countries hold "training camps" for its top students, where mentors from the country give the students accelerated college-level courses in chemistry with an emphasis on the topics covered in that year's preparatory problems as well as practical training. It is agreed that such training programs must not exceed a total duration of two weeks but there are allegations every year that some countries exceed this limit by months or even years. Another concern is that some countries tend to bring the same students to the competition year after year, which helps them win better medals. Although some believe that this is against the spirit of the Olympiad, many nations find it hard to justify leaving their best students at home.


HISTORY




The idea of the International Chemistry Olympiad was developed in the former Czechoslovakia in 1968. It was designed with the aim to increase the number of international contacts and the exchange of information between nations. Invitations were sent by the Czech national committee to all socialist countries, except Romania. However, in May 1968, relations between Czechoslovakia and the Soviet Union became so delicate that only Poland and Hungary participated in the first international competition. The first International Chemistry Olympiad took place in Prague between 18 and 21 June, 1968. Each of the three participating countries sent a team of six pupils, and four theoretical tasks were to be solved. Guidelines for the next competitions were already suggested. The second chemistry Olympiad took place in 1969 in Poland, and Bulgaria also participated. Each team consisted of five pupils, and an experimental competition was added. The decision was made to invite more socialist countries to future competitions and to limit the number of pupils to four. The third Olympiad in 1970 was organized in Hungary with the GDR, Romania and the Soviet Union as new countries. In this competition, more than three prizes were distributed to the pupils.
There was no Olympiad held in 1971, as at the end of the competition in 1970, an organizer and host for the next event could not be agreed on. This was solved for the next three years by diplomatically agreeing on the Soviet Union to host 1972, Bulgaria in 1973, and Romania in 1974. 1972 was the first time where preparation tasks for the International Chemistry Olympiad were created. Also, at a jury session, it was suggested that invitations should be sent to Vietnam, Mongolia, and Cuba. Unfortunately though, these invitations were not sent, leaving seven to compete in 1973.
In 1974, Romania invited Sweden and Yugoslavia to the Olympiad in Bucharest and Germany and Austria sent observers. The Federal Republic of Germany was the first NATO-country with an observer present and this was only able to occur because the Brandt government had contracts in the East. Thus, in 1975, West Germany, Austria, and Belgium also participated in the International Chemistry Olympiad.
The first Olympiad in a non-socialist country took place 1980 in Linz in Austria, although the Soviet Union did not participate. Since then the number of the participating countries has increased steadily. In 1980, only 13 nations took part but this number increased to 21 by the 1984 Olympiad in Frankfurt/Main. With the fall of the Iron Curtain and the break-up of the Soviet Union into independent states in the early 1990s, the number of participants increased again. In addition, the increasing interest of Asian and Latin American countries became apparent with the numbers of participants. Altogether 47 delegations participated in 1998. Presently, 68 countries participate in the International Chemistry Olympiad.


FUTURE INTERNATIONAL OLYMPIAD

   PAST INTERNATIONAL CHEMISTRY OLYMPIAD

Preparatory problems, final results, and the theoretical and practical examinations from each competition can be found on the respective I Cho’s website.




I CHO REGULATIONS

  The very beginning .... 
On May 15th, 1968 a meeting was organized in Ostrava (Czechoslovakia) with the aim to create some basic rules for the international competition, called later as International Chemical Olympiad. Three countries took part, with representatives of the National committees of the countries. The report gave answers to some fundamental questions that formed later a basis for the preliminary regulations of the new international competition. The first regulations were very simple and consisted of seven points. 
1.   Competitions of this kind should promote friendship and co-operation among the pupils, closer contacts among the young scientific workers, exchange of pedagogical and scientific experience.
2.   The organizer of the competition is the Ministry of Education of the organizing country.
3.   The competition should be organized at the end of the school year.
4.   National team consists of pupils and accompanying persons (teachers).
5.   Pupils of the secondary school without a special chemical orientation can only participate in the competition.
6.   The IChO is a competition of individual pupils, not a competition of teams.
7.   The IChO will consist of two parts: theoretical and experimental.

