International Chemistry Olympiad

IChO 1973

Sofia, Bulgaria · 6 theory problems with complete solutions

  1. Problem 1: Nitration product of a hydroxybenzene and its electroreduction

    In nitrating a hydroxy derivative of benzene a compound is formed which contains 49.0 % by mass of oxygen. A charge of 4350 C is required for a total electroreduction of 0.458 g of the compound, efficiency being 80 %.

    Problem:

    1.1 Determine the stoichiometric as well as structural formulas of the compound if the product of the electrochemical reduction is an aromatic hydroxy amino derivative.

    F (Faraday's charge) = \(96\,500\ \mathrm{C\,mol^{-1}}\)

    Official English text of the problem.

  2. Problem 2: Combustion of a gaseous hydrocarbon in a closed vessel

    A mixture of a gaseous hydrocarbon and oxygen is in a vessel of a volume of 1 dm³ at a temperature of 406.5 K and a pressure of 101 325 Pa. There is twice as much oxygen in the mixture as is needed for the reaction with the hydrocarbon. After combustion of the hydrocarbon the pressure in the vessel (at the same temperature) is increased by 5 %.

    Problem:

    2.1 What hydrocarbon was in the mixture when the mass of water formed by the combustion was 0.162 g.

    Official English text of the problem.

  3. Problem 3: Ionisation of acetic and hypochlorous acids in a mixture

    Equal volumes (\(10\ \mathrm{cm^3}\)) of 0.01-molar solutions of \(\ce{CH3COOH}\) and \(\ce{HClO}\) were mixed and then diluted to a total volume of \(100\ \mathrm{cm^3}\). Ionisation constant of \(\ce{CH3COOH}\) is equal to \(1.8\times10^{-5}\) and that for \(\ce{HClO}\) is \(3{,}7\times10^{-8}\).

    Problems:

    Calculate:

    3.1 degree of ionisation for each of the acids in the solution,

    3.2 degree of ionisation of \(\ce{HClO}\) if the diluted solution would not contain \(\ce{CH3COOH}\),

    3.3 pH value for the solution containing at the same time \(\ce{CH3COOH}\) and \(\ce{HClO}\).

    Official English text of the problem.

  4. Problem 4: Precipitate and dry residue from two unknown solutions

    When solutions of two unknown substances are mixed together in stoichiometric ratio, 1.25 g of a precipitate are formed which contain a salt of a bivalent metal \(\ce{M}\). The precipitate when heated to 1100 °C is decomposed to 0.70 g of a solid metal oxide \(\ce{MO}\) and another gaseous oxide. After evaporation of the filtrate, a dry residue with a mass of 2.0 g remains which yields two products by thermal decomposition at 215 °C: a gaseous oxide and 0.90 g of water vapour. The total volume of the gaseous mixture is 1.68 dm³ (at STP).

    Problem:

    4.1 Determine the unknown compounds and write chemical equations for the above mentioned reactions.

    Official English text of the problem.

  5. Problem 5: Shortest syntheses of ethyl benzoate and aminobenzoic acids

    Using your knowledge about the properties of benzene and its derivatives, write chemical equations for reactions by which ethyl ester of benzoic acid as well as o-, m-, and p-amino benzoic acids are prepared in the shortest way.

    Official English text of the problem.

  6. Problem 6: Hydration of a mixture of two homologous hydrocarbons

    A gaseous mixture containing two neighbour hydrocarbons of the same homologous series was 14.4 times as dense as hydrogen. This mixture with a volume of 16.8 dm³ was hydrated and 350 g of the solution were obtained when the products of hydration were absorbed in water. Ten grams of this solution were taken and heated in the presence of silver(I) oxide which was prepared from 70 cm³ of a 1 N silver(I) nitrate solution. Unreacted \(\ce{Ag2O}\) was dissolved in an aqueous ammonia solution and a residual precipitate was filtered off. The filtrate was acidified with nitric acid and addition of an excess of sodium bromide to it resulted in 9.4 g of a precipitate.

    When the mixture of the hydrocarbons that remained unreacted, was mixed with a 50 % excess of hydrogen and transmitted above a heated Pt-catalyst, its resulting volume decreased to 11.2 dm³. Volumes of gases were measured in STP conditions.

    Problems:

    6.1 What hydrocarbons were in the starting mixture?

    6.2 Write chemical equations for the above mentioned reactions.

    6.3 Calculate the composition of the starting mixture in % by volume.

    6.4 How much (in %) of each hydrocarbon was hydrated?

    Official English text of the problem.