# Wednesday 13 June 2012 Morning

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2 2 Answer all the questions. 1 Nitrogen monoxide is formed when nitrogen and oxygen from the air combine. N 2 (g) + 2 (g) 2N(g) equation 1.1 Under normal atmospheric conditions, a further reaction occurs in the air to form N 2. 2N(g) + 2 (g) 2N 2 (g) equation 1.2 These reactions have both advantages and disadvantages for the environment. (a) Give the oxidation states of nitrogen in: N 2... N... [2] Give the systematic name of N 2. (b) Describe what you would expect to see when the reaction in equation 1.2 occurs.... [1] (c) Give one advantage and one disadvantage to the environment of the formation of N 2 from N 2 in an industrial process. advantage disadvantage [2]

3 (d) The overall equation for the formation of N 2 (g) is given below. 3 N 2 (g) (g) 2N 2 (g) ΔH = +66 kj mol 1 equation 1.3 At room temperature and pressure: Show that the concentration of oxygen in air is mol dm 3. Calculate the concentration of nitrogen in air. Assume that air consists of nitrogen and oxygen in the mole ratio 4.0 : 1.0 and that one mole of gas occupies 24 dm 3 at room temperature and pressure. [N 2 ] =... mol dm 3 [2] Write the expression for the equilibrium constant, K c, for the reaction shown in equation 1.3. K c = [1] (iii) Use the concentrations of N 2 and 2 from to work out the equilibrium concentration of N 2 in air at room temperature and pressure. K c = dm 3 mol 1 at room temperature for equation 1.3. Give your answer to an appropriate number of significant figures. [N 2 ] =... mol dm 3 [3] Turn over

4 4 N 2 (g) (g) 2N 2 (g) ΔH = +66 kj mol 1 equation 1.3 (iv) How would the value of the equilibrium constant for the equilibrium shown in equation 1.3 change, if at all, if the temperature were raised to 1500 K? Give reasons for your answer.... [3] (v) The pressure was increased to 100 atmospheres, keeping the temperature at room temperature. What effect would this have on the equilibrium position for equation 1.3? Give a reason for your answer.... [2] (e) N 2 can be oxidised to form nitric(v) acid, HN 3. Nitric(V) acid is a strong acid in aqueous solution. Write an equation for the ionisation of nitric(v) acid in water. [2] Calculate the ph of a mol dm 3 solution of nitric(v) acid. ph =... [2]

5 (f) 5 When concentrated nitric(v) acid reacts with concentrated sulfuric(vi) acid, each sulfuric(vi) acid molecule donates one proton to a nitric(v) acid molecule. The ion formed from nitric(v) acid breaks down to form water and another positive ion. Suggest an equation for the overall reaction of sulfuric(vi) acid with nitric(v) acid. [2] Suggest the name of the conjugate base of sulfuric(vi) acid that is formed in the overall reaction in. (iii) Give a laboratory use for the solution formed in the reaction described in. [Total: 25] Turn over

6 6 2 The malolactic fermentation is a reaction that occurs when wine is matured before being bottled. The process results in the wine tasting smoother and less acidic. H + compound X malic acid lactic acid C 3 H 6 3 (a) Name compound X. Give the systematic name for lactic acid. (b) The lactic acid molecule has one chiral centre. Draw diagrams that show the two stereoisomers of lactic acid and how they are related. [2] Give the number of chiral centres in a malic acid molecule.