These first regulations were approved during the 1st International Chemistry Olympiad on 21st of June 1968. 
Compare the first regulations with those approved by the International Jury of the 42nd  International Chemistry Olympiad in Japan.




SYLLABUS



Theoretical part

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. The atom
1.1.
 Introduction

1.1.1.
 Counting of nucleons
 1

1.1.2.
 Isotopes
 1
1.2.
 The hydrogen atom

1.2.1.
 Concept of energy levels
 1

1.2.2.
 Shape of s-orbitals
 1

1.2.3.
 Shape and orientation of p-orbitals
 1

1.2.4.
 Shape and orientation of d-orbitals
 3

1.2.5.
 Understanding the simplest Schrodinger equation
 3

1.2.6.
 Square of the wave function and probability
 3

1.2.7.
 Quantum numbers (n, l, ml)
 3
1.3.
 Radioactivity

1.3.1.
 Types of radioactivity
 1

1.3.2.
 Radioactive decay
 1

1.3.3.
 Nuclear reactions
 2




2. Chemical bonding
2.1.
 VSEPR " Simple molecular structures with

2.1.1.
 no more than four electron pairs about central atom
 1

2.1.2.
 with central atom exceeding the "octet rule?
 3
2.2.
 Delocalization and resonance
 3
2.3.
 Hybrid orbital theory
 3
2.4.
 Molecular orbital theory

2.4.1.
 molecular orbital diagram (H2 molecule)
 3

2.4.2.
 molecular orbital diagram (N2 and O2 molecules)
 3

2.4.3.
 bond orders in O2, O2?, O2+
 3

2.4.4.
 unpaired electrons and paramagnetism
 3




3. Chemical calculations

3.1.1.
 Balancing equations
 1

3.1.2.
 Stoichiometric calculations
 1

3.1.3.
 Mass and volume relations (including density)
 1

3.1.4.
 Empirical formula
 1

3.1.5.
 Avogadro?s number
 1

3.1.6.
 Concentration calculations
 1




4. Periodic trends
4.1.
 Electron configuration

4.1.1.
 Pauli exclusion principle
 1

4.1.2.
 Hund?s Rule
 1

4.1.3.
 Main group elements
 1

4.1.4.
 Transition metal elements
 1

4.1.5.
 Lanthanide and actinide metals
 3
4.2.
 Electronegativity
 1
4.3.
 Electron affinity
 2
4.4.
 First ionization energy
 1
4.5.
 Atomic size
 1
4.6.
 Ion size
 1
4.7.
 Highest oxidation number
 1




5. Inorganic Chemistry
5.1.
 Introduction

5.1.1.
 Trends in physical properties of elements (Main groups)


5.1.1.1.
 melting point
 1


5.1.1.2.
 boiling point
 1


5.1.1.3.
 metal character
 1


5.1.1.4.
 magnetic properties
 3


5.1.1.5.
 electrical conductivity
 2

5.1.2.
 Oxidation number
 1

5.1.3.
 Nomenclature


5.1.3.1.
 main group compounds
 1


5.1.3.2.
 transition metal compounds
 1


5.1.3.3.
 simple metal complexes
 3
5.2.
 Groups 1 and 2

5.2.1.
 Trend in reactivity of (heavy elements more reactive)
 1

5.2.2.
 Products of reaction with


5.2.2.1.
 water
 1


5.2.2.2.
 halogens
 1


5.2.2.3.
 oxygen
 2

5.2.3.
 Basicity of oxides
 1

5.2.4.
 Properties of hydrides
 3

5.2.5.
 Other compounds, properties and oxidation states
 3
5.3.
 Groups 13 " 18 and Hydrogen

5.3.1.
 Binary molecular compounds of hydrogen


5.3.1.1.
 Formulae
 1


5.3.1.2.
 Acid-base properties of CH4, NH3, H2O, H2S
 1


5.3.1.3.
 Other properties
 3

5.3.2.



