C L 3 6 Cambridge Chemistry Challenge Lower 6th June 2015 Marking scheme for teachers (please also read the additional instructions) p4 p5 p6 p7 Total 16 12 13 6 10 3 60 p2 mark p3 Page 1 1(a) (i) from mercury(II) oxide: 2HgO (ii) leave blank equations (underline reduced element): 2Hg + O2 2 from silver(I) carbonate: 2Ag2CO3 4Ag + 2CO2 + O2 2 (iii) from potassium nitrate(V): 2KNO3 2KNO2 + O2 2 (iv) from sulfuric acid and manganese(IV) oxide: 2H2SO4 + 2MnO2 2MnSO4 + 2H2O + O2 [ Half quantities accepted. 1 mark for equation; 1 for underlined ] 1(b) dot & cross diagrams [could be swapped ] × ×× × O ×× C × ×× O ×O×× 2– O ×× B × ×× O ×O×× ×× × × ×× (i) formula = CO3 × ×× × ×× × × ×× 3– (ii) formula = BO3 2 2 2 × ×× × O ×× ×× ×× ×× O O ×× ×× ×× O neutral compound isoelectronic with nitrate(III) ion: ozone [also allow CF2, difluorocarbene, or O=N–F, nitrosyl fluoride] formula: O3 2 (iii) formula = O4 1(c) name: 2 Page total 16 Page 2 1(d) leave blank activation energy for puckered-ring O4 from O2: = 480.0 – 89.3 + 48.7 = 439.4 kJ mol–1 Ea pinwheel O2 89.3 48.7 480.0 puckered ring O2 4 [2 marks if worked out standard enthalpy of formation of puckeredring O2 = 390.7 kJ mol–1] Ea O2 1(e) A= 16O + 2 + C = 16O218O2 B= 18O + 2 1 [1 mark if all three correct] 1(f) tick the shape(s) most consistent with the data: 3 [1 mark each; lose 1 mark for any wrong (down to zero)] 1(g) time taken: k.e. of O4 molecule = 4.00 keV = 4000 × 1.602 × 10–19 J k.e. = ½ m v2 ∴v= = 6.408 × 10–16 J 2 × (k.e.) m mass of 18O4 = 18.00 × 4 g mol–1 ≡ 18.00 × 4 6.022 × 1023 × 103 = 1.1956 × 10–25 kg v= kg molecule–1 4 2 × 6.408 × 10–16 = 103 500 m s–1 1.1956 × 10–25 time of flight = 0.100 m 103 500 m s–1 = 9.66 × 10–7 s (≈ 0.1 µs) [lose 1 mark each time a power of ten is incorrectly used] Page total 12 Page 3 2(a) i) zero ii) leave blank 3, 5 4 iii) iv) 4, 6, 9 1, 8 [zero marks for part containing missing / additional wrong answers] 2(b) circle one or more: Free radical Nucleophilic Electrophilic Substitution 2 Addition [–1 mark for any wrong down to zero] 2(c) three alkenes: 3 2(d) i) 13, 16 ii) 14, 18 4 iii) iv) 12, 18 16, 17 [zero marks for part containing missing / additional wrong answers] Page total 13 Page 4 2(e) leave blank for α-terpineol i) connect: & d j [only structure of B+ required no labels on it needed] ii) Carbocation B+: f i e d j A f i e j c a d b B a for borneol i) connect: c & ii) Carbocation C+: a [only structure of C+ required no labels on it needed] a g c cyclisation d f g b c e e j f i b g 2 d j i h B h 2(g) cyclisation c b 2(f) 2 h g h g C for β-pinene c i) connect: & i ii) Carbocation D+: a c g h a cyclisation d e f b [only structure of D+ required no labels on it needed] e j i B f g b c d e d j i h D f c 2 a b j i g h Page total 6 Page 5 leave blank 2(h) Cation U+: 1 O H H 2(i) 2(j) connections: [only connections required -1 mark for any incorrect a down to zero] b h c j i g u d s f V k l e t r q to k m o q also allowed n instead of t to k p c to g l to f j t to k u s H H o q c g l n b h i k t r a m d f H 3 e W p Compound X O H H H [1 mark for enol] 3 H H OH H Compound Y H O H 3 H H O H O Page total 10 Page 6 2(j) leave blank Anion Z– O H O H or H H H O O H H O O H 3 [ either structure fine ] Page total 3 Page 7