Olimpíada Internacional de Química - Principal
Principal
Iniciada em 1968, na Checoslováqia, a International Chemistry Olympiad, IChO, reúne desde então, a cada ano, no mês de julho, aproximadamente 320 estudantes oriundos de 80 diferentes nações. Cada país pode competir com o máximo de 4 estudantes não-universitários, com idade inferior a 20 anos, que submetem a exames teóricos e práticos durante o período do evento (10 dias).
As provas aplicadas são elaboradas por um júri internacional formado por mentores (membros das delegações) e especialistas do país organizador. Ao final do evento, os mais destacados estudantes recebem premios que consistem em medalhas de ouro, prata e bronze. O Brasil iniciou sua participação, com estudantes, neste evento, por ocasião da 31st IChO que se realizou na Tailândia.
As olimpíadas seguintes foram organizadas pelos países: Canadá - 1997, Austrália - 1998, Tailândia - 1999, Dinamarca - 2000, Índia - 2001, Holanda - 2002, Grécia- 2003, Alemanha - 2004, Taiwan - 2005, Coréia (2006), Rússia (2007), Hungria (2008), Inglaterra (2009), Japão (2010), Turquia (2011) e USA (2012), Rússia (2013), Vietnam (2014) e Arzeibajão (2015), Geórgia (2016), Tailândia (2017), República Checa + Eslováqia (2018). As próximas estão programadas para os seguintes países: França (2019), Coreia (2020?), Japão (2021).
Regulamento
(3) Moreover, other countries may apply for the participation in IChO but the organizer has the right to invite the countries only on agreement with the organizers of two forth-coming IChOs. Incoming countries must send observers to two consecutive Olympiads before its pupils can participate in IChO (see also § 3, section 5)..
a) must guarantee the fulfilment of those conditions given in section 2 of this paragraph,
b) must be capable of translating the text of competition tasks from English into the mother tongue of their students and be able to judge the set of tasks and correct the work of the students.
c) have the right to enter a protest which should be addressed to the Chair of the International Jury and, when necessary, ask for solving the problem at the next meeting of the International Jury.
a) the itinerary of the IChO,
b) transportation from/to an airport/station decided by the host country on the day of arrival and departure,
c) the organization of the competition following the regulation,
d) accident insurance for all participants in connection with the organized programme,
e) the opportunity for the mentors to inspect the working room and practical apparatus to be used for the practical tasks before the competition takes place,
f) arrangement for the observance of the safety regulations,
g) the medals, certificates and prizes, which are presented at the official closing ceremony,
h) a printed report on the competition to be distributed not later than six months after the competition.
§5 - Financing
a) is in charge of the actual competition and its supervision according to the regulations,
b) discusses in advance the competition tasks presented by the organizer, their solutions and the marking guidelines, gives com-ments and decides in case of changes,
c) supervises the marking of the examination papers and guarantees that all participants are judged by equal criteria,
d) determines the winners and decides on prizes and documents for the competitors,
e) monitors the competition and suggests changes to the regulations, organization and contents for future IChOs,
f) takes decisions on excluding of a participant or a whole team from the.competition (see also § 11, section 7),
g) elects members of the Steering Committee of the IChO,
h) may form working groups to solve specific chemistry related problems of the IChO.
a) are obliged to maintain a professional discretion about any relevant information they receive during the IChO and must not assist any participants,
b) keep the marking and results secret until proclaimed by the International Jury.
Americas, 1 from Pacific Rim), to serve a two year term. Members are elected for no more than two consecutive terms. Moreover, 1 - 3 members may be selected by the Steering Com-mittee for their particular expertise for periods of one year.
immediate future IChO.
a) calls and chairs the meetings of the Steering Committee.
b) calls and chairs the business meetings of the International Jury dealing with general problems of future International Chemistry Olympiads.
c) has the right to call a special meeting of the International Jury when necessary for some exceptional reasons..
a) provides organizational oversight for the International Chemistry Olympiad,
b) proposes items for consideration at the International Jury sessions.
the IChOs from the very beginning of the Olympiad to the present. The seat of the Office is in Bratislava, Slovakia.
C o m p e t i t i o n
set of preparatory problems from each field. Subjects assigned to level 3 can be classified as level 2 if sufficient background is included in the formulation of the problem (e. g. formulas, graphs, structures, equations)..(4) The organizer cannot set an experimental competition task with an experimental technique of level 3 (Appendix D) without mentioning it at least in one of experimental preparatory tasks.