Group 13


5.3.2.1
 The oxidation state of boron and aluminium in their oxides and chlorides is +3
 1


5.3.2.2.
 The acid-base properties of aluminium oxide/hydroxide
 2


5.3.2.3.
 Reaction of boron(III) oxide with water
 3


5.3.2.4.
 Reaction of boron(III) chloride with water
 3


5.3.2.5.
 Other compounds, properties and oxidation states
 3

5.3.3.
 Group 14


5.3.3.1.
 The oxidation state of Si in its chloride and oxide is +4
 1


5.3.3.2.
 The +2 and +4 oxidation states of carbon, tin and lead, the acid-base and redox properties of the oxides and chlorides
 2


5.3.3.3.
 Other compounds, properties and oxidation states
 3

5.3.4.
 Group 15


5.3.4.1.
 Phosphorus(+5) oxide and chloride, and their reaction with water
 2


5.3.4.2.
 Phosphorus(+3) oxide and chloride, and their reaction with water
 2


5.3.4.3.
 Oxides of nitrogen



a. Reaction of NO to form NO2
 1



b. Dimerization of NO2
 1



c. Reaction of NO2 with water
 1


5.3.4.4.
 Redox properties of



a. HNO3 and nitrates
 1



b. HNO2 and NH2NH2
 3


5.3.4.5.
 Bi(+5) and Bi(+3)
 3


5.3.4.6.
 Other compounds, properties and oxidation states
 3

5.3.5.
 Group 16


5.3.5.1.
 The +4 and +6 oxidation states of sulfur, reaction of their oxides with water, properties of their acids
 1


5.3.5.2.
 Reaction of thiosulfate anion with I2
 3


5.3.5.3.
 Other compounds, properties and oxidation states
 3

5.3.6.
 Group 17 (Halogens)


5.3.6.1.
 Reactivity and oxidant strength decreases from F2 to I2
 1


5.3.6.2.
 Acid-base properties of the hydrogen halides
 1


5.3.6.3.
 The oxidation state of fluorine in its compounds is "1
 1


5.3.6.4.
 The "1, +1, +3, +5, +7 oxidation states of chlorine
 1


5.3.6.5.
 Mononuclear oxoanions of chlorine
 2


5.3.6.6.
 Reactions of halogens with water
 3


5.3.6.7.
 Reaction of Cl2O and Cl2O7 with water
 3


5.3.6.8.
 Other compounds, properties and oxidation states
 3

5.3.7.
 Group 18
 3
5.4.
 Transition elements

5.4.1.
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)
 1

5.4.2.
 Colours of ions listed above in aqueous solution
 2

5.4.3.
 Insolubility of Ag, Hg and Cu in HCl
 2

5.4.4.
 M2+ arising by dissolution of the other metals in HCl
 2

5.4.5.
 Cr(OH)3 and Zn(OH)2 are amphoteric and the other +2
oxides/hydroxides of the metals listed above are basic
 2

5.4.6.
 MnO4? and Cr2O72? are strong oxidants in acid solution
 1

5.4.7.
 pH dependence of products of MnO4? acting as oxidant
 2

5.4.8.
 Interconversion between CrO42? and Cr2O72?
 3

5.4.9.
 Other compounds, properties and oxidation states
 3
5.5.
 Lanthanides and actinides
 3
5.6.
 Coordination chemistry including stereochemistry

