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CIE Mar 2017 v2 Paper 2 Q3
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![11 (a) A series of reactions starting from 1-bromobutane is shown. 1-bromobutane HCN and KCN reaction 1 CH3(CH2)3CO2H PMT OH(aq) reaction 2 but-1-ene polymer (i) Draw the displayed formula of compound P. (ii) Identify the reagent(s) and conditions for reactions 1 and 2. reaction 1reaction 2[2] (iii) Draw the structure of the repeat unit of polymer Q. [1] [2]UCLES 2017 9701/22/F/M/17 [Turn over<br />
12 (b) Complete the reaction scheme to show the mechanism of the reaction of 1-bromobutane with OH(aq) to produce R. Include all necessary charges, dipoles, lone pairs and curly arrows and the structure of R. PMT CH3CH2CH2 Br OH (c) But-1-ene reacts with steam as shown to form a mixture of two structural isomers, S and T. major product reflux Cr2O7 2 / H+ but-1-ene + steam [3] minor product S can be oxidised with acidified potassium dichromate(VI) to form compound U. S and U both react with alkaline aqueous iodine. (i) Identify the type of reaction that occurs when but-1-ene reacts with steam.[1] (ii) State what can be deduced about the structure of S from its reaction with alkaline aqueous iodine.[1]UCLES 2017 9701/22/F/M/17<br />
PMT 13 (iii) Explain why S is the major product of the reaction of but-1-ene with steam.[2] (iv) Draw the skeletal formulae of S, T and U. [3] (v) Write an equation to represent the oxidation of S to U by acidified potassium dichromate(VI). You should use [O] to represent the oxidising agent.[1]UCLES 2017 9701/22/F/M/17 [Turn over<br />
PMT 14 (d) CH3(CH2)3CO2H is a colourless liquid with an unpleasant odour. It reacts with methanol in the presence of an acid catalyst to produce an organic product V, which has a pleasant fruity smell. (i) Name V.[1] (ii) A student analysed CH3(CH2)3CO2H, methanol and V using infra-red spectroscopy. The spectra were returned to the student without labels. Identify which of the infra-red spectra, X, Y or Z, corresponds to V. compound spectrum CH3(CH2)3CO2H methanol Explain your answer with reference to relevant features of the three spectra in the region above 1500 cm1.[4]UCLES 2017 9701/22/F/M/17<br />
15 infra-red spectrum X PMT 1000 500 2000 wavenumber / cm1 1500 infra-red spectrum Y 1000 500 2000 wavenumber / cm1 1500 infra-red spectrum Z 100 transmittance 50 0 4000 3000 100 transmittance 50 0 4000 3000 100 transmittance 50 0 4000 3000 2000 wavenumber / cm1 1500 1000 500UCLES 2017 9701/22/F/M/17 [Total: 21] [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/March_2017_v2_QP_-_Paper_2_CIE_Chemistry_A-level_3-0.jpg)
![9701/22 Question Cambridge International AS/A LevelMark Scheme PUBLISHED Answer March 2017 Marks 2(c)(i) rH = rH{products}rH{reactants} = 2(242)4(92) = 116 (sign AND answer) 2(c)(ii) heterogeneous (catalyst) provides an alternative reaction pathway of lower activation energy 2(c)(iii) reaction is exothermic (increased temperature) shifts equilibrium to the left AND decreases yield of products (Cl2 and / or H2O) / less product formed 2(c)(iv) initial number of moles M1 eqm number of moles M2 mole fraction M3 partial pressure HCl 1.60 O2 0.500 Cl2 1.6020.600 = 0.400 0.5000.600 = 0.200 0.600 0.600 1.80 0.600 =tot p 1.80 5.00104 H2O 0.600 Marks 2(c)(v) Kp = )) 44 4.8 10 3.6 10 (( 3.6 103.0 10 units = Pa1 2(c)(vi) Kp would not change Question 3(a)(i) = 1.05105 Answer 3(a)(ii) reaction 1 = HCl (aq) reaction 2 = (conc.) NaOH / KOH AND ethanolUCLES 2017 Page 4 of 5<br />
Cambridge International AS/A LevelMark Scheme PUBLISHED Answer March 2017 Marks 9701/22 Question 3(a)(iii) 3(b) CC backbone with dangling bonds rest of structure 1 1 1 1 1 lone pair on O AND curly arrow from O to C of CBr dipole on CBr AND curly arrow from CBr to Br product (butan-1-ol) 3(c)(i) (electrophilic) addition S has CH3CHOH OR methyl / CH3 group next to CHOH positive inductive effect of more alkyl groups / more alkyl groups donate electron density secondary carbocation / secondary intermediate is more stable (than primary) 3(c)(ii) 3(c)(iii) 3(c)(iv) S = T = U = 3(c)(v) CH3CHOHCH2CH3 + [O]CH3COCH2CH3 + H2O 3(d)(i) methyl pentanoate 3(d)(ii) (compound V is) spectrum X spectra X and Z show a C=O (stretch) at 1730 (cm1) spectra Y and Z show OH (stretches) above 2500 (cm1) V has a C=O (bond) and no OH (bond)UCLES 2017 Page 5 of 5<br />](https://learnah.org/wp-content/uploads/2018/08/March_2017_v2_MS_-_Paper_2_CIE_Chemistry_A-level_3-0.jpg)
