“Model | AQA2 Answers | Pease wite clearly in block capitals a — Sumame Forename(s) Candiate signature A-level CHEMISTRY Paper 2 Organic and Physical Chemistry Monday 19 June 2017 Morning Time allowed: 2 hours Materials For this paper you must have ForBeaines ie + the Periodic Table/Data Booklet, provided as an insert (enclosed) Question | Mat + a ruler with millimetre measurements ‘+ a calor, which you are expected to use where appropriate, Instructions + Use Black nk or black ball point pan. «+ Flin the boxes atthe op of tis page. + Do all rough work inthis bone. Croes through any work you do not ‘want tae marked Information + The marks for questions are shown in brackets, ‘The maimum mark for his paper is 105 aman 7405/27 | Anawer all questions in he spaces provided Figure 1 shows some compounds made from a halogenoakane, Figure + Reacon t Rescion2 Compounds «FEES caycscraor SEE cHycHecHate | Rescon 8 | Cat [11] raw he displayed formula of compound J How OH (1 mara, ' t + Cost Fonet the 0-4 4~C-C-C-O-H boowd. wou |[BT7]-[2] Name te mechanism for Reacton 2 and give an essential condition used to ‘ensure thet CH.CH,CH.NH, is tho major product. [2 marks] Name of necharsm _Nucleophilic Sebstihsion ok is 4s OS GF coiten Grease Nil + Ses aT Calculate the mass, in grams, of CH,CHCH:NHs produced from 25.2.9 of CCH.CH,CH.Br in Reaction 2 assuming a 75.0% yale. E he your merit ype manor soon ues, 252, 0-10Smoles a 02076 x54= 2M a5 = 413, “Too = t odd.- the mattschme S145, 4.0%, Using am inital ade | of 0-205... howe | do oat get this oe macnn3 en - a - 0] 1].[4] When Reection 2 is caried out under different conditions, a compound with meade erm pees Dosti dn map Say tional gu cmp ch eaten, ‘Skeletal formula mars] phe diheeak ction Soe thang ewe Anew wb be wie te , Or fone. avin ete ? Fehon Functionalaroup icuting classicaton __3° ine, [BTA).[5] entity he reagent ad condtons used in Reaction 3 f Haloalewe > alkene — Meare) NAOH in ettarolic ceadlitions, .[[E] Name and outine a mechanism for Reaction 3. (4 mars} Name of mechanism — Ehmination Mechanism ne it HsC-Coc— Ge x fAgC-Cac 4 b % 4 He A on “OH _ a3 | Turn over“The rate equation for the resction between compounds and B is t= KAYE) Figure 2 shous how, n an experiment, the concentration of A changes wth time, fn this reaction Figure 2 Al mot dos Seas ce eaestu te es pes cto aioe a | st lite ceeteesceeem a | []TZ).[2] Use tis targent to deduce the inal ae ofthe reaction, nee 49 oe 22. 0.004 Ee as eon a. a [DT2].[3] Tre-experment was rpssted a the same temperature ang wth the same ‘it cancarra tb Bt wha aero hal conconaon or A ‘The nena rate was 17 tes greater han nthe orga experiment akin ow concen fA rate = kCANL6} = sate aE + CAV increases by Nut ke ot Smid? @ OS x ee AN initial Cone. was O a 3 AS = 0-65 fiom the CAS 285indbt rf Inia concentation of A mater “Turn over forthe next question ‘Turn over6 rd ‘A cares 0! experiments i cried out with compounds © an. Usin the data ‘obtained, tne rate equation forthe reaction between the two compounds ‘Seduced tobe ‘ate ~ (CH) In.one experiment at 25°C, the ital rate of reaction is 3.4 x 10° mol dn?" hen the ital concentration of Cis 048 mal dm and the inal concerraton D1s023moldm= [Caleta vai forthe rate constant at his temperate and give its. units, [3 marks} Fate> KLeICOS foe, SIRO 2k Kz 0-028 mot tdants! | | Sue 048x003 ® ors Unis[2] An equation that roltes th rato constant, othe