5.6.1.
 Definition of coordination number
 1

5.6.2.
 Writing equations for complexation reactions given all formulae
 1

5.6.3.
 Formulae of common complex ions


5.6.3.1.
 Ag(NH3)2+
 1


5.6.3.2.
 Ag(S2O3)23?
 3


5.6.3.3.
 FeSCN2+
 3


5.6.3.4.
 Cu(NH3)42+
 1


5.6.3.5.
 Other complex ions
 3

5.6.4.
 (6.5) Ligand field theory (eg and t2g terms, high and low spin)
 3

5.6.5.
 Stereochemistry


5.6.5.1.
 (6.7) cis and trans
 3


5.6.5.2.
 enantiomers
 3
5.7.
 Selected industrial processes

5.7.1.
 Preparation of H2SO4
 1

5.7.2.
 Preparation of NH3
 1

5.7.3.
 Preparation of Na2CO3
 2

5.7.4.
 Preparation of Cl2 and NaOH
 2

5.7.5.
 Preparation of HNO3
 2




6. Physical chemistry
6.1.
 Gases

6.1.1.
 Ideal gas law
 1

6.1.2.
 van der Waal?s gas law
 3

6.1.3.
 definition of partial pressure
 2

6.1.4.
 Dalton?s Law
 3
6.2.
 Thermodynamics

6.2.1.
 First Law


6.2.1.1.
 Concept of system and surroundings
 2


6.2.1.2.
 Energy, heat and work
 2

6.2.2.
 Enthalpy


6.2.2.1.
 Relationship between internal energy and enthalpy
 3


6.2.2.2.
 Definition of heat capacity
 2


6.2.2.3.
 Difference between Cp and Cv (ideal gas only)
 3


6.2.2.4.
 Enthalpy is a state property (Hess?s Law)
 2


6.2.2.5.
 Born-Haber cycle for ionic compounds
 3


6.2.2.6.
 Use of standard formation enthalpies
 2


6.2.2.7.
 Enthalpies of solution and solvation
 3


6.2.2.8.
 Bond enthalpies (definition and use)
 2

6.2.3.
 Second Law (Entropy and Free Energy)


6.2.3.1.
 Entropy definition (dq / T)
 3


6.2.3.2.
 Entropy and disorder
 3


6.2.3.3.
 Entropy definition (S = k ln W)
 3


6.2.3.4.
 Gibbs energy definition (DG = DH " TDS)
 3


6.2.3.5.
 Using DG to predict direction of natural change
 3


6.2.3.6.
 Relationship between DGњ and equilibrium constant K
 3
6.3.
 Equilibrium

6.3.1.
 Acid-base


6.3.1.1.
 Arrhenius definitions of acids and bases
 1


6.3.1.2.
 Bronsted-Lowry definitions
 1


6.3.1.3.
 Conjugate acids and bases
 1


6.3.1.4.
 pH definition
 1


6.3.1.5.
 Kw definition
 1


6.3.1.6.
 Ka and Kb as a measure of acid and base strength
 1


6.3.1.7.
 Acidity or basicity of ions
 1


6.3.1.8.
 Calculation of pH from pKa(weak acid)
 1


6.3.1.9.
 Calculation of pH of a simple buffer solution
 2

6.3.2.
 Gas phase


6.3.2.1.
 Equilibrium constant in partial pressures
 3


6.3.2.2.
 Relating Kp and Kc
 3

6.3.3.
 Solubility


6.3.3.1.
 Solubility constant (product) definition (Ksp)
 2


6.3.3.2.
 Calculation of solubility in water from Ksp
 2

6.3.4.
 Compleximetric


6.3.4.1.
 Complex formation constant (definition)
 3


6.3.4.2.
 Problems involving compleximetric equilibria
 3


6.3.4.3.
 Lewis acids and bases
 3


6.3.4.4.
 Hard and soft Lewis acids and bases
 3

6.3.5.
 Phase


6.3.5.1.
 Temperature dependence of vapour pressure
 3


6.3.5.2.
 Clausius-Clapeyron equation
 3


6.3.5.3.
 Single component phase diagrams



a. triple point
 3



b. critical point
 3


6.3.5.4.
 liquid-vapour system



a. ideal and nonideal systems
 3



b. diagram
 3



c. use in fractional distillation
 3


6.3.5.5.
 Henry?s Law
 3


6.3.5.6.
 Raoult?s Law
 3


6.3.5.7.
 Deviation from Raoult?s Law
 3


6.3.5.8.
 Boiling point elevation
 3


6.3.5.9.
 Freezing point depression
 3


6.3.5.10.
 Osmotic pressure
 3


6.3.5.11.
 Partition coefficient
 3


6.3.5.12.
 Solvent extraction
 3

6.3.6.
 Multiple


6.3.6.1.
 Calculation of pH for multiprotic acids
 3


6.3.6.2.
 Calculation of pH for weak acid mixtures
 3
6.4.
 Electrochemistry

6.4.1.
 Electromotive force (definition)
 1

6.4.2.
 First kind electrodes
 1

