= ‘sis anew secon | ocr* ADVANCED SUBSIDIARY GCE CHEMISTRY A F322 Chains, Energy and Resources Monday 7 June 2010 ‘Morning Duration: hour 46 minutos OY ed steal: or Gromit Arse) te ale Ragu: = =a = = eS re 1+ Wot yeurname lary capa ls, your Cate Nb and Candle Narberin he bons bows ‘Use lack Poel may be sod or raps and agra ony ‘ead each question crfly and mak sire at ou brow whe You Rev do belo staring eur enone to jer sneer exc questo inthe spice prods. tonal pape maybe ved acest at urs clear show your Canale Nant, Carr Number an ureton nanos). INFORMATION FOR CANDIOATES + Therunber of mars is gen ntact [J teen each question or part questn, : ‘Where you se on yu wl be award mas the quay of writenconmuniconn means reap you srk Serta ee at png, putnam aa at aig ‘gai inbaon lary an chee sing speci erably whe appropri ‘Retr aon snow ae spain ay elodsone {Theft nba mr ors paper 00 ‘Tis document cont of 24 pape ry bark pepe we incl L see ety tunove_rT 2 “1 ‘Answer all the questions. 11 The akanos are an homologous sries of hycrocrbons. ‘The tabi showe nlormaton about some sagt chain alkanes. kane | molecular formula | boiling point /C ‘methane on, =164 ‘thane “oH =09 propane oH 2 | butane Cato | (2) () Whatis meant by an homologous series? oy i) Explain wy the boing pont increase down the alkane homologous series. Loosen aio ; A ae eerste noe reapeme ere stec eco tenaes alkyne sty ropyne: buttyne hectyne (Suggest the name ofa staight chain alkyne with the molecular formula CyH (ll) Deduce the goneral formula foran alkyne. 3535 35 335M BS WB HH NIL {ii The alkynes contain the C=C funciona group. ‘Suggest he ceplayed formula for propyne. (@¥)_ Hexct-yne has many cyclic structural isomers. ‘Draw the skeletal structure of one ofthese cyclic structural isomers. a R ® R z R a g a a 3 a a R a a g R ® R R R R R Levene rumor]T ‘ 71 {€)Ettyno is commonly called acetone. IRis used in an oxy-acetylne fame which is hot enough to cut through ste Ettyne completely combusts as shown in the equation below, Galea th the tale below. thay change of combustion of ettyne using the average Bond enthalpies in [bona | average bond enthalpy / ki mot? 45 +87 +98 805 rr enthalpy change of combustion = ks mor" (3) a, RE ETT5 7 (@)Etryne is formed when water reacts with calcium carbide, CaC, Cac) + 24,01) > CalOH),{6) + C,H) ‘The standard enthalpy change ofthis reaction can be determined indirect using standard enthalpy changes of formation. (What ie moant by the torm standard enthalpy change of formation, Hj? You should state the standard conditions in your answer. (i) Standard enthalpy changes of formation are shown in the table below, ‘standard enthalpy chan et ormation, ab smal a0) =60 HoH calor 0) CAG) Calculate the standard enthalpy change ofthe reaction Cage) + 24,01) > CalOH),le) + CHa) standard enthalpy change of reaction = ki mor" [3] — el (OVE R R ® R R R R g R R a R R R R R R & R R g 8 g g g 8 7rT : (©) factory makes ettyne gas from caleium carbide, CaC,. (ne ofthe waste products is calcium hydroxide aC, + 2H,0 > Ca(OH), + O2Hy Each day 1.00 x 108 grams of 5 cium carbide are used and 3.60 x 10° dn of ethyne gas, ‘measured at room temperature and pressure, ls manufactured. (Calculate the atom economy for this process using the relative formula masses in the table below. ‘compound relative formula mass ca eat | HO 760 Calor, TAA OH. 260 ‘atom econam (ll) Calculate the amount, in moles, of CaC, used each day amount of Cac, (li) Calculate the amount, in moles, of CH, made each day. amount of GH, (iv) Calculate the percentage yield of CH, L percentage yield = 1612) mol {1} “0r 7 7 (¥) Comment on the percentage yield and the atom economy ofthis process in terms of sustainably (otal: 23) R z ® ie Ey a a R a a a a 2 3 2 z 2 & & & & & & a a a & R R & a R rane NNN w NAMA B ESASr 2 : 7 Petrol and siese are both complex mixtures of hydrocarbons used as fuels in vansport. {8) Petrol contains some branched chain alkanes. ‘The numberof carbon aloms per molecule varies between five and nine, "Name one branched chain alkane with betwoen five and rine carbon atoms, 1m () When petra! burns in an intemal combustion engine the exhaust gases contain CO,, CO, NO, Nz. Op HO and unburt hydrocarbons. (Wat tft does the adsorption of inrared radiation have onthe bonds in CO, molecules Inthe atmosphere? m (W)_ Why 18 CO presenti the exaust casos? 