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A total of 9048 students sa the June 2011 Chemistry examination. Overall, stud at dents performe well. A sco of just ed ore cent while a score of just over 7 per cent wa needed to re 79 as eceive an A. T mean The over 85 per c was needed for an A+, w score for the examination w 60 per ce which corr was ent, responded to t middle of the C+ grade range. These statistics the f at ation proved t be slightly m to more challeng ging than the c corresponding 2010 examin g nation. suggested tha the examina However, the vast majority of students w able to f e y were finish the exam mination, to th best of their ability, within the allotted he r d 90 minutes. significant inst tances in whic students did not make ef ch ffective use of supplied data or informatio for f a on; There were s example, in S Section A, Qu uestion 13. On of the aims of the study is that students are able to a ne s apply their und derstanding of chemistry to both familiar and new si ituations. hat f wered correct and five qu tly, uestions that In Section A, there were 11 questions th more than 60 per cent of students answ per udents answer correctly. red less than 50 p cent of stu Question 8 p proved to be th most difficu question in this section. The majority of students pr he ult n roceeded alon the ng carboxyl + am mino pepti path witho considering the requirem that the product, ibupr ide out ment p rofen lysine, n needed to be more soluble in water than ibuprofen. T question r e n The required students to recogni that a depr ise rotonated carb boxyl group increases solubility, a poin associated w ‘soluble’ aspirin. nt with For Question 9 it was deci n ided that two r responses cou be correct since it was not made clear in the questio that the uld r on ethanol woul most likely be in excess. Even with thi allowance, it was evident that the prop ld is t perties of the r reactants, products and the catalyst in biodiesel pr d n roduction were not well und e derstood. While studen would have performed ti nts itrations as pa of their pra art actical work th hroughout the unit, understa anding of the ‘equivalence point’ was no strong. This was particularly evident in Question 11 e ot s n 1. Question 13 emphasised th importance of not only r he e reading the qu uestion careful but also us lly, sing the suppl data lied The ted nt have encourag many stud ged dents to assum that all the w me water was effectively. T term ‘heat to constan mass’ may h driven off the sample. How e wever, a quick check of n(H2O) removed showed that this was not th case. k H d he The overall p performance on Question 15 was surprisi Many students simply did not make the required u of the o 5 ing. d use ratio n(NaN3)/n(N2). Question 18 challenged stu udents to cons sider the key factors that de f etermine the IR absorption b R band for a cov valent bond. These factors include bond strength and the relative masses of the t atoms in the bond. Ove s d d m two erall question performance showed that m students were drawn t electronega most s to ativity as the k factor. Un key nderstanding o the principle of of es spectroscopy is part of the study. y e Question 20 showed that s students’ unde erstanding of t effect of li the ight from the l light source on the metal at n toms in the flame of an a atomic absorpt tion spectrom meter could be improved. It s suggested that many studen did not ma the t nts ake distinction be etween oxidat tion and the tr ransition of ele ectrons to high energy lev due to the absorption o energy. her vels e of As a part of t their examinat tion preparatio students sh on, hould be enco ouraged to crit tically review multiple-choi questions ice on which the struggle. Te ey eachers are en ncouraged to provide critica analysis and feedback to t p al d their students on their performance on multiple-c choice questio ons. Section B pro ovided studen with a mixt nts ture of questio types and a wide variety of challenges on y s. Performance on Question 1d. reiterated the impressio that biodies is a topic w e on sel worth addressi Question 1f., also ing. ty he r nd) ine linked to fatt acids, required students to recognise th need to use the ratio n(Br2)/n(compoun to determi the number of C= bonds present in each m =C molecule and t then identify w which of the th fatty acid in the list q hree ds qualified. Responses to Question 2 demonstrated t challenges that descript responses pose for som students. It appears that o d the s tive me the message about the need for a (+) cha arge on specie causing pea on a mass spectrum is n yet well kn es aks not nown.