6.4.3.
 Standard electrode potential
 1

6.4.4.
 Nernst equation
 3

6.4.5.
 Second kind electrodes
 3

6.4.6.
 Relationship between DG and electromotive force
 3




7. Chemical kinetics (Homogeneous reactions)
7.1.
 Introduction

7.1.1.
 Factors affecting reaction rate
 1

7.1.2.
 Reaction coordinates and the basic idea of a transition state
 1
7.2.
 Rate law

7.2.1.
 Differential rate law
 2

7.2.2.
 Concept of reaction order
 2

7.2.3.
 Rate constant definition
 2

7.2.4.
 First order reactions


7.2.4.1.
 Dependence of concentration on time
 3


7.2.4.2.
 Concept of half life
 3


7.2.4.3.
 Relationship between half life and rate constant
 3


7.2.4.4.
 Calculation of first order rate constant from



a. differential rate law
 3



b. integrated rate law
 3


7.2.4.5.
 Rate constant for second and third order reactions
 3
7.3.
 Reaction mechanisms

7.3.1.
 Concept of molecularity
 3

7.3.2.
 Rate-determining step
 3

7.3.3.
 Basic concepts of collision theory
 3

7.3.4.
 Opposing parallel and consecutive reactions
 3

7.3.5.
 Arrhenius?s law
 3


7.3.5.1.
 Definition of activation energy
 3


7.3.5.2.
 Calculation of activation energy
 3




8. Spectroscopy
8.1.
 UV/visible

8.1.1.
 Identification of aromatic compound
 3

8.1.2.
 Identification of chromophore
 3

8.1.3.
 Dyes: colour vs structure
 3

8.1.4.
 Beer?s Law
 3
8.2.
 Infrared

8.2.1.
 Interpretation using a table of frequencies
 3

8.2.2.
 Recognition of hydrogen bonds
 3
8.3.
 x-Ray

8.3.1.
 Bragg?s Law
 3

8.3.2.
 Concept of


8.3.2.1.
 coordination number
 3


8.3.2.2.
 unit cell
 3

8.3.3.
 Solid structures


8.3.3.1.
 NaCl
 3


8.3.3.2.
 CsCl
 3


8.3.3.3.
 metals
 3
8.4.
 NMR

8.4.1.
 General Concepts


8.4.1.1.
 chemical shift
 3


8.4.1.2.
 spin-spin coupling and coupling constants
 3


8.4.1.3.
 integration
 3

8.4.2.
 Interpretation of a simple 1H spectrum (like ethanol)
 3

8.4.3.
 Identification of o- and p-disubstituted benzene
 3

8.4.4.
 Interpretation of simple spectra of 13C (proton decoupled) and other 1/2 spin nuclei
 3
8.5.
 Mass spectrometry

8.5.1.1.
 Recognition of molecular ion
 3

8.5.1.2.
 Recognition of fragments with the help of a table
 3

8.5.1.3.
 Recognition of typical isotope distribution
 3




9. Organic Chemistry
9.1.
 Introduction

9.1.1.
 (3.1.1) Alkane naming (IUPAC)
 1

9.1.2.
 Trends in boiling points of


9.1.2.1.
 (3.1.3) alkanes with structure
 1


9.1.2.2.
 (3.7.1) alcohols vs ethers due to hydrogen-bonding
 1

9.1.3.
 (3.3.1, 3.4.1) Geometry at singly, doubly, and triply bonded carbon
 1

9.1.4.
 Identification of common functional groups
 1

9.1.5.
 Isomerism of alkenes


9.1.5.1.
 cis-trans
 1


9.1.5.2.
 E/Z
 3

9.1.6.
 Enantiomers


9.1.6.1.
 Optical activity
 2


9.1.6.2.
 R/S nomenclature
 3
9.2.
 Reactivity

9.2.1.
 Alkanes


9.2.1.1.
 reaction with halogens



a. products
 1



b. free radical mechanism (initiation, termination)
 2


9.2.1.2.
 Cycloalkanes



a. names
 2



b. Strain in small rings
 3



c. chair/boat conformations of cyclohexane
 3

9.2.2.
 Alkenes


9.2.2.1.
 Products from Br2, HBr and H2O/H+
 1


9.2.2.2.
 Markownikoff?s rule
 2


9.2.2.3.
 Mechanism involving carbocation intermediates
 3


9.2.2.4.
 Relative stability of carbocations
 3


9.2.2.5.
 1,4 addition to dienes
 3

9.2.3.
 Alkynes


9.2.3.1.
 Acidity relative to alkenes
 3


9.2.3.2.
 Differences in chemical properties from alkenes
 2

9.2.4.
 Benzene


9.2.4.1.
 formula
 1


9.2.4.2.
 stabilization by resonance
 1


9.2.4.3.
 electrophilic substitution (nitration, halogenation)