Appendix B for definitions of these categories).
a) Appendix A 1: Safety Rules for Students in the laboratory.
b) Appendix A 2: Safety Rules and Recommendations for the Host Country of the IChO.
c) Appendix B contains: B 1: Hazard Warning Symbols and Hazard
Designations and their explanation. B 2: R-Ratings and S-Provisions: Nature of special risks (R) and safety advice (S)..
They propose the methods of solution and the marking scheme.
should be present during the discussion.
a) The experimental part must contain at least two independent tasks.
b) No part of the grade can subjectively be evaluated by the staff.
c) Competitors must receive the same substances when solving the tasks from qualitative analytical chemistry.
d) When solving tasks from quantitative analytical chemistry competitors must receive the same substances but with different concentrations.
e) In evaluating the quantitative tasks the master values must not be based on average results of the competitors.
f) The great majority of the grade in quantitative tasks must be given to the mean value as reported by the competitors while some marks may also be given to the corresponding equations, calculations, or explanations directly related to the work. Points must not be awarded for reproducibility.
(1) A maximum of 60 points is allocated to the theoretical tasks and 40 points to the practical tasks, making a total of 100 points.
students' total results before the closing awards' ceremony.
competitors. The exact number of medals is decided on the basis of an anonymous review of the results.
approved in Oslo (Norway) in 1994.
Programa
INTERNATIONAL CHEMISTRY OLYMPIAD
PROGRAM
Level 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.
Theoretical part
1. The atom |
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1.1. |
Introduction |
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1.1.1. |
Counting of nucleons |
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1.1.2. |
Isotopes |
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1.2. |
The hydrogen atom |
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1.2.1. |
Concept of energy levels |
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1.2.2. |
Shape of s-orbitals |
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1.2.3. |
Shape and orientation of p-orbitals |
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1.2.4. |
Shape and orientation of d-orbitals |
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1.2.5. |
Understanding the simplest Schrodinger equation |
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1.2.6. |
Square of the wave function and probability |
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1.2.7. |
Quantum numbers (n, l, ml) |
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1.3. |
Radioactivity |
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1.3.1. |
Types of radioactivity |
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1.3.2. |
Radioactive decay |
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1.3.3. |
Nuclear reactions |
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2. Chemical bonding |
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2.1. |
VSEPR – Simple molecular structures with |
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2.1.1. |
no more than four electron pairs about central atom |
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2.1.2. |
with central atom exceeding the “octet rule” |
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2.2. |
Delocalization and resonance |
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2.3. |
Hybrid orbital theory |
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2.4. |
Molecular orbital theory |
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2.4.1. |
molecular orbital diagram (H2 molecule) |
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2.4.2. |
molecular orbital diagram (N2 and O2 molecules) |
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2.4.3. |
bond orders in O2, O2–, O2+ |
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2.4.4. |
unpaired electrons and paramagnetism |
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3. Chemical calculations |
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3.1.1. |
Balancing equations |
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3.1.2. |
Stoichiometric calculations |
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3.1.3. |
Mass and volume relations (including density) |
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3.1.4. |
Empirical formula |
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3.1.5. |
Avogadro’s number |
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3.1.6. |
Concentration calculations |
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4. Periodic trends |
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4.1. |
Electron configuration |
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4.1.1. |
Pauli exclusion principle |
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4.1.2. |
Hund’s Rule |
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4.1.3. |
Main group elements |
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4.1.4. |
Transition metal elements |
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4.1.5. |
Lanthanide and actinide metals |
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4.2. |
Electronegativity |
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4.3. |
Electron affinity |
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4.4. |
First ionization energy |
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4.5. |
Atomic size |
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4.6. |
Ion size |
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4.7. |
Highest oxidation number |
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5. Inorganic Chemistry |
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5.1. |
Introduction |
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5.1.1. |
Trends in physical properties of elements (Main groups) |
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5.1.1.1. |
melting point |
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5.1.1.2. |
boiling point |