Chemistry GA 1 Exam © VICTORIAN CURRICULUM A AND ASSESSME ENT AUTHORIT 2011 TY 1
Chemis stry GA 1: Written examina 1 n ation 1
i this case th mass spectru in terms o the context in he rum. the n Question 4a. the fundamental principles of fractional dist f cussion of the method of co ollection of an ester and sep n paration of an ester from wa and ater collection of an ester. the number 1 and 3 are an essential part of the systematic name and are used rs p because alter rnative locatio of the meth and/or hyd ons hyl droxyl groups would repres a differen compound. the calculated pe ercentage P2O5 should have been the sam for both tec e me chniques. related to the use of correct systematic nomenclature. In the chemic name t cal Questions 7a and 7aiv. and 5bii. Co onfusion resul for those students who felt the need t use all the lted to relevant to ge data. In Questi ions 5bi. proved challe enging for a m majority of stu udents. C on oth s. emphasised that interpret d tation of the su upplied data. aiii. while H2SO4 or H2SO4(l) were acce O eptable as repr resenting ‘con ncentrated’ sul lfuric acid.. in Quest tion 3c. suggested that. but few were a to effectiv argue for separation fro the acid. Question 5a. With ca alculations rel lated to back-t titration. Stu udents seemed more d -based calcula ations. on seeing t words ‘fra o . of t on nge ificant proport tion of studen Many misr nts. while others focused on the relativ abundances of the atoms rather than th molecular io Question 2b. most st tudents interpreted th question as if the moistu in the origi precipitate (in 4a. requ uired students to draw a stru ucture of an alcohol produce from a chlo ed oroalkane. the actional distillation’ in the q question. in thi case in part is ticular. This is a skill tha is regularly a at assessed and xpected to be p proficient. The req quirement to ‘ ‘explain how t evidence p the provided by ndicated that a complete sep paration of ba anana oil from the reaction mixture had been achieved’ was not well m m ’ l the spectra in interpreted. Disc unreacted aci and alcohol is a logical a id l adjunct to coverage of ester production. ‘excess/unre eacted’ and ‘re eacted/reactin appropriate ng’ ely. eed re s at should be dil luted. In Question 7 7av. Err included rors issues. Responses to Question 7b. ts tify etting to the so olution most e efficiently. and 4b. T question t This tested student ability to ts’ apply their un nderstandings in different s s situations. were valid deliberate an accurate. nd Consequently. e ot l not he up Chemistry GA 1 Exam Published: 3 November 2011 2 . ntinued to resp pond well to questions on N NMR spectrosc copy. Many students inc ic y correctly inclu uded the numb ber. of the questio was that bo techniques in 4a. For exam e mple. when suggesting tha a solution e n e. en n Question 5b. The key factor de e etermining dif fferent boiling temperature in a mixture g of substances is intermolec s cular attractio on. many students y immediately defaulted to t fractional d the distillation of crude oil and fractionating towers rather than addressing the f d g r tillation as it a applies to a range of separat tions or. ‘to bri the peak a within ing area the range of t calibration graph’. was a stoichiometry questi that includ much data The challenge for student was to ident the data ion ded a. it is app propriate that p parameters be set. A useful t able vely om ensuing discu ussion point m might have bee how the information on the ester spectrum alone sh en hows separatio from the on acid and the alcohol. assessed stud dents’ ability t write and co to ombine half-e equations. In Question 4b. provided stud tion 7aii. dents with an organic reacti pathway. n handled. was well ve s he ons.. r 3-methylbuta an-1-ol (3-met thyl-1-butanol). T associated questions re ion The d evealed some s significant Question 7a. Ma students w provided a correctly ba any who alanced oxidat tion halfwith which students are ex equation in Q Question 5ai.201 11 Assess sment Rep port Question 2aii. espresso coffee chromatogra and am ignored the p presence of the peak area in the data table Students ne to be awar that. read or misunderstood the l label on the yof the questio is a challen for a signi axis. Quest the incorrect number of ca arbon atoms an inappropria representa nd ate ation of the bo between th hydroxyl gr ond he roup and carbon. Students con In answering Question 3ci most students focused on the truncated peak on the e g i. On an s sent nt ethanol mole ecule there is n other possi location b C-1 for the hydroxyl fun no ible but e nctional group so there is no number in p o the systemati name. it was ne 5 ecessary to – m work out the number of mole of Cr2O72– three times. H2SO4(aq) was not. Most students we able to link the informat ere k tion provided on the 1H NM spectrum t molecular s MR to structure. In Question 8 the main errors were no ‘showing all bonds’ and n showing th amino grou as protonated. d. 8c.) had been an exper he s ure inal e rimental error The intent r. Question 7c. In prepa aring for exam minations stud dents should b encouraged to think throu the calcul be ugh lation steps be efore beginning a s solution. rathe than just usi the data in the order in which it appe er ing n ears. S Some students were able to draws links between the al s b lcohol IR spec ctrum and the banana oil IR spectrum to R argue for sep paration from the alcohol. did not accura d ately combine it with a give reduction half-equation in 5aii. stude should us labels such ents se comfortable with titrationas ‘supplied’. was a stoichi iometry questi that was h ion handled much better than Qu uestion 4a.