a. directing effect of first substituent
 3



b. effect of first substituent on reactivity
 3



c. explanation of substituent effects
 3

9.2.5.
 Halogen compounds


9.2.5.1.
 Nomenclature of monofunctional
 1


9.2.5.2.
 Substitution reactions



a. giving alcohols
 3



b. in which halogen is exchanged
 3



c. reactivity




i. primary vs secondary vs tertiary
 3




ii. aliphatic vs aromatic
 3



d. SN1 and SN2 mechanisms
 3


9.2.5.3.
 Elimination reactions
 2


9.2.5.4.
 Competition of elimination and substitution
 2

9.2.6.
 Alcohols


9.2.6.1.
 Nomenclature of monofunctional
 1


9.2.6.2.
 Comparison of acidity of alcohols and phenols
 2


9.2.6.3.
 Dehydration to alkenes
 1


9.2.6.4.
 Esters with inorganic acid
 2


9.2.6.5.
 Oxidation reactions
 1

9.2.7.
 Aldehydes and ketones


9.2.7.1.
 Nomenclature of monofunctional
 1


9.2.7.2.
 Oxidation of aldehydes
 1


9.2.7.3.
 Reduction to alcohols (LiAlH4, NaBH4)
 3


9.2.7.4.
 Keto/enol tautomerism
 3


9.2.7.5.
 Nucleophilic addition reactions with



a. HCN
 3



b. RNH2 (R = alkyl, HO, NH2)
 3



c. enolate anions (aldol condensation)
 3



d. alcohols to form acetals/ketals
 3



e. Grignard reagents
 3

9.2.8.
 Carboxylic acids and their derivatives


9.2.8.1.
 Nomenclature of carboxylic acids and their derivatives (esters, acid halides, amides)
 2


9.2.8.2.
 Acidity strength related to inductive effects
 3


9.2.8.3.
 Preparation of carboxylic acids by hydrolysis of



a. esters (including soaps)
 1



b. amides
 2



c. nitriles
 3


9.2.8.4.
 Reaction of carboxylic acids



a. with alcohols to form esters
 1



b. to form acid chlorides
 3



c. to form anhydrides
 3


9.2.8.5.
 Reaction of acid chlorides to form amides
 3


9.2.8.6.
 Mechanism of esterification
 3


9.2.8.7.
 Multifunctional acids (hydroxyacids, ketoacids)
 3


9.2.8.8.
 Polycarboxylic acids
 3

9.2.9.
 Amines


9.2.9.1.
 Nomenclature



a. simple amines
 1



b. recognition of primary, secondary, tertiary
 1


9.2.9.2.
 Basicity



a. As a property of an amine
 1



b. Comparison of basicity of aliphatic and aromatic
 3



c. Comparison of basicity of amines and amides
 3



d. Preparation of amines




i. from halides
 3




ii. from aromatic nitro compounds
 3




iii. from amides (by hydrolysis)
 3


9.2.9.3.
 Diazotization



a. of aliphatic amines
 3



b. of aromatic amines
 3





10. Polymers
10.1.
 Synthetic

10.1.1.
 Addition polymers


10.1.1.1.
 polystyrene
 2


10.1.1.2.
 polyethene
 1


10.1.1.3.
 chain mechanism of formation
 2

10.1.2.
 Condensation polymers


10.1.2.1.
 polyesters
 2


10.1.2.2.
 polyamides
 2

10.1.3.
 Silicones
 3

10.1.4.
 Concept of cross-linking and its affect on properties
 3
10.2.
 Natural

10.2.1.
 Silicates
 3

10.2.2.
 Rubber
 3




11. Biochemistry
11.1.
 Carbohydrates

11.1.1.
 Glucose and fructose