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5.1.1.3. |
metal character |
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5.1.1.4. |
magnetic properties |
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5.1.1.5. |
electrical conductivity |
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5.1.2. |
Oxidation number |
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5.1.3. |
Nomenclature |
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5.1.3.1. |
main group compounds |
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5.1.3.2. |
transition metal compounds |
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5.1.3.3. |
simple metal complexes |
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5.2. |
Groups 1 and 2 |
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5.2.1. |
Trend in reactivity of (heavy elements more reactive) |
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5.2.2. |
Products of reaction with |
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5.2.2.1. |
water |
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5.2.2.2. |
halogens |
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5.2.2.3. |
oxygen |
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5.2.3. |
Basicity of oxides |
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5.2.4. |
Properties of hydrides |
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5.2.5. |
Other compounds, properties and oxidation states |
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5.3. |
Groups 13 – 18 and Hydrogen |
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5.3.1. |
Binary molecular compounds of hydrogen |
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5.3.1.1. |
Formulae |
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5.3.1.2. |
Acid-base properties of CH4, NH3, H2O, H2S |
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5.3.1.3. |
Other properties |
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5.3.2. |
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Group 13 |
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5.3.2.1 |
The oxidation state of boron and aluminium in their oxides and chlorides is +3 |
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5.3.2.2. |
The acid-base properties of aluminium oxide/hydroxide |
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5.3.2.3. |
Reaction of boron(III) oxide with water |
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5.3.2.4. |
Reaction of boron(III) chloride with water |
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5.3.2.5. |
Other compounds, properties and oxidation states |
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5.3.3. |
Group 14 |
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5.3.3.1. |
The oxidation state of Si in its chloride and oxide is +4 |
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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 |
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5.3.3.3. |
Other compounds, properties and oxidation states |
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5.3.4. |
Group 15 |
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5.3.4.1. |
Phosphorus(+5) oxide and chloride, and their reaction with water |
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5.3.4.2. |
Phosphorus(+3) oxide and chloride, and their reaction with water |
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5.3.4.3. |
Oxides of nitrogen |
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a. Reaction of NO to form NO2 |
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b. Dimerization of NO2 |
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c. Reaction of NO2 with water |
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5.3.4.4. |
Redox properties of |
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a. HNO3 and nitrates |
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b. HNO2 and NH2NH2 |
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5.3.4.5. |
Bi(+5) and Bi(+3) |
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5.3.4.6. |
Other compounds, properties and oxidation states |
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5.3.5. |
Group 16 |
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5.3.5.1. |
The +4 and +6 oxidation states of sulfur, reaction of their oxides with water, properties of their acids |
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5.3.5.2. |
Reaction of thiosulfate anion with I2 |
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5.3.5.3. |
Other compounds, properties and oxidation states |
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5.3.6. |
Group 17 (Halogens) |
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5.3.6.1. |
Reactivity and oxidant strength decreases from F2 to I2 |
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5.3.6.2. |
Acid-base properties of the hydrogen halides |
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5.3.6.3. |
The oxidation state of fluorine in its compounds is –1 |
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5.3.6.4. |
The –1, +1, +3, +5, +7 oxidation states of chlorine |
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5.3.6.5. |
Mononuclear oxoanions of chlorine |
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5.3.6.6. |
Reactions of halogens with water |
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5.3.6.7. |
Reaction of Cl2O and Cl2O7 with water |
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5.3.6.8. |
Other compounds, properties and oxidation states |
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5.3.7. |
Group 18 |
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5.4. |
Transition elements |
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5.4.1. |
Common oxidation states of common transition metals: |
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5.4.2. |
Colours of ions listed above in aqueous solution |
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5.4.3. |
Insolubility of Ag, Hg and Cu in HCl |
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5.4.4. |
M2+ arising by dissolution of the other metals in HCl |
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5.4.5. |