So when ibup . The negati ion. The correct answer is in nts e t ndicated by shading. an Option C w would result from a conden f nsation reaction be etween the –C COOH group o ibuprofen on and the – 2 group on lysine.2. The biodie ethyl stea esel arate is produc via the ced reaction: c canola oil + 3 ethanol 3 ethyl stearate + glycerol in the pres sence of potassium hydroxid catalyst. H su ubstituted by Br. de 5 76 12 9 4 0 6 15 19 8 58 1 7 6 7 79 8 0 8 7 10 77 6 0 9 38 31 17 14 4 0 Chemistry GA 1 Exam Published: 3 November 2011 3 . CH CH and ethano acid (CH3C oic COOH) all dis ssolve in 75 5 13 7 0 1 water via h hydrogen bon nding. –N 2. X is the bo between a ond amino acid res sidues in the primary st tructure of the protein. r n Option D would result f w from an acid-b base reaction between th –COOH gr he roup on ibupro ofen and the –NH2 gro on lysine. 2 3 4 3 2 12 80 2 8 12 95 73 5 1 7 0 0 0 The molec cular formula of 2. optio D best sho on owed the structure o ibuprofen ly of ysine. l ave structure th enables it to dissolve in water more hat n readily tha ibuprofen. must ha a ct. dissolves via ion-dipole and hydrogen b bonding.201 11 Assess sment Rep port SPECIFIC INFORM C MATON Section A – Multiple-choice question ns The table be elow indicates the percent tage of studen who chose each option. Y is the bo formed when –SH on th side ond w he groups of cysteine mole ecules reacts in n establishin the tertiary structure of th protein. group. ng he The covale S–S bond formed is also known as a ent o disulfide b bond. hen molecules gain H+. This product would oup t dissolve in water via ion n n-dipole bond ding and hydrogen b bonding. X – 1. This covalent e s bond betw ween C and N in the linking peptide group is al known as an amide bon lso nd. forme when ibupr ive ed rofen molecules donate H+. The product –NH n would diss solve in water via hydrogen bonding. di issolves via io on-dipole bonding. All amino acids contain the amino.4-trime ethylpentane is C8H18. ethylamine (C 2CH2NH2).1. Ibuprofen lysine is more soluble in w e water than ibuprofen. n NH which is b basic and woul be expected to react ld d with 1. The positive io formed wh lysine T on. Ethane (CH3CH3) is non-polar and is less soluble in water r.2-trichloroethen ne Step 2 is a substitution r reaction. Since ion-dipole bondin is stronger than ng hydrogen b bonding. profen reacts with lysine the produc ibuprofen lysine. o % No Question %B %C %D Com mments %A Answe er Ethanol (C 3CH2OH).0 M HCl(aq).
ce om Since ther was 25. were 0. hen 2 mol H nce CH3CH2O 2 mol C 3COOH OH CH Step 3: 2 m CH3COOH mol 1 mol Ca(CH3COO)2 + 1 mol CO2 C Step 4: 1 m Ca(CH3COO)2 mol 2 mol CH4 + 1 mol CO2 Total n(CO2) produced = 4 mol O n(CH4) pro oduced = 2 mol m Ratio n(CH4) produced : n(CO2) prod H duced = 2:4 = 1:2 Since the C 4 and the CO2 may be as CH C ssumed to be collected a the same tem at mperature and pressure. the correct answer was H. or the amoun of NaOH(aq required to reach the nt q) equivalenc is the n(H+) available fro the acid.20 M NaOH(aq) is required to unt s reach the equivalence point for both a e acids.0×10–3 = 2. om Step 1: pr roducts are 2 mol CH3CH2OH + 2 mol C 2 O CO Step 2: all the CH3CH2OH from step 1 is p co onverted to CH3COOH.8 4 10 8 56 27 10 0 0 11 17 45 32 6 0 12 12 15 61 12 2 0 Chemistry GA 1 Exam Published: 3 November 2011 . the key facto influencing w . the et thanol should be in excess to ensure complete reac c ction of the can oil. n layer B mu contain gly ust ycerol. so s Consider t amounts of CH4 and CO2 produced the o O starting fro 1 mol C6H12O6. H for titratio is the same for each acid. the n(NaOH) r required is the same for bot acids. lue a . d the ratio V(CH4) produc V(CO2) pr V ced: roduced equals 1:2. potass sium hydroxide and unreacted ethanol. th equation fo the titration reaction in he or both cases is s HA(aq) + NaOH(aq) NaA(aq) + H2O(l) Since the n n(HA) is the s same for both acids. this was not m made clear in the question. Hence. Accord ding to the informatio in the table: on Thymol bl is yellow above pH = 2. Representi the acids b the general formula ing by l HA(aq). e th This quest tion required s students to ma effective ake use of the information in Table 11 of the Data n f Book (Aci id-base Indica ators). Ideally. nola However.10 Mn(acid) pre esent = 0. When a str rong base suc as NaOH(aq is added to ch q) an acid. and it was possible that students may have y assumed th the ethano and canola o were hat ol oil present in the exact stoichiometric rat for tio complete r reaction. and ionic KOH On this basis. the on . Hence.0 mL of both acid and both re L ds. Thi separation is reflects the non-polar na e ature of the bi iodiesel as distinct fro the polar ethanol and gl om e lycerol. t option D.0×10–3 mol Both acids are monopro so the n(H+) available s otic. option A was als accepted as correct. layer B would his contain on glycerol an potassium h nly nd hydroxide.201 11 Assess sment Rep port Question %A %B %C %D o % No Answe er Com mments Since the e ethyl stearate is collected in layer A.10× ×25. weak or strong. In th case. same amou of 0.