11.1.1.1.
 chain formulae
 1


11.1.1.2.
 Fischer projections
 2


11.1.1.3.
 Haworth formulae
 3

11.1.2.
 Difference between starch and cellulose
 2

11.1.3.
 Difference between a- and b- D glucose
 2
11.2.
 Fats

11.2.1.
 Structure of fats in relationship to properties
 2

11.2.2.
 Formula of glycerol
 1
11.3.
 Nitrogen-containing Compounds of Biological Importance

11.3.1.
 Amino acids


11.3.1.1.
 Ionic structure
 1


11.3.1.2.
 Isoelectric point
 3


11.3.1.3.
 20 amino acids (classification with structures provided)
 2


11.3.1.4.
 Separation by electrophoresis
 3


11.3.1.5.
 The peptide linkage
 1

11.3.2.
 Proteins


11.3.2.1.
 Primary structure
 1


11.3.2.2.
 ?S-S- bridges
 3


11.3.2.3.
 Sequence analysis
 3


11.3.2.4.
 Secondary structure
 3


11.3.2.5.
 Details of a-helix structure
 3


11.3.2.6.
 Tertiary structure
 3


11.3.2.7.
 Denaturation (change in pH, temperature, metals, ethanol)
 2

11.3.3.
 Nuclei Acids and Protein Synthesis


11.3.3.1.
 Pyrimidine and purine
 3


11.3.3.2.
 Nucleosides and nucleotides
 3


11.3.3.3.
 Formulae of pyrimidine and purine bases
 3


11.3.3.4.
 Difference between ribose and 2-deoxyribose
 3


11.3.3.5.
 Base combination CG and AT (hydrogen-bonding)
 3


11.3.3.6.
 Difference between DNA and RNA
 3


11.3.3.7.
 Difference between mRNA and tRNA
 3
11.4.
 Enzymes

11.4.1.1.
 General properties, active centers
 3

11.4.1.2.
 Nomenclature, kinetics, coenzymes, function of ATP
 3




12. Analytical chemistry
12.1.
 Titrations

12.1.1.
 acid-base


12.1.1.1.
 Titration curve; pH (strong and weak acid)
 2


12.1.1.2.
 Choice of indicators for acidimetry
 2

12.1.2.
 Redox titration
 3
12.2.
 Qualitative analysis

12.2.1.
 Ions (Inorganic)


12.2.1.1.
 Identification of Ag+, Ba2+, Cl?, SO42?
 2


12.2.1.2.
 Identification of other anions and cations
 3

12.2.2.
 Organic functional groups


12.2.2.1.
 Lucas reagent (1-, 2-, 3-alcohols)
 3


12.2.2.2.
 Iodoform reaction
 3


12.2.2.3.
 Identification of primary, secondary, tertiary,
quarternary amines in the laboratory
 3
12.3.
 Chromatographic methods of separation
 3




 

Experimental part




Level 1:
 is assigned to the basic experimental activities which are supposed to be mastered by competitors very well
Level 2:
 is assigned to the activities which are parts of school experimental exercises in developed countries and the authors of IChO tasks may incorporate them into the tasks without being bounded to mention it in advance
Level 3:
 is assigned to such activities which are not in the chemistry syllabus in the majority of participating countries and the authors are obliged to mention them in the set of preparatory tasks
If the organizer wants to apply a technique which is not mentioned in the above syllabus, this technique is set to level 3 automatically.