Cr(OH)3 and Zn(OH)2 are amphoteric and the other +2 |
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5.4.6. |
MnO4– and Cr2O72– are strong oxidants in acid solution |
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5.4.7. |
pH dependence of products of MnO4– acting as oxidant |
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5.4.8. |
Interconversion between CrO42– and Cr2O72– |
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5.4.9. |
Other compounds, properties and oxidation states |
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5.5. |
Lanthanides and actinides |
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5.6. |
Coordination chemistry including stereochemistry |
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5.6.1. |
Definition of coordination number |
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5.6.2. |
Writing equations for complexation reactions given all formulae |
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5.6.3. |
Formulae of common complex ions |
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5.6.3.1. |
Ag(NH3)2+ |
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5.6.3.2. |
Ag(S2O3)23– |
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5.6.3.3. |
FeSCN2+ |
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5.6.3.4. |
Cu(NH3)42+ |
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5.6.3.5. |
Other complex ions |
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5.6.4. |
(6.5) Ligand field theory (eg and t2g terms, high and low spin) |
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5.6.5. |
Stereochemistry |
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5.6.5.1. |
(6.7) cis and trans |
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5.6.5.2. |
enantiomers |
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5.7. |
Selected industrial processes |
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5.7.1. |
Preparation of H2SO4 |
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5.7.2. |
Preparation of NH3 |
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5.7.3. |
Preparation of Na2CO3 |
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5.7.4. |
Preparation of Cl2 and NaOH |
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5.7.5. |
Preparation of HNO3 |
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6. Physical chemistry |
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6.1. |
Gases |
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6.1.1. |
Ideal gas law |
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6.1.2. |
van der Waal’s gas law |
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6.1.3. |
definition of partial pressure |
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6.1.4. |
Dalton’s Law |
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6.2. |
Thermodynamics |
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6.2.1. |
First Law |
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6.2.1.1. |
Concept of system and surroundings |
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6.2.1.2. |
Energy, heat and work |
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6.2.2. |
Enthalpy |
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6.2.2.1. |
Relationship between internal energy and enthalpy |
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6.2.2.2. |
Definition of heat capacity |
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6.2.2.3. |
Difference between Cp and Cv (ideal gas only) |
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6.2.2.4. |
Enthalpy is a state property (Hess’s Law) |
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6.2.2.5. |
Born-Haber cycle for ionic compounds |
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6.2.2.6. |
Use of standard formation enthalpies |
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6.2.2.7. |
Enthalpies of solution and solvation |
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6.2.2.8. |
Bond enthalpies (definition and use) |
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6.2.3. |
Second Law (Entropy and Free Energy) |
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6.2.3.1. |
Entropy definition (dq / T) |
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6.2.3.2. |
Entropy and disorder |
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6.2.3.3. |
Entropy definition (S = k ln W) |
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6.2.3.4. |
Gibbs energy definition (DG = DH – TDS) |
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6.2.3.5. |
Using DG to predict direction of natural change |
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6.2.3.6. |
Relationship between DG° and equilibrium constant K |
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6.3. |
Equilibrium |
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6.3.1. |
Acid-base |
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6.3.1.1. |
Arrhenius definitions of acids and bases |
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6.3.1.2. |
Bronsted-Lowry definitions |
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6.3.1.3. |
Conjugate acids and bases |
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6.3.1.4. |
pH definition |
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6.3.1.5. |
Kw definition |
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6.3.1.6. |
Ka and Kb as a measure of acid and base strength |
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6.3.1.7. |
Acidity or basicity of ions |
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6.3.1.8. |
Calculation of pH from pKa(weak acid) |
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6.3.1.9. |
Calculation of pH of a simple buffer solution |
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6.3.2. |
Gas phase |
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6.3.2.1. |
Equilibrium constant in partial pressures |
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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 |
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11.4.1.2. |
Nomenclature, kinetics, coenzymes, function of ATP |
3 |
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12. Analytical chemistry |