3 Phenolpht thalein is colou urless below p = 8.e. ut n(CaSO4.0 L w due to ion bag was the release of N2(g).0 = 1. H s) d(gas) = 2. the V(N2) pre e .86 grams per litre at STP r Volume of 1 mol gas at = 22.31 × (36. 499 H2O molecu will be m 9 ules produced during the con d ndensation po olymerisation reaction. i.0 = 90000 – 8 8982 = 81018 g m –1 mol Option C ( 000 g mol–1) overlooke the (90 l ed 5 13 33 38 14 14 4 1 14 6 14 18 61 1 15 28 59 10 3 1 16 2 69 25 3 0 Chemistry GA 1 Exam Published: 3 November 2011 . Teach should en a hers nsure that students use the Data Book throughou the study.3. emical formula of the product of the reaction must be f o n CaSO4.0 = 97. a Overall pe erformance on this question suggested n n that a sign nificant numbe of students were unable er to effectiv interpret t informatio in Table 11 vely the on of the Data Book.9 g If the starc molecule is formed from 500 ch s m C6H12O6 molecules. leaving 2 – 1.4 86 = 64.4 L f t Hence the M(gas) = 2. This is co H onsistent with the equation h 2CaSO4.2 2O) = 172 2H 2.½H2O.0 8.2 2O) reacting n(H2O) rele 2H g: eased = 1:1.1 g mol–1 M(SO2) = 64. esent at 100 kPa and 36 6.41 mol According to the equation for the reaction g n(NaN3)/n 2) = 10/16 = 5/8 n(N Hence n(N 3) = (5/8) × n(N2) NaN ) = (5/8) × 2. must Alternativ vely.½H2O(s + 3H2O(l).201 11 Assess sment Rep port Question %A %B %C %D o % No Answe er Com mments Methyl red is yellow ab d bove pH = 6.51 mol 1 m(NaN3) = n(NaN3) × M(NaN3) = 1.0 mol 000 The loss in mass during heating was d to the n g due release of H2O. i.6C = 62. n(H2O) rel leased = 27.5 = 2:3 So the coe efficients of CaSO4.6+273)] = 2. M(starch) = 500 × M(C6H12O6) – 49 × M(H2O) C 99 = 500 × 180 – 499 × 18 0.3 and belo pH = 8.50 mol The ratio n(CaSO4.2H2O an H2O in the nd e equation m be in the ratio 2:3.5 mol H2O.1/172.1 = 1.e.51 × 65.0/ /18.0 L n(N2) prod duced = P(N2) × V(N2)/RT = 100 × 62.3 and pH = 8.5 in the hydr rated compou so the che und.1 g mol–1 The inflati of the airb to 62. = ½ mol H2O remaining .2H2O(s) 2CaSO4. 1 mol Ca 4.41 = 1. between ow pH = 6.0/[8.3.8 × 22.3 pH This sugge that the pH of the solut ests H tion was above pH = 6.2H2O rel aSO leases 1.
–1 C–H bond (bond energ 410 kJ mol– ) are ds gy stronger th C–O bond (bond energ 326 kJ han ds gy mol–1). Because th absorption of energy by the Cu atoms he in the flam from the lig source doe not cause me ght es 17 71 11 6 12 2 0 18 51 20 17 11 1 19 26 6 5 62 2 0 20 12 40 29 18 0 Chemistry GA 1 Exam Published: 3 November 2011 6 . The mass effect can be attributed to t ‘different’ the atom in th C–O and C– bonds. but are not lost rgy t from the atoms. the smaller the e distance tr ravelled up the stationary ph e hase and the lower the Rf value. The lighter H he –H e atom prod duces a higher vibration freq quency. y proportion to the frequ nal uency of the I radiation. but may be co ompared to stif springs that can be ff t stretched and bent. a The exact frequency (w wavenumber) a which a at given vibr ration occurs i determined by the is strength of the bonds in f nvolved and th masses of he the atoms in the bond. ene rgy ergy emitted i in the green is n region of the visible spe t ectrum. So. In thin-lay chromatog yer graphy. and the vib brational ener rgies of molec cules have defined en nergy (quantum levels (stat in the m) tes) same mann as electron energy lev ner nic vels. the low IR wavenu wer umber for bond stretching in d a C–O bon can be attrib nd buted to larger atomic mass r of oxygen atoms compar to hydroge atoms. As the light from h e the Cu lam passes thro mp ough the flame electrons in e. When CuS 4(aq) is intr SO roduced into a atomic an absorption spectrometer the sample i atomised n r. IR which is p proportional to the wavenum o mber. is in the high temperature flame. Aqueous s solutions containing the Cu2+(aq) ion are blue be ecause in the p presence of w white light they absor wavelength in the red re rb hs egion of the visible spe ectrum. Transition between vib ns brational energ levels gy depend on absorption of infrared radi n f iation of energy ma atching the dif fference betwe een vibrationa energy level The energy absorbed is al ls. red en A mixture of hydrocarbo molecules would be on quite volat and most effectively sep tile e parated into its compon compoun by gas chro nent nds omatography. so the IR radi iation required to bring abo the d out transitions to higher vib s brational energ levels in gy C–H bond will be of hi ds igher wavenum mber than for r C–O bond ds. n the Cu ato in the flam absorb ene oms me ergy and are promoted to higher ener levels. Each comp ponent could then be identi ified by mass spectrosco opy. At ordinar temperature covalent bo ry es onds vibrate. the stro onger the adsorption to the station n nary phase. As exci electrons return to a ited lower ener levels. Covalent bonds in mole b ecules are not rigid.201 11 Assess sment Rep port Question %A %B %C %D o % No Answe er Com mments condensati nature of the formation of starch ion t from gluco ose. and so transmit wav o velengths in the blue re egion.