activation enerny, 7 aan the temperature, Tis nA RT Use this equation and your answer from Question 8. to calculate a value, in kkimor’, forthe activation energy of ts reacton at 25°C. Fortis reaction n= 16.8 The gas constant R=8.31 J! mor (you ware unable to complete Question 34 you should use the value of 32» 10"for the rate constant, This snot the corect vale.) temars} (n 0-028 = é gee cannet - ne be thar Bim ba RT K(UAbaK) naerentber Hem ris am 3) $31 x14 « (16-4 --358) = Ea. €az 50FIG Tool! e100 + oe Ea 90% Kymol —- sett eony — sant ‘Tum overKe ‘Tho aldelyde CH,CH,CH,CH,CHO reacts vith KCN fllowed by cute aco form aracomic modure ofthe two streolsomers of CHyCH.CH.CH,CHOHICN Give the IUPAC name of CH.CH.CH.CH,CH(OH)CN th mart 2-hyjvonyhexane nitrile. Describe how you would distinguish between separate samples ofthe wo ‘stereoisomers of CH,CH,CH,CH:CH(OHJON, (2 marke} sing lowe odarised. [ight each enautioner wold roteabe in opposite directions clan wry the reaction produces a racemie mixture, [8 marks} Bs he Caled cobs afl adel — et 50 the CN con attack th aboweand ow the plane with equa pobability9 ‘siete [814).(2] An isomerat CHyCHichCH:CHO rect wth KCN flowed by cite aid to “| fima'crpoons ina ase tt som sereomenam Draw the siructure ofthe compound formed and justly why it does nt show sloroisorarism (2 marks} swucture | on Clg cl, -C ~ cH cH 1 cw ° calgeni, Cotes bstcation — he pridoch does not combain o chiral | carbon, ‘Turn over forthe next question “Turn over oF10 ‘ie [ors] Ethanoic acl and ethane-12-dio react fogether to form the dlester(CyH<0,) ‘shown, 2CHLOOH() + HOCHICHONI) = CHKOX) + 240M) [5] Draw stucturl formula forthe diester CHO {ma cugc7? FA ecg \o- ¢-¢-07 hou ‘thancle sid an 0.208 mol of ethane 2d. | on ‘A smal anourt of caus was added to a mitre of 0.470 ma of | “The midure was left to reach equilrium at a constant temperature. Complete Table 1 Tet Amount inthe mitre mel cricoon] HocH.cHOH | catiuo, | HO ves | oo | 020s ° ° | ‘At equiibaum 0.180 0-06 O14S: 0-24 | | Phare ae {8 marks} ‘Space forworking 9:28 owas arsbis B36 + ows-0-1ms 20-06 at ibis Hh," one [5] Write an expression forthe equltrium constant, K, forthe reaction. ‘The total volume ofthe mixture doesnot need to be measured to allow & carect value for Kobe calculate. sty the statement Expression feo 2 Leetoogh Cio" Berra wonton [2 marks} suscatien Sane mmber of moles on beth sides of | the equation. [2] Aaatfeent mire of ethanoie se, thane-12-ol and water was prepared {nd et toreach equlbrum at diferent temperature from the experiment in Question 32 | “The amounts present inthe new equlrum mixture ae shown in Table 2. | Toble 2 “Amount i the misture mol CH.COOH |HOCH.CHON | CHO. | HO ‘Atnew Tobe equittrim | cakeutsted | 0764 een | “The value of K, was 6.45 at his dferent temperature, | Use tia value andthe data in Table 2o calculate the amount, mo, of ‘ethanaiczcld present in the new equllrium mitre ‘Give your answer to tho appropiate numberof significant fqures. j " {3 marks] | 645 = 0-402 «(45) ast a it ts He (xJt x 0-264 least yet 304 ime thee, FORME 2 = OFA 645 «0-260 = [Amaun:ofethanoe aid2 aa -—— |ors Use the Data Boodet to help you answer this question, ‘This queston fs about amino acids and peptide amide) inks, [1] Praw te sructure of the zitoin formed by phenyaanine, . te tt maria ote [2] Draw the sruture of serine at high BH it priate, Sal | nF go kigh pl acid wih prte. | By -e-e Zo. we