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12.1. |
Titrations |
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12.1.1. |
acid-base |
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12.1.1.1. |
Titration curve; pH (strong and weak acid) |
2 |
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12.1.1.2. |
Choice of indicators for acidimetry |
2 |
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12.1.2. |
Redox titration |
3 |
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12.2. |
Qualitative analysis |
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12.2.1. |
Ions (Inorganic) |
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12.2.1.1. |
Identification of Ag+, Ba2+, Cl–, SO42– |
2 |
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12.2.1.2. |
Identification of other anions and cations |
3 |
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12.2.2. |
Organic functional groups |
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12.2.2.1. |
Lucas reagent (1-, 2-, 3-alcohols) |
3 |
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12.2.2.2. |
Iodoform reaction |
3 |
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12.2.2.3. |
Identification of primary, secondary, tertiary, quarternary amines in the laboratory |
3 |
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12.3. |
Chromatographic methods of separation |
3 |
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Experimental part |
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Level 1: |
is assigned to the basic experimental activities which are supposed to be mastered by competitors very well |
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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 |
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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 |
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If the organizer wants to apply a technique which is not mentioned in the above syllabus, this technique is set to level 3 automatically. |
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1. Synthesis of inorganic and organic compounds |
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1.1. |
Heating with burners and hotplates |
1 |
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1.2. |
Heating of liquids |
1 |
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1.3. |
Handling the work with inflammable substances and materials |
1 |
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1.4. |
Measuring of masses (analytical balance) |
1 |
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1.5. |
Measuring of volumes of liquids (measuring cylinder, pipette, burette) |
1 |
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1.6. |
Preparation of solutions from a solid compound and solvent |
1 |
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1.7. |
Mixing and dilution of solutions |
1 |
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1.8. |
Mixing and stirring of liquids |
1 |
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1.9. |
Using mixer and magnetic stirrer |
2 |
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1.10. |
Using a dropping funnel |
1 |
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1.11. |
Syntheses in flat bottom vessels – general principles |
1 |
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1.12. |
Syntheses in round bottom vessels – general principles |
1 |
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1.13 |
Syntheses in a closed apparatus – general principles |
1 |
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1.14. |
Using microscale equipment for synthesis |
3 |
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1.15. |
Apparatus for heating of reaction mixture under reflux |
2 |
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1.16. |
Apparatus for distillation of liquids at normal pressure |
2 |
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1.17. |
Apparatus for distillation of liquids at reduced pressure |
2 |
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1.18. |
Apparatus for steam distillation |
3 |
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1.19. |
Filtration through flat paper filter |
1 |
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1.20. |
Filtration through a folded paper filter |
1 |
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1.21. |
Handling a water vacuum pump |
1 |
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1.22. |
Filtration through a Büchner funnel |
1 |
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1.23. |
Suction through a glass filter |
1 |
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1.24. |
Washing of precipitates by decantation |
1 |
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1.25. |
Washing of precipitates on a filter |
2 |
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1.26. |
Drying of precipitates on a filter with appropriate solvents |
2 |
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1.27. |
Recrystallization of substances from aqueous solution |
1 |
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1.28. |
Recrystallization of substances from a known organic solvent |
2 |
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1.29. |
Practical choice of an appropriate solvent for recrystallization of a substance |
3 |
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1.30. |
Drying of substances in a drying box |
2 |
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1.31. |
Drying of substances in a desiccator |
2 |
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1.32. |
Connecting and using of a gas washing bottle |
2 |
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1.33. |
Extraction with an inmiscible solvent |
1 |
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2. Identification of inorganic and organic compounds: |
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2.1. |
Test-tube reactions |
1 |
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2.2. |
Technique of reactions performed in a dot dish and on a filter paper |
1 |
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2.3. |
Group reactions of some cations and anions specified by the organizer |