and 1f. that is. an outli answer (or answers) is provided. . n(Br2) reacting = 0.6 6 0 64 1 36 Ave erage 0. Marks % D and E 1d.. .9 0 0 65 1 35 Ave erage 0. In some cases the answer given is not the on answer ine r p e n nly that could ha been awarded marks. Marks % H 1c.320/160. l 1a. Marks % B 1f. Str hyl ructure F was t only ester the r Most student overlooked the fact that b in the table o structures pr of rovided.0 = 0 0.4 0 ts biodiesel is ge enerally a meth ester of a fatty acid.4 0 Students needed to realise that to react w Br2.201 11 Assess sment Rep port Question %A %B %C %D o % No Answe er Com mments loss of electrons from th atoms. oxid he dation does not occur. Struc cture E was ch hosen by many students. Marks % A 1b. Sin 0. Marks % F 0 15 1 85 erage Ave 0. carbon-ca =C t arbon double bonds. this ques d stion was well done. each mo olecule of the s substance must contain two C=C bonds.002 mol. A similar calc o culation was r required on th 2009 he examination. Section B – Short answer q questions For each que estion.001 mol of the substa nce ance reacts completely with 0. ind y dicating that they did not re t ealise that while glycero is a product of the production of biodiesel by transe ol t esterification it is not a com t mponent of bio odiesel. Marks % F 0 10 1 90 Average 0. 1e. the s with substance had to contain C= bonds. ave Question 1 With the exc ception of Que estions 1d.9 0 0 10 1 28 2 63 Avera age 1. Chemistry GA 1 Exam Published: 3 November 2011 7 .9 0 14 1 86 Ave erage 0.002 mol h Br2.
[C2H579Br]+ and m/z = 110. this was abou the differen peak heights with the high peak ut nt s her given about t molecular ion peaks. ons the peak at m = 108 bein 60 per cent abundant sug m/z ng ggested that th ‘relative abu he undance’ scal in the conte of mass le ext spectroscopy where the mo abundant s y ost species is set at relative abu a undance 100 w not well u was understood. 2bi. Th ms =C herefore. One mark for reference to the molecular ion peaks (ei r r ither of): the p peaks at m/z = 108.e. han at ] Performance on this questi suggested that many stu e ion d udents struggl to effectively interpret a led and/or use the information the undamentally. [C2H579Br]+ is slig ghtly higher th the peak a m/z = 110. A number of students focu f used on the pe eaks for 79Br a 81Br rather than the molecular ion pea Expressio such as and r aks. i. [C2H581Br]+ are approxim m mately the same height e the p peak at m/z = 108. Marks % Structure 1 0 4 1 7 2 89 Avera age 1. Unsaturated fatty acids w the same n OH d with number of C a atoms as a satu urated fatty ac have two cid fewer H atom for each C= present. i.e. i. C13H27COOH – saturated s C17H31COOH – polyunsaturate with 2 C=C bonds p ed C C17H29COOH – polyunsaturate with 3 C=C bonds p ed C Question 2 2ai.e. F and G (see b hree ds below) . Chemistry GA 1 Exam Published: 3 November 2011 8 .201 11 Assess sment Rep port There were th fatty acid in the table. i. [C2H581Br]+. D. Fu height at m/z z=108 indicati a greater a ing abundance of t lighter mo the olecule – the one with the lighter Br atom o m. peaks on a m spectrum carry a positi charge. 2 Avera age 1 0 Marks 33 25 43 4 1. F. Th issue has al arisen on p 2aii. Satura fatty acid have the gen ated ds neral formula CnH2n+1COO or CnH2nO2.1 % One mark wa awarded fo a description of relative a as or n abundances (ei ither of): 79 the r relative abund dances of the 7 Br and 81Br isotopes are a approximately equal y the 79Br isotope is slightly mor abundant th the 81Br iso s re han otope.9 Structu 2 ure This question was well don n ne. Marks 0 1 42 58 5 % [CH3CH2]+/C 3CH2+/C2H5+ CH Avera age 0. options D. Stud dents need to b aware that the species pr be roducing Students did not perform as well as expected on this q mass ive his lso previous exam minations.6 6 a question. G.e.
