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2A10-AL GHEM

PAPER
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HONG KONG EXAMINATIONS AND ASSESSMENT AUTHORITY HONG KONG ADVANCED LEVEL EXAMINATION 2O1O

CHEMISTRY A.LEVEL PAPER Question-Answer Book
8.30 am - 11.30 arn (3 hours) This paper rnust be answered in English
1.

Candidate Number
1

Marker's
Use Only Marker No.

Examiner's Use Only
Examiner No.

There are THREE sections in this paper, Section A, Section B and Section C.
Section A carries 60 marks, Section B carries 2A marks, and Section C carries 2A marks.

2.

A1

A2 A3

3.

Answer ALL questions in Sections A and B, and ONE question in Section C. Some constants, characteristic infra-red absorption wavenumber ranges, standard reduction potentials and a Periodic Table can be found on pages 19 and 20 of this Question-Answer Book.
:

4.

A4 A5
A6
A Total

lnstructions for Sections A and B
5.

After the announcement

the examination, you should first write your Candidate Number in the space provided on page 1 of this

of the start of

Question-Answer Book, and stick barcode labels in the spaces indicated on pages 1, 3, 5, 7 and 9.
6

Write your answers in the spaces provided in this Question-Answer Book. Do not write in the margins. Answers written in the margins will not be marked.
Supplementary answer sheets will be supplied on

B7 B8

7.

request. Write your Candidate Number, mark the
question number box and stick a barcode label on each sheet, and fasten them with string INSIDE this
book.
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B

Total

No extra time will be given to candidates for sticking the barcode labels or filling in the question number boxes after the 'Time is up' announcement.

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Hong Kong Examinations and Assessment Authority All Rights Reserved 2A10
20IO.AL.CHEM

SECTION A

Answer ALL questions. Write your answers in the spaces provided'

l.

(a)

(i)

Provide a piece ofevidence for the wave nature ofelectrons'

(iD

For each of the following orbitals, sketch its pictorial representation and indicate the
location of the atomic nucleus in your diagram.
s

orbital

p orbital
-o
J4
L

-cj

()
cd

() d
L. l-.

J4 *{
L.

)-.

-o

c)

-o
{-)
Li

0)

{-)

o
F
u)

o
B
a bo k

t-.

bo
S{
CB

F

(3

cB

marks)

tr
(l)
+-)

()
{-)
l-.
e4

(b)

A student made the following remark:
()

C) +-l
L<

,The rate of an elementary gaseous reaction increases with temperature because the
kinetic energy of the reactant molecules increases with temperature.'

average

{-)