on | | | [3] raw ne ects of bom penis formed when penyatrine eet wth | | In each structure show athe atoms and bonds in the amide ik: 2 marks} | dane aueily Hoy totaly diffrent pooaeks‘An amie nk is also formed when an acyl chloride reacts wth a primary "Name and eutine a mechanism fr the reaction between CH:CHCOCI and CHACHA, Give the IUPAC name ofthe oxganle product Name ctmechanism (Nef) cdditon~ el Mechanisn [6 marks} iminatign ey cayem gfe engemn LE one ye cen = cuyeuly aug © sen sberttch ode Cyc, = CB Cte =? “ty Bomad- fui reas N ethyl propanaonid here be » a chsin once TUPAC name of oganicpradct ‘Turn over° “Tosttubereactons can be used to dently the functional groups in oraric ‘molecules [0171-4] Youare povided wih samples ofeach ofthe four compounds. 4 om oo ox We—E—cooH Hye—-E—oHkon Hye—4—-coon—Hye~$-cH0 bu ra i a K L " " Describe how you could distinguish between al four compounds using the rmiimum numberof tats on eech compound. ‘You shout describe what would be observed in each tet [6 marks} dest 1: Add acidified, potassium dicwomate, toa — Sample of ead KyLand N woud thew @ clear ees chaige of ome > green as thy he beer | Nn exidindl, woud nek. TAD: Add sodinm caencte toa Semlle of ete . Kane Foc 1M would efhowese | ple oftws uid nok . CooH? Aest3: Add silver nibete solution bo asenfl oats - al ole cy aivcech_with recline hydtowide, wrarmeol. anc __acidilek euith nitac acid.) Land N told | give cram fe Kad m wold no » Mest: AY Febtegs slution 4 6 Semple ot cach sacha “ oa © cede nll be prado! hy N bot ook k,Loct Su hanes = — tat i36 = This queston is about itrabenzones. Nitvobeneene reacts when heated with a mitre of concentrated nic acid and ‘oneenraad altri ald to form a mistre of three Bomericdnitobenzenes, ‘Write an equation forthe reaction of concentrated nive acid with concentrated sulfuric a fo frm the species that reacts wth nitrobenzene, Et mar LINOs +JW2S04 —> NGF + HO + ZI ‘Name and outine a mechanism forthe reaction of this species with itrbenzene to fom 1, sedntrabenzeno Name ofmechanism _Clectiophilic. Subs tiuti Mechanisr WA wo, |‘6 ae [3] Thedioerzones shun eres by hin ayer vensegahy Ti | oF oO” | om | tn an experiment, cared out ina fme cupboard, a concenrale soon of pure {,4-cintrobenzene was spotted on a TLC plate coated wih 2 sod that Canta olor bonds. Hexane was used as the solvent ina beaker wih abd, ‘The star Ine, drawn in pond tho final poston ofthe spot andthe final solvent front are shown on the chromatogram in Figure 3 | res Solvent front | Use the eromatogram i ‘bdinivebenene in th Figure 3to deduce the Ry valve of periment. Tick (7) one box. | 1 mark | A oat a | B 046 oO © 0s o D062 re7 od TE].[E] state in general ters what delerines he cstance raved by 2 span TLC. mar . r Relative nghile phase. —taghile pho, Skctioray oud bidet Ja Ani ty [B1[E].[5] Toobin ne drmataga he Tate was a yh gs an ped (Te). ‘in the solvent in the beaker in the fume cupboard. The lid was then replaced a {Gio one ctor practical requirement when placing the plate inthe beaker. tt mark} [ELE]. CE] A seond 16 expen wae care at ng 1 2dnbenne ad CoTs)-41 1.4-dinitrobenzene, An identical plate to that in Question 8.3 was used under Hee olive wis to st mired n cornet Fe relore 1% Sime ws aude pest han bat dhe educa the relative polar of tho 1,2-dntrobonzone and 14-dnitebonzone and explain why 1.4- 6a + Sle with be linomete.