1. Synthesis of inorganic and organic compounds



1.1.
 Heating with burners and hotplates
 1
1.2.
 Heating of liquids
 1
1.3.
 Handling the work with inflammable substances and materials
 1
1.4.
 Measuring of masses (analytical balance)
 1
1.5.
 Measuring of volumes of liquids (measuring cylinder, pipette, burette)
 1
1.6.
 Preparation of solutions from a solid compound and solvent
 1
1.7.
 Mixing and dilution of solutions
 1
1.8.
 Mixing and stirring of liquids
 1
1.9.
 Using mixer and magnetic stirrer
 2
1.10.
 Using a dropping funnel
 1
1.11.
 Syntheses in flat bottom vessels " general principles
 1
1.12.
 Syntheses in round bottom vessels " general principles
 1
1.13
 Syntheses in a closed apparatus " general principles
 1
1.14.
 Using microscale equipment for synthesis
 3
1.15.
 Apparatus for heating of reaction mixture under reflux
 2
1.16.
 Apparatus for distillation of liquids at normal pressure
 2
1.17.
 Apparatus for distillation of liquids at reduced pressure
 2
1.18.
 Apparatus for steam distillation
 3
1.19.
 Filtration through flat paper filter
 1
1.20.
 Filtration through a folded paper filter
 1
1.21.
 Handling a water vacuum pump
 1
1.22.
 Filtration through a Büchner funnel
 1
1.23.
 Suction through a glass filter
 1
1.24.
 Washing of precipitates by decantation
 1
1.25.
 Washing of precipitates on a filter
 2
1.26.
 Drying of precipitates on a filter with appropriate solvents
 2
1.27.
 Recrystallization of substances from aqueous solution
 1
1.28.
 Recrystallization of substances from a known organic solvent
 2
1.29.
 Practical choice of an appropriate solvent for recrystallization of a substance
 3
1.30.
 Drying of substances in a drying box
 2
1.31.
 Drying of substances in a desiccator
 2
1.32.
 Connecting and using of a gas washing bottle
 2
1.33.
 Extraction with an inmiscible solvent
 1



2. Identification of inorganic and organic compounds:
general principles
2.1.
 Test-tube reactions
 1
2.2.
 Technique of reactions performed in a dot dish and on a filter paper
 1
2.3.
 Group reactions of some cations and anions specified by the organizer
 2
2.4.
 Selective reactions of some cations and anions specified by the organizer
 2
2.5.
 Specific reactions of some cations and anions specified by the organizer
 3
2.6.
 Identification of elements by flame coloration (using a platinum wire/MgO rod, Co-glass)
 2
2.7.
 Using a hand spectroscope/Bunsen spectroscope
 3
2.8.
 Melting point determination with Kofler or similar type of apparatus
 3
2.9.
 Qualitative evidence of basic functional groups of organic substances specified by the organizer
 2
2.10.
 Exploitation of some specific reactions for identification of organic compounds (specified by the organizer)
 3



3. Determination of some inorganic and organic compounds:
general principles
3.1.
 Quantitative determinations using precipitation reactions
 2
3.2.
 Igniting of a precipitate in a crucible
 1
3.3.
 Quantitative volumetric determinations
 1
3.4.
 Rules at titrating
 1
3.5.
 Use of a pipetting ball
 1
3.6.
 Preparation of a standard solution
 2
3.7.
 Alkalimetric and acidimetric determinations
 2
3.8.
 Color transitions of indicators at alkalimetric and acidimetric determinations
 2
3.9.
 Direct and indirect determinations (back titration)
 3
3.10.
 Manganometric determinations
 3
3.11.
 Iodometric determinations
 3
3.12.
 Other types of determinations on basis of redox reactions
 3
3.13.
 Complexometric determinations
 3
3.14.
 Color transitions of solutions at complexometric determinations
 3
3.15.
 Volumetric determinations on basis of precipitation reactions
 3
3.16.
 Thermometric titration
 3



4. Special measurements and procedures
4.1.
 Measuring with a pH-meter
 2
4.2.
 Chromatography on thin layers
 3
4.3.
 Column chromatography
 3
4.4.
 Separation on ion exchanger
 3
4.5.
 Measuring of UV-VIS absorbances with a spectral photometer
 3
4.6.
 Performing of conductivity measurements
 3



5. Evaluation of results
5.1.
 Estimation of experimental errors (significant figures, plots scales)
 1



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