7 (c) The following data are available for the two acids. 7 pk a malic acid 3.40 and 5.13 lactic acid 3.86 Suggest why two pk a values are given for malic acid. Use the pk a data to suggest why lactic acid produces a smoother, less acidic wine than malic acid.... [2] (d) Write an equation to represent the equilibrium that occurs when lactic acid dissolves in water. Represent lactic acid as C 3 H 6 3. [1] The pk a for lactic acid is Show that the value of K a is mol dm 3. [1] (iii) Calculate the ph of a 0.10 mol dm 3 solution of lactic acid. ph =... [2] (iv) A wine has a ph of 3.0. Calculate the ratio [salt]/[acid] for lactic acid at this ph. (K a = mol dm 3 ) ratio [salt]/[acid] =... [2] Turn over

8 8 H malic acid lactic acid (e) When reacted with sulfuric acid, lactic acid, C 3 H 6 3, loses water to form a compound with the molecular formula C 6 H 8 4. The infrared spectrum of this compound shows an absorption at cm 1 and no absorptions above 3000 cm 1. Suggest a structure for this compound, giving your reasoning [3] (f) When malic acid is heated, it loses water to form an acid anhydride with the molecular formula C 4 H 2 3. Suggest a structure for this compound. [2]

9 (g) You may need to refer to the list of reactions in the Data Sheet in answering this part. Lactic acid can be made in the laboratory using the following two-stage synthesis. 9 stage 1 compound Y stage 2 compound A lactic acid Name compound A. Draw the structure of compound Y. [1] (iii) Underline two words in the following list that describe the mechanism of the reaction in stage 1. addition electrophilic elimination nucleophilic radical substitution [2] (iv) Suggest the other product of stage 2, apart from lactic acid.... [2] Turn over

10 10 stage 1 compound Y stage 2 compound A lactic acid (h) A student suggests that a test to distinguish between compound A and lactic acid would be to heat a sample of each with acidified potassium dichromate(vi). Describe the colour change that compound A would give with this reagent and give the formula of the organic product. colour change from... to... organic product [2] Explain why the test will not distinguish lactic acid from compound A.... [2] [Total: 29]

11 11 3 In 2006, a green synthesis method was developed for converting glycerin into propylene glycol. The new process involved the use of a transition metal catalyst. Propylene glycol has many uses, including as an antifreeze. The overall reaction is shown below. CH 2 CH 2 + CH 2 CH 3 + equation 3.1 glycerin propylene glycol (a) Give the systematic name for propylene glycol.... [1] (b) Glycerin is a co-product in the manufacture of biodiesel from vegetable oil. Explain what is meant by the term co-product, distinguishing it from by-product.... [2] Name the type of reaction by which glycerin can be obtained directly from vegetable oil. (c) Suggest one reason why the synthesis in equation 3.1 is described as green [1] (d) The reaction in equation 3.1 was carried out with the reactants and products in the gas phase under high pressure. Suggest and explain a reason for the use of a high pressure in this reaction [2] Turn over

12 12 (e) A possible mechanism for the reaction in equation 3.1 is shown below. The mechanism is incomplete. H H H H H H CH 2 C H 2 step 1 H 2 CH 2 C H 3 step 2 + H 2 CH 2 CH H 3 H glycerin acetol propylene glycol Draw another curly arrow on the glycerin molecule to complete the electron movements involved in step 1. [1] Step 1 involves the dehydration of glycerin. Give another name for this type of reaction. (iii) Name the functional groups in acetol.... [2] (iv) When the reaction is carried out under the same conditions but in the absence of hydrogen, acetol is formed as the end product. Describe and explain how acetol can be distinguished from glycerin using both infrared and NMR spectroscopy. Describe and explain the splitting (if any) of each of the peaks in the NMR spectrum of acetol. In your answer you should indicate how the spectroscopic peaks you predict are linked to the structure of the compound.... [6]

13 13 CH 2 CH 2 + CH 2 CH 3 + equation 3.1 glycerin propylene glycol (f) The catalyst for the reaction in equation 3.1 is copper(ii) chromite, Cu 2 Cr 2 5. Give the oxidation state of chromium in this compound. Give with a reason, the effect, if any, of the presence of the catalyst on the equilibrium constant of the reaction in equation [2] (g) In a small-scale experiment, 15 g of glycerin, C 3 H 8 3, were treated with excess hydrogen. 9.0 g of propylene glycol, C 3 H 8 2, were formed. Calculate the percentage yield of the reaction. % yield =... % [2] [Total: 22] Turn over

