9701_m18_qp_42
A paper of Chemistry, 9701
Questions:
9
Year:
2018
Paper:
4
Variant:
2

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Hydrogen cyanide, HCN, is a weak acid in aqueous solution. HCNH++ CN–Ka = 6.2 × 10–10 mol dm–3 Calculate the pH of 0.10 mol dm–3 HCN.  pH = Draw a ‘dot-and-cross’ diagram to represent the bonding in the hydrogencyanide molecule. Show the outer shell electrons only.  State the hybridisation of the carbon and nitrogen atoms in hydrogencyanide, and give the H–C–N bond angle. hybridisation of C hybridisation of N H–C–N bond angle  Suggest structures for the organic products A and B in the following reactions. Assume that HCN reacts in a similar way to RCN. HCN H2 + Ni heat with HCl A B  Adding a measured quantity of KCN to a solution of NiCl 2 produces the complex [Ni(CN)2Cl 2]x. Deduce the overall charge, x, on this complex.  x = The complex can exist as two separate isomers with the same geometry around the nickel ion. State the type of isomerism shown by these isomers. If bromide ions are present in the solution, the complex [Ni(CN)2Cl Br]x can form. Assuming that [Ni(CN)2Cl Br]x has the same geometry as [Ni(CN)2Cl 2]x, state the number of isomers of [Ni(CN)2Cl Br]x that could exist, and draw their structures in the box. ● number of isomers of [Ni(CN)2Cl Br]x structures of the isomers of [Ni(CN)2Cl Br]x  An aqueous solution of KCN is gradually added to a solution of NiSO4 until the KCN is in excess. The following series of reactions takes place. NiSO4 more KCN KCN C green precipitate D yellow solution E red solution KCN in excess ● ● The oxidation state of nickel does not change during these reactions. ● ● None of C, D or E contains sulfur. ● ● C contains no potassium. ● ● The K : Ni ratio in D is 2 : 1. ● ● The K : Ni ratio in E is 3 : 1. Use the information to suggest the formulae of C, D and E. C D E  
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Complete the equations to show the two types of polymerisation. Draw one repeat unit for each polymer. Include any other products. ● addition polymerisation n CH2=CHCH3● condensation polymerisation n HO2CCH2CO2H+ n HOCH2CH2OH Suggest the sign of the entropy changes, ΔS o, for each of the two types of polymerisation. Explain your answers. ● ΔS o for addition polymerisation ● ΔS o for condensation polymerisation  An amide bond forms when a carboxylic acid reacts with an amine. Complete the equation by writing the products in the box. R–CO2H + H2N–R' +  Use your answer to to work out the bonds that are broken and the bonds that are formed during the reaction between a carboxylic acid and an amine. ● ● bonds that are broken ● ● bonds that are formed  Use bond energy values from the Data Booklet to calculate the enthalpy change, ΔH o, when one mole of amide bonds is formed in the reaction in . ΔH o = kJ Amide bonds can also be formed by reacting acyl chlorides with amines. The enthalpy change for this process, ΔH o, is – 6.00 kJ mol–1. Calculate the minimum entropy change, ΔS o, for this reaction to be spontaneous at 298 K. ΔS o = J K–1 mol–1 The repeat unit of the polyamide Kevlar is shown. O O N H N H The monomers of Kevlar, benzene-1,4-dioic acid and 1,4-diaminobenzene, can be synthesised as follows. H3C CH3 HO2C CO2H benzene-1,4-dioic acid reaction 1 O2N NO2 H2N NH2 1,4-diaminobenzene reaction 2 State the reagents and conditions needed for: reaction 1 reaction 2 Kevlar is both strong and rigid. Complete the table to identify two intermolecular forces and the groups involved which are responsible for these properties of Kevlar. intermolecular force groupinvolved  
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Two molecules of compoundF react together under suitable conditions to form compoundG. Some information about compounds F and G is given. ● ● The mass spectrum of F has a peak due to the molecular ion at m / e=106, and a peak at m / e=107 with an abundance 8% of the 106 peak. ● ● The mass spectrum of G has a peak due to the molecular ion at m / e=212, and major peaks at m / e=91 and m / e=105. ● ● Both F and G contain oxygen and are neutral compounds which are insoluble in water. ● ● The 1H NMR spectrum of F includes a singlet peak at δ=10.0 due to one proton. ● ● The 1H NMR spectrum of G includes a singlet peak at δ=5.1 due to two protons. ● ● When G is heated with dilute sulfuric acid, benzoic acid, C6H5CO2H, and phenylmethanol, C6H5CH2OH, are produced. Use this information to answer – . Explain how the mass spectrum of F shows that a molecule of F contains seven carbon atoms. Show your working.  Suggest the molecular formula of the fragment of G at m / e=91. Suggest the molecular formulae of F and G. F G  Suggest structures for compounds F and G. F G  On the structures you have drawn in , circle the protons responsible for the 1HNMR peaks at δ=10.0 in F and δ=5.1 in G. State the type of reaction that G undergoes when heated with dilute sulfuricacid. Describe and explain the relative acidities of benzoicacid, phenylmethanol and 4-methylphenol. CO2H benzoic acid CH2OH H3C phenylmethanol OH 4-methylphenol The ester 4-methylphenyl benzoate is used in the manufacture of perfumes. O O 4-methylphenyl benzoate H3C Suggest a two-step route for the synthesis of 4-methylphenyl benzoate from 4-methylphenol and benzoicacid. Include reagents and conditions for each step, and the structure of the intermediate compound.