aide in part by t fact that it was possible to access full marks his was ed the l without refer rring to the splitting pattern on the spectr n rum. the peak area could not be m o as measured. Many stu udents who did refer to the s d signal splitting explained it g t very well. the pe area of eak the largest pe (caffeine) for espresso c eak coffee was giv in the resu summary table. While many responses refe ferred to dilution.9 % 9 There is no p peak at the rete ention time of caffeine/no p f peak at 96 sec conds. and a qua artet for H on C CHBr2 attache to CH3. Question 3a. – a ublet for three hydrogen atom on CH3 att ms tached to CH2Br. solutions ma not be accur Many incorre responses referred to the caffeine pea on the chrom ect e ak matogram rath than the calibration grap and her ph argued that since the top of the peak wa not visible. Ho owever. he ts Possible resp ponses include ed: the N NMR spectru of CH3CHB 2 shows two sets of peaks um Br o s/two signals the N NMR spectru of CH3CHB 2 shows a d um Br doublet and a q quartet this is consistent with the struc cture because t there are the t different h two hydrogen envi ironments – one for the ee toms on CH3 a attached to CH2Br. ue ated . on standard ay rate.3 % 3 The caffeine peak area is beyond the ran of the cali b nge ibration graph Extrapolatio outside the range of the s h. ven ults 3cii. ed dou Overall perfo ormance on th question w strong. uch e Chemistry GA 1 Exam Published: 3 November 2011 9 . St tudents continu to do well on NMR-rela questions.2 % Dilute the esp presso coffee sample (eithe of): er to b bring its caffeine concentration within the range of the calibration cu e urve by a factor > 12.7 128 ppm (126–129 ppm w accepted) was on on accurate readin of the graph. 0 1 2 3 Average e Marks 14 6 23 58 % 2 One mark ea was award for: ach ded circling the correct structure in Question 2bi (Structure 1) n i. t ctor ld the purpose o the dilution with respect to using the c caffeine conc centration with the range of the calibrat hin tion graph. Re esponses to su questions should not be superficial. 0 1 Avera age Marks 71 29 2 0. 0 Marks 1 Average 33 67 % 0. 0 Marks 1 Average 82 18 0. ropriate refere ence to the sig gnals on the 1H NMR spectr rum appr a de escription of th different H environment in the two compounds. ng Most errors o this questio were associated with ina 3b. to of n calibration cur or suggest a dilution fac that woul bring the rve. 3ci. and one for the H on CHBr2 attach to CH3 H e hed thre hydrogen at this is not consist with CH2B tent BrCH2Br structure in which all H atoms are in the sam environmen h me nt the splitting patte is consisten with the dif ern nt fferent hydrog environme on the CH3CHBr2 struc gen ents H cture. 0 age Marks 1 Avera 12 88 8 0.201 11 Assess sment Rep port 2bii. the term o its own was not sufficien Students were expected t either state on s nt.
that o he s o ant 4b.441×10–3 m × 142.6H2O) accu urately calcula ating n(P2O5) accu urately calcula ating the m(P2O5) accu urately calcula ating the perce entage P2O5 to four signific figures. Question 5ai. wit most studen not linking it to th nts g n(MgNH4PO4. o cant Many studen struggled to correctly ide nts o entify the data relevant to th calculation and attempt to use all d a he ns ted data.141 g / 2 245. nt tion was that t precipitate collected had been deliber the e d rately heated above 100 C to a The key poin in this quest completely c convert the pre ecipitate to Mg 4PO4 bef gNH fore weighing.5 % 2– + 3TeO2(s) + 1 2O7 (aq) + 8H (aq) 3 2TeO4(aq) + 2Cr3+(aq) + 1H2O(l) 1Cr 3H Chemistry GA 1 Exam Published: 3 November 2011 10 . So while the mass of pr now t recipitate collected will be lower. p of Correctly cal lculating the n 2O5) was pa n(P articularly cha allenging.441×10–3 m m(P2O5) = 8. he nd 5aii.688×10–2 mol n(P2O5) = ½ × n(MgNH4PO4. Marks 0 24 % n(MgNH4PO4. because the m of precip .6H2O). O l) aq) Most errors w this equa with ation were asso ociated with th location an number of H+(aq) and e–. tion was that i was known t the it that precipitate co ollected was n MgNH4PO4.7 % Either of: TeO2(s) + 2H2O(l H2TeO4( O l) (aq) + 2H+(aq) + 2e– 2– TeO2(s) + 2H2O(l TeO4 (a + 4H+(aq) + 2e–.6H2O NH O). 2O) in 5a.201 11 Assess sment Rep port Question 4a. be ecause: no P is lost on heating the prec cipitate the mass of the pr recipitate is di ivided by the M(MgNH4PO4) in calculati the percen O ing ntage P2O5.3 g mol–1 2 = 1.6H2O) H mol = 8. The key to an efficien response wa realising that all the P in 3.141 g o MgNH4PO4.256 g of fer nt as rtiliser ends up in 4.6H2O. T was This Some studen did not gain full marks b expected bec cause all data t needed to be used in th calculations was given to four significa figures.6H2O) and n(P2O5) = ½ × n(P) H then n(P2O5) = ½ × n(MgN 4PO4. the calculated l n(MgNH4PO4) will be the same as the n O n(MgNH4PO4.6H mass pitate is divide by a lower ed molar mass. This question was intended to test the mo able stude n d ore ents.81 % One mark ea was award for: ach ded corr rectly calculat ting n(MgNH4PO4.199 / 3. Marks 0 1 Average 56 44 0.6H2O) O 1 20 2 21 3 22 4 13 Average 1.8 = 4. The implicat . 0 1 2 Avera age Marks 72 6 22 0. nts n because their f final answer w not given t four signifi was to icant figures.0 g m –1 mol mol = 1. Sinc n(P) = n(M O ce MgNH4PO4.5 % The same. 0 1 Average Marks 34 66 0.199 g 6) % P2O5 = (1.256 × 100 = 36.