14 4 Ionic liquids are now often used as solvents for Friedel Crafts acylation reactions. These reactions now generate much less toxic waste than the old process. 14 (a) Complete the equation for a Friedel Crafts acylation of benzene. Give the full structural formula of the group attached to the benzene ring. + H 3 Cl [2] Give the systematic name of CH 3 CCl. (iii) Give two words that describe the type of mechanism of the reaction described in.... [2] (b) In the old process for Friedel Crafts reactions, aluminium chloride is used as the catalyst. The products of these reactions cannot be recycled because they could easily cause contamination of the environment. Suggest one way in which the products of the old process might contaminate the environment [1] (c) Ionic liquids have large cations and anions, such as those shown in the table below. Complete the table below for the two ions. ion number of electron pairs around central atom shape of ion bond angle around central atom / (C 2 H 5 ) 4 N + PF 6 [4]

15 15 Suggest why salts consisting of large cations and large anions have low melting points.... [2] (d) Friedel Crafts reactions can be used to identify the presence of an aromatic ring in an organic compound. Benzene, for example, reacts with compound Z and aluminium chloride to form triphenylmethane. Many triphenylmethane derivatives are coloured. H C Suggest the formula of compound Z. triphenylmethane [1] Explain why dyes absorb visible light (and thus appear coloured) whereas benzene absorbs ultraviolet light and appears colourless. In your answer you should show how the points you make link together.... [6] Turn over

16 16 (e) The Kekulé model of benzene shown below does not explain the bromination reaction of benzene. Predict a product of the bromination of the Kekulé structure. Compare this product with the actual product formed when bromine reacts with benzene (in the presence of an iron catalyst). Explain why benzene reacts as it does. In your answer you should use appropriate technical terms spelled correctly [5] [Total: 24]

17 17 5 Zinc chloride, ZnCl 2, is used as a flux for soldering as it removes the oxide coating of the metal being soldered, exposing the bare metal surface. (a) Complete the electron configuration for a zinc atom. 1s 2 2s 2 2p 6 3s 2 3p 6 [1] (b) Zinc forms exclusively 2+ ions. Its third ionisation enthalpy is much higher than the first and second ionisation enthalpies. Write the equation corresponding to the third ionisation enthalpy of zinc. Show state symbols. [1] Suggest, in terms of electron configurations, why zinc forms only 2+ ions. (iii) Give the formula of zinc sulfate(vi). (c) When hydrated zinc chloride is heated, HCl is formed and this helps the zinc chloride to function as a flux. Hydrated zinc chloride has the formula ZnCl 2 2H 2 where two moles of water are included in the lattice with one mole of ZnCl 2. Suggest an equation for the decomposition of one mole of ZnCl 2 2H 2 to give one mole of HCl. [1] Turn over

18 18 (d) Anhydrous zinc chloride is very soluble in water. An energy level diagram for the dissolving process is shown. Zn 2+ (g) + 2Cl (g) enthalpy 2734 kj mol 1 ZnCl 2 (s) ZnCl 2 (aq) What name is given t o the enthalpy change which has the value 2734 kj mol 1? The enthalpy changes of hydration of the ions are: Zn kj mol 1 Cl 363 kj mol 1 Calculate a value for the enthalpy change of solution, ΔH soln, of ZnCl 2. ΔH soln ZnCl 2 =... kj mol 1 [3] (iii) List the bonds that are broken and made when an ionic substance dissolves in water. broken... made [3]

19 (e) Many ionic substances dissolve in water with a positive value for ΔS sys. 19 However, when the salt consists of small highly charged ions (for example, Ca 2+ ), ΔS sys has a negative value. Give the meaning of the term entropy. Suggest why ΔS sys is often positive for dissolving processes but negative for the dissolving of some calcium salts [4] (f) A particular salt has an endothermic enthalpy change of solution. State how the solubility of this salt would change, if at all, as temperature is increased. Explain your answer in terms of entropy changes [4] [Total: 20] END F QUESTIN PAPER

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