~ - 5 E of | pals oF PV x «10°6) us F465 xl0° ms Bom hated " eqgnton, | 2 Codiady rate = & | . 1450, x 10 ary | 272«105% 114 = ¢ si OM ehe 4S no | ter tnai oa [ATOT.T31 lamer cau) 9c compound, The iar spec of P31 eam Siig ie Mapu ob Pg 8 7 Figure 4 a eho Gy eos a Faw Use se spectre an ates Aan nthe Data oot desc the Sree {tyr nme atone piace of vdnce you have ed om ach seen [3 marks] sic _ a Ahis bes 4 Evin tom Figure 4 Co O-Hacid gap @) 2500-3000 4 Gonkeis C7 grog @ (Yo000* - - Eviterce rom Figure 4 Coch worment s a ‘Turn over >2 ass Isomers Rand $ave shown, ° ° r t x SH s St 0 Oty wc Sone nyc So” Sony i ° ° R s Although the °C spectra of R and $ both show the same number of peaks, the spectra can be used to distinguish between the isomer. Justly this statement using Table € from the Data Booklet. {Give the nurber of peaks fr each tsomer. [3 marks] station Suptd have 2 carbons aranh 10-S0ym dete c= but R hes. R peaks wold be “rave domnbieidh due. to his.(ETO).[5] though ne spectra of Rand 8 both how he same number of peaks, the a ag spectra can be used 10 dlsunguis between the Somers. stty this statement using the spiting patterns ofthe peaks, Give the umber of peaks for each isomer. [3 marks} sstifeatior L peaks voold loth be siagkts where as 5 wath be a triple and a quite e@ere ‘ems @ HL Numberofpeaks Both have two peaks . — V eqyintny, ‘Guestion 10 continues on the next page - oO “Turn over >4 Ed (The actor of heat on S-hydromexancic acid can lado two dierent roosts On gentle heating, Shyoxyhexancic acd loses water to forma oye campoune T (CaO) | | Under dierent condtons, 5 hydroxyhexancc aid fms a polyester. Draw the eeuctre fT Draw the repeating unit of the polyester and name th iype of polymerisation | lee re ‘emarks) ShyWirmpperie acik = we Cnbad-g bac cee beads we, A. Lo | ft “ oe oe WH re Fp OS “Type of pomerisation _ Condensai ot.— ([ATO1.[7] tsomer Us shown, vee coodHCH, Cy | u | “The polymer formed by U and the polymer formed by S-hydroxyhexanoic acid Jn Quosion 10.6 both contain ester groups that can be hydrolysed, Draw the repeating unit of tha polymer formed by U. lusty thestatoment that, although both polymer structures contain ester ‘groups, the polymer formed by U isnot badegradable, [3 marks] Repeating unit of poymer formed by U. ¢ CoOetigcHs ee | fo ition ty | -¢-¢-- 4 OO en | tot hh wae ee HCH / wo c usteaton chéin hich is attecle | Contains, Stong C=C bouls (iskas fe Nvalplilie or acid ‘Turn over forthe next question - ‘Tum over ® 2sam. seh Ey “This queston is about the tree amines, E, Fand G. Oo oOo” ‘Amines E,F and G are weak bases, Explain the ference in base strength ofthe three arines and give the oder ‘ofinereasing base stongth ‘emarts] Ahe. stteegth of sey 5 depedent onthe 7 si of th lore prir on the nitrogen. 6 is skh bor pir delocsi . He fing So Lesh aucikMe. & is neat stangest OS the CHacw: t So tlectan deasis IN s0 more qvakbl thn 6, ever tush dee ‘ie GAN ore delecalisstien into Liege F is the stong SH N ic now Aether Lins, antl cl " density also dveched tN sonulet meking (oe Dear ca ‘Amine F canbe prepared in a three-step aymhesia starting from ‘llyibero. | ‘Suggest the structures of the two intermediate compounds. For each top. gv reagents and conditions only. Equations and mechanisms ss are notreqaes, \ [5 marks} Ire (5 marks a ree Rs ats ead “fe he beige city ther Hon‘Ther are no questions printed on this page Do NoT waITe/6N THIS PAGE ANSWER IN THE SPACES PROVIDED ea 00171 tn A