2 |
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2.4. |
Selective reactions of some cations and anions specified by the organizer |
2 |
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2.5. |
Specific reactions of some cations and anions specified by the organizer |
3 |
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2.6. |
Identification of elements by flame coloration (using a platinum wire/MgO rod, Co-glass) |
2 |
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2.7. |
Using a hand spectroscope/Bunsen spectroscope |
3 |
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2.8. |
Melting point determination with Kofler or similar type of apparatus |
3 |
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2.9. |
Qualitative evidence of basic functional groups of organic substances specified by the organizer |
2 |
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2.10. |
Exploitation of some specific reactions for identification of organic compounds (specified by the organizer) |
3 |
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3. Determination of some inorganic and organic compounds: |
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3.1. |
Quantitative determinations using precipitation reactions |
2 |
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3.2. |
Igniting of a precipitate in a crucible |
1 |
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3.3. |
Quantitative volumetric determinations |
1 |
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3.4. |
Rules at titrating |
1 |
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3.5. |
Use of a pipetting ball |
1 |
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3.6. |
Preparation of a standard solution |
2 |
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3.7. |
Alkalimetric and acidimetric determinations |
2 |
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3.8. |
Color transitions of indicators at alkalimetric and acidimetric determinations |
2 |
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3.9. |
Direct and indirect determinations (back titration) |
3 |
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3.10. |
Manganometric determinations |
3 |
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3.11. |
Iodometric determinations |
3 |
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3.12. |
Other types of determinations on basis of redox reactions |
3 |
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3.13. |
Complexometric determinations |
3 |
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3.14. |
Color transitions of solutions at complexometric determinations |
3 |
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3.15. |
Volumetric determinations on basis of precipitation reactions |
3 |
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3.16. |
Thermometric titration |
3 |
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4. Special measurements and procedures |
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4.1. |
Measuring with a pH-meter |
2 |
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4.2. |
Chromatography on thin layers |
3 |
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4.3. |
Column chromatography |
3 |
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4.4. |
Separation on ion exchanger |
3 |
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4.5. |
Measuring of UV-VIS absorbances with a spectral photometer |
3 |
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4.6. |
Performing of conductivity measurements |
3 |
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5. Evaluation of results
|
Exames
1993
- Exames anteriores a 1994Problemas e soluções
1994
- 26th IChO - Oslo, NoruegaExame teórico
- 26th IChO - Oslo, NoruegaExame laboratório
1995
- 27th IChO - Beijing, ChinaExame laboratório
- 27th IChO - Beijing, ChinaExame teórico
1996
- 28th IChO - Moscou, RussiaExame teórico
- 28th IChO - Moscou, RussiaExame laboratório
1997
- 29th IChO - Montreal, CanadáExame Teórico + Exame laboratório
1998
- 30th IChO - Melbourne, AustráliaExame teórico
- 30th IChO - Melbourne, AustráliaExame laboratório
1999
- 31st IChO - Bangkok, TailândiaExame Teórico
- 31st IChO - Bangkok, TailândiaExame laboratório
2000
- 32nd IChO - Copenhagen, DinamarcaExame teórico
- 32nd IChO - Copenhagen, DinamarcaExame laboratório
2001
- 33rd IChO - Mumbai, ÍndiaExame teórico
- 33rd IChO - Mumbai, ÍndiaExame laboratório
2002
- 34th IChO - Groningen, HolandaExame Teórico
- 34th IChO - Groningen, HolandaExame laboratório
2003
- 35th IChO - Atenas, GréciaExame Teórico
- 35th IChO - Atenas, GréciaExame laboratório
2004
- 36th IChO - Kiel, AlemanhaExame teórico
- 36th IChO - Kiel, AlemanhaExame laboratório
2005
- 37th IChO - Taipei, TaiwanExame laboratório
- 37th IChO - Taipei, TaiwanExame teórico
2006
- 38th IChO - Gyeongsan, Coréia do SulExame teórico
- 38th IChO - Gyeongsan, Coréia do SulExame laboratório
2007
- 39th IChO - Moscou, RússiaExame laboratório
- 39th IChO - Moscou, RússiaExame teórico
2008
- 40th IChO - Budapeste, HungriaExame teórico
- 40th IChO - Budapeste, HungriaExame laboratório
- 40th IChO - HungriaProblemas Preparatórios
2009
- 41st IChO - Cambridge, InglaterraExame Teórico
- 41st IChO - Cambridge, InglaterraExame laboratório
2010
- 42nd IChO - Tóquio, JapãoExame teórico
- 42nd IChO - Tóquio, JapãoExame laboratório
2011
- 43rd IChO - Ancara, TurquiaExame teórico
- 43rd IChO - Ancara, TurquiaExame laboratório
2012
- 44th IChO - Washington, USAExame Teórico
- 44th IChO - Washington, USAExame laboratório
2013
- 45th IChO - Moscou, RússiaExame teórico
- 45th IChO - Moscou, RússiaExame laboratório
2014
- 46th IChO - Hanói, VietnamExame teórico
- 46th IChO - Hanói, VietnamExame laboratório
2015
- 47th IChO - Baku, AzerbaijãoProblemas preparatórios
- 47th IChO - Baku, AzerbaijãoExame teórico
- 47th IChO - Baku, AzerbaijãoExame laboratório
2016
- 48th IChO - Tbilisi, GeórgiaExame laboratório
- 48th IChO - Tbilisi, GeórgiaExame teórico
- 48th IChO - Tbilisi, GeórgiaProblemas preparatórios
2017
- 49th IChO - Nakhon Pathom, TailândiaProblemas preparatórios
- 49th IChO - Nakhon Pathom, TailândiaExame Teórico
- 49th IChO - Nakhon Pathom, TailândiaExame Laboratório
Resultados
ee
Coordenadorias
ss