equations to give the overa redox equa 5b.72x10-4 = 1.1 % – n(TeO2) = 3 × n(Cr2O72–) reacting –3 = 3 × 1.6482 g . and 5bii.5 526×10 mol l = 1.5 526×0–3 – 1. 5biii.0 × 10–3 mol [1. (u 2– Students needed to multipl the n(Cr2O72–) reacting a calculated in 5bii.8 Many studen were confu nts used about the classification of dichroma ions – ‘sup e ns ate pplied’. 0 1 2 Avera age Marks 35 19 46 4 1.201 11 Assess sment Rep port Many of the students who had provided the correct an d nswer for 5ai.. Further atte all ation.062×10 m mol m(TeO2) = 4.00 0×10–3 –3 = 1.6 g m –1 mol mol units needed to be included) o ) = 0.72×10–4 mo ol plied n(Cr2O72–) supp n(Cr2O72–) react ting = 0. did not comb the two half-equations effectively. dents used an incorrect mol mass. .. bine or ention should be paid to the combination of halfe n An incorrect coefficient fo H2O(l) was quite common.354×10– –3 = 4.0 03052 × 50. ‘in ex xcess’ and ‘rea acting with the tellurite’. that of H2TeO4.062×10–3 m × 159. s led matics of such questions ef h fficiently. While most students handl the mathem .035×10–3] 035 n(Cr2O72–) in excess (unre n eacted) = n(Fe2+)/6 = 1. which was surp lar w prising since M M(TeO2) was equation in 5 Some stud given at the b beginning of t question. logi sequencin proved ical ng challenging f some. for 5bi. = 0. by the mole ratio for TeO2/Cr2O72 from the ly as n r 5aii.0 0525 × 19.035×10–3/6 = 1. Average Marks 1 2 3 4 0 14 8 12 16 50 % 2.71 x 10–3 = 1. the Chemistry GA 1 Exam Published: 3 November 2011 11 .3 354×10–3 mol l n(Fe2+) 5bii.
Howe ever. and that t it d hat there were tw CH3 wo groups bonde to carbon n ed number 3. The general groups ‘sugar’ and ‘nitrogen base’ were given i instead of the specific comp pounds ‘deoxy yribose’ and ‘adenine’. 0 Marks 26 % 12 hydrogen bonds nts r f ply he ree h Many studen were either not aware of or did not app the fact th there are thr hydrogen bonds in each G–C link and two hydr rogen bonds in each A–T li n ink. Chemistry GA 1 Exam Published: 3 November 2011 12 . 2 13 3 76 Average e 2.201 11 Assess sment Rep port Question 6ai.8 T G 6aii. 1 0 Marks 20 80 % Any of: OH– NaO OH pota assium hydrox xide. it wa not necessar to show all han ure ll as ry l Given that th question ask for a struc bonds. Marks 0 6 % G A 1 94 T Average 1 A C C T 1 74 A Average 0. 0 1 Marks 8 4 % All of: phosphate phosphoric acid/p deox xyribose aden nine. Marks % Average 0. 6b. 7aii.6 Students who did not gain full marks on this question often did not correctly nam all the reac o n n t me ctants. it had to be clear that i is the O end of the OH th is bonded to C. an so had to be d was l om nd HOCH2CH2C CH(CH3)2. it w surprising that many st was g tudents showe a structure with the incor ed w rrect number o carbon of atoms. Question 7ai.8 0 37 1 63 Average 0. Since the pat thway showed that that B w an alcohol produced fro ClCH2CH2CH(CH3)2.7 he ked cture rather th the structu showing al bonds.
