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CIE Nov 2014 v1 Paper 4 Q4
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![10 PMT (a) Methylbenzene undergoes electrophilic substitution with nitronium ions, NO2 +. Nitronium ions are generated by the reaction between concentrated sulfuric acid and concentrated nitric acid. (i) Construct an equation for the formation of nitronium ions, NO2 +, by this method.(ii) Complete the scheme to show the mechanism for this reaction. Use curly arrows to show the movement of electron pairs. CH3 NO2 [4] (b) (i) Describe and explain the relative acidities of chloroethanoic acid and ethanoic acid.(ii) Describe and explain the relative acidities of phenol and ethanol.[3]UCLES 2014 9701/41/O/N/14<br />
PMT (c) Phenyl 2-hydroxybenzoate is an antiseptic. 11 OH phenyl 2-hydroxybenzoate Complete the following table about the reactions of phenyl 2-hydroxybenzoate with the three reagents. reagent structure of product(s) type of reaction Na excess Br2(aq) excess hot NaOH(aq)UCLES 2014 9701/41/O/N/14 [6] [Total: 13] [Turn over<br />](https://learnah.org/wp-content/uploads/2018/08/November_2014_v1_QP_-_Paper_4_CIE_Chemistry_A-level_4-0.jpg)
![Page 6 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 41 PMT [4] [3] [16] (ii) 2+ 6 [Ca ] = 32.5010 = 7.5010 3 6 6 mol dm 6 mol dm 3 [PO4 ] = 22.5010 = 5.0010 3 = (7.5010 (5.0010 6 6 = 1.05(1.1)10 26 15 mol dm (e) (i) (enthalpy change) when 1 mole of an ionic compound is formed from its gaseous ions (ii) Mg has a smaller (ionic) radii than Ca 2+ 2+ OR Mg is smaller than Ca 2+ 2+ Total (a) (i) 2H2SO4 + HNO32HSO4 + NO2+ H3O + OR H2SO4 + HNO3 HSO4 + NO2 + H2OCambridge International Examinations 2014<br />
Page 7 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 41 (ii) any three of [4]curly arrow from inside the benzene ring to NO2 group intermediatepenalise NO2 connectivity or missing methyl group (once)curly arrow from C-H bond into ringproduct + H (or as diagram H allow 2- and 3-substituted nitromethylbenzene) PMT (b) (i) acidity of ClCH2CO2H > CH3CO2H AND (ClCH2CO2H) as an electronegative/electron withdrawing Cl (ii) acidity of phenol > CH3CH2OH AND electrons on oxygen (on phenol) delocalised into ring OR benzene ring withdraws electrons from oxygen stronger acid linked to weakening O-H bond/anion being stabilised [3]Cambridge International Examinations 2014<br />
Page 8 Mark Scheme Syllabus Paper Cambridge International A LevelOctober/November 2014 9701 41 PMT redox/reduction (electrophilic) substitution hydrolysis/ acid-base/ (c) Na Br2 NaOH ONa (or ionic) Br OH Br OH and OH or ionic ONa ONa OH [1] ONa 1 mark for each correct structure for reaction types, 2 correct = 1 mark, 3 correct = 2 marksCambridge International Examinations 2014 [6]<br />](https://learnah.org/wp-content/uploads/2018/08/November_2014_v1_MS_-_Paper_4_CIE_Chemistry_A-level_4-0.jpg)