1 (ii) oth NO and CO are atmospheric pollutants For each pollutant, describe one environmental problem, No. co. a (©) Most ars av fitted wth catalytic convertor which catalyses the exothermic reaction between INO and GO to form two less harmful gases. (0 Name the wo gases formed and write an equation for his reaction. a 9990990000900 900: EsrT ° 7 (NO and CO react vary slowly without a catalyst. ‘The catalyst in a catalytic converter increases the rate of reaction. Explain, using an enthalpy profile diagram and the Boltzmann distribution model, how the use ofa catalyst increases the rate of reacon, 55 35 53533 1 33 BH DS HS Lee aww WM suaBBRA HH:r ” “] (@) Many Iortas and some cars use dosel powered engines. Biodiesel is being developed as a substitute for dese from crud ol Biodiesel is a methyl estr ofa long chain carbonic acid ‘The flow chart shows how itis produced. pants — plant oll -> long chain caborylc acide —> biodiesel Deserbe the benefits and «isadvantages of changing ftom diesel to biodiesel. a (MEA een a ra rerarerrrarrrrererreanaaemsmnaanemmmmcmmmammmmmmmmmaaaaia" BLANK PAGE PLEASE DO NOT WRITE ON THIS PAGE AOE Ar 2 12 Alcohols are used in the industrial production of many organic compounds, (2) Complete the flowchart below to show the organic product formed in each ofthe butan-t-0 cepegmeo nd rohan (CH,CH,CH,CH,OH wesovegenaeg sti 4 (CH,COOH/H,SO, reflux Linens oy OOO OOOL9900RNAmA NOON OOO AGT cpoooooe oe eooooopoO OOO DOEDE EEE OOO OOOO ODD:rT ® 1 (©) Butan-1-l can be prepared by the alkaline hydrolysis of -odobutane i q H a : y a & e g a a & a a & & & g & g & & g e & a (CH,CH,CH,CH, + OH" —> CH,CH,CH,CH,OH + ‘The reaction mire is gently heated for 20 minutes. () The curly arrow model i used in reaction mechanisms to show the movement of electron pats Use the curly arrow model 1o outine the mechanism for the alkaline hycroysis of ‘odebutane, In your answer, include the name ofthe mechanism, the typeof bond fision and rolovant dipoles. ‘name of mechanism type of bond fission 1 (i) A student decides to prepare butan-t-o by the alkaline hydrolysis of -chlorobutane. ‘Suggest, with reasons, any change in the conditions from those used in the alkaline hydrelyie of odobutane a (otat: 11) Lessee rumor 0ABLANK PAGE PLEASE 00 NOT WRITE ONTHIS PAGE [ees wmnun mun 222222929990009000900900909099990909909000000009000000000 9090000000000r 6 7T 4 Infrared spectroscopy and mass spectromety ae used to identity substances. (Police use breathalysors to detect ethanol inthe breath of divers, 0 w wy Levees ‘Some medern breathalysers use infrared spectroscopy. ‘Suggest two charactortc infrarad absorptions that could be used 10 identi the presence of ethanol vapour Benn 2 enw a ‘Some older breathalysers used the redex action between acctodcichromate(V) ons {and ethanol A colour change was eeen which indicated the presence of ethanol the breath ‘Whats the colour change that would be seen in tis breathalyser if ethanol was present in he breath? 0 0 Give an equation to show the reaction between acdtied dichromate(V) lone and than Use 0} 0 represent the acted cichromate(V) ons, the oxidising agont tum over |T 6 7 (©) Intared spectroscopy and mass spectrometry are used inthe search for organic molecules in ‘outer pape Compound A has been analysed by infrared spectroscopy. 