7av. g the compounds ar collected in order of incr nses d ional distillatio of crude oi with emphasis on the frac on il ctionating Many respon to this question focused on the fracti tower and co ollection of hy ydrocarbon fra actions at diffe erent levels in the tower wit minimal ap th ppropriate.6 Ethan-1-ol or 1-ethanol wa a relatively common resp r as y ponse for this question. Given th the produc hat ction of esters int al overed in this unit. Many students referr to a dimet red thyl option rat ther than identifying the longest chain of C atoms. hence th number is not part of the systematic p he n e name. not mole ecular mass. A relativ common error was to vely n give the answ as H2SO4( wer (aq) or dilute s sulfuric acid. Chemistry GA 1 Exam Published: 3 November 2011 13 . Sulfuric acid is used as a catalyst in ester produc n d c a n ction.9 d . this is n the system not matic name.5 % 3-methylbuta an-1-ol or 3-m methyl-1-butan nol ance data for t part of the question ind this dicated that many students who had the c w correct structur in 7aii. did re The performa not provide a correct name for the comp e pound. 0 Marks 49 % Any of: H2S 4 SO sulf furic acid H2S 4(l). hould be awar that the key re y factor that in nfluences boili temperatur is the streng of intermo ing re gth olecular attrac ction. n 7aiv. how wever. 7b. SO 1 51 Average 0. 0 1 Average Marks 48 52 0. Marks % Reaction II 0 15 1 85 Average 0. 7avi. 0 1 2 Avera age Marks 31 42 26 1 % Compounds in the mixture are separated according to their boiling temperatures/intermolecular attraction a (any of): e d o and the most volatile compound (lo owest boiling temperature) will be collec first (at th lowest temp cted he perature) compound (hi ighest boiling temperature) will be collec last (at th highest temp cted he perature) the least volatile c re n reasing boiling temperature. Marks % Ethanol 0 44 1 56 Average 0. in t context of the f the question.201 11 Assess sment Rep port 7aiii.5 This question was poorly done. reference to t role of boi the iling temperat ture or intermo olecular attrac ction. awarene of the techn ess nique by whic an ester is s ch separated is the endpoi of chemica pathways co from other co ompounds pre esent in the rea action mixture is a reasonab expectatio Students sh e ble on. Ethanoic acid is produced from ethanol by oxidation. There is no o other option fo the –OH fun or nctional group but to be on C-1.
NH2 or NH3+. 0 1 Marks 18 20 % Both of: boxyl or COO OH carb amino. NH3+ was accepted because in 6 M HCl it i fair to assum that the NH2 group on e nal H n is me H the amino ac would be protonated. 0 1 2 Avera age Marks 46 50 4 0. cids Students should be aware that the hydro t olysis of proteins converts p peptide groups in amino and carboxyl gro s d oups. e a While slightl more than half the studen were able t argue effec ly h nts to ctively that the was no alc ere cohol present.201 11 Assess sment Rep port 7c. Since the reaction mix on ad e xture would ha contained ave ethanoic acid and 3-methy d ylbutan-1-ol. H 2 62 Avera age 1. with a s significant number of stu udents sugges sting that it wa an O–H (ac band. few were able to expla how the ba ain anana oil spect trum showed t the acid w not presen Many students gave reas that was nt. but that w not releva to the ques ed a was ant stion. T is not This pres on the spe sent ectrum of ban nana oil the IR spectrum of banana oil d o does not show an O–H (acid) (2500–3300 cm–1) absor w rption band. Stud as cid) dents should h have been able to recognise the e characteristic broad shape of an O–H (a c acid) band. Question 8a. Marks 0 21 % 1 79 Average 0. he 8b. it was necessar to indicate how the spect showed the lack of the a or the t ry tra acid alcohol in the final banana oil product. sons how the banana oil sp pectrum showe that banana oil was an ester. Chemistry GA 1 Exam Published: 3 November 2011 14 .8 The side grou on the bra ups adykinin mole ecule section should have en s nabled students to identify t amino acid from the ds Table 8 of th Data Book. Students wer required to explain how t evidence provided by th spectra supp re the p he ported the cla that ‘comp aim plete separation of banana oil fr f rom the reactio mixture’ ha been achieved.5 It was decide that either t name or th chemical fo ed the he ormula of the functional gro oups was a rea asonable respo onse to ‘identify’ the two function groups.6 % Both of: com mpound B has a distinct O–H (alcohol) ab H bsorption band around 3300 cm–1 (3200– d 0 –3550 cm–1). There was so confusion around the a ome n absorption ban near 3100 c –1 on the ba nd cm anana oil spect trum.
w on uded missing atoms and eit ther not includ ding the positi charge or showing it as an H+.4 A surprising number of stu udents did not show the O– bond. ive s Other commo errors inclu Chemistry GA 1 Exam Published: 3 November 2011 15 .201 11 Assess sment Rep port 8c. Marks % 0 59 1 41 Average 0. despi the instruc t –H ite ction in the question to show all bonds.
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