100 20. 60 40 20 4000" $500" 3000" "2500" "2000" “is00° i000” 800 wavenumber/on ‘The mass spectrum of compound A is shown below. 10 es relative 60 sbundance C9 20. dl - 8G ae ago 4080 Liven a I & 8 & 8 & & & 8 8 8 FS 8 8 : | ® ® ® i ® & & & & & & & & & & & & & 8 8 e 8 ee 8 8 a 8 & & & %ic ” q (0. A esearch chomist conciudes that compound Aisa hydrocarbon, What evidence is thereto support this conclusion? ea {W) How does the mass spectrum confirm that compound A has @ molecular formula ot Ci? m 3 (i) Draw te structural isomers of Cy a m (0 tdonty th kagmentions hat givers 6 the ftowing peaks inthe mass spectrum. mai8is. rmiz29ie mass oT (¥)_Use your anew to part (i) to idonty which ofthe isomers in part (il) is compound A. Explain your reasoning. 0 (Tota: 19), tunever | ie R i & a & a a a a a a a a a a a a a a a a a a a & a a R R a a R a a & a a a aTr ” T 5 Alkonos B, C,D,E and F are shown below. 4, CHACH, 4, 4. 4 \, / co oc! Ww Hye W \w 8 . ony He, / po W ‘You wit have to refer to these alkenes throughout the question. (0) Deserve, using the erital overlap model, how the x-bond in alkane D is formed. a (©) Many alkenes show E12 isomerism. (Explain why E7Zisomerim is shown in some alkenes, a i) Which two alkenes are a pair of B:Zisomers? (Choose from B, CD, Eand F. PB 1 “4 a 8 8 9 8 8 3 3 2 2 8 6 6 6 8 ® 6 ® 6 o 8 o 8 2 §T » 7 (Describe and explain th reaction of hydrogen bromide, HBr, with alkene B and with alkene D. Include in your answer + equations and structures of the product, + hy one of these allanes gives just one product but the other gives more than one product, + {he reaction mechanism for the reaction wih alkene D using the curly arrow model showing any relevant poles. Your answer neds to be clear and wel organised using appropriate examples from the Chemistry of alkenes B and D. @ Levee tumover OU> i Crow 201 | (6) Alkonos aro a major source of polymers. Alkane B can be polymerisd. (Draw a section of the resultant polymer showing two repeat units m {W) Give the name of tis polymer. nm (9 Poiylethona) is a very unusual polymer because it can cissolve in water under certain ‘conetons OH HOH H (Suggest why polyethenc)) can dissolve in water @ (A) Waste poty(theno) does not cause many environmental problems. (ther polymere euch as polyethens), PVC or PTFE cause signifeant environmental problems. ‘Outing two ways in which waste polymers canbe processedto reduce thei environmental impact @ oooogg ogee ee eeooooocop9DD9 CDC CD OD00a 1 6 An important reaction inthe manufacture of nic acid is th catalytic endation of ammonia, 4NH,(@) + 50,9) = 4NO(G) + 6H,0(G) AH = 909K mor* {() Low pressures and low temperatures woud gve the maximum equtium yield of NO. Explain why. a (©) The actual conditions used in the catalylc oxidation of ammonia include 800°C and an Increase in pressure. ‘Suggest why these conditions are a compromise. a (6) Atactory makes 2.50 x 10° mol of NO a day. (How much energy is released every day? energy released wm (1) Suggest how this energy can be used to reduce the cost of making NO. LL angan naan s22 899595 59HS YS YYS OHSSTr 2 7 7 Compound G was extracted rom the leaves ofa plant. A sample of G was analysed by a research ‘chemist. A summary ofthe chemist’ results shown inthe table type of analysis evidence ‘absorptions at 1080, 1720 and a infrared spectroscopy vety broad absorption at 2600 em percentage composition by mass | C,26.7%:H, 222%: 0, 71.1% (0.00108 mol of G has a mass volumetic analysis co Es Use this information to suggest a possible structure for compound G. BP i em yu ski maa caro ur elnaton ka oe iene La |59535 35353 3 1 8 8 HS HSS SEN BB SNS BISH END OF QUESTION PAPER,PLEASE DO NOT WRITE ON THIS PAGE oooooeo pees ecco ooo ooo opo eo pop oo ooo oe ooo oo ooooopeD EE CCO DO EDO ODO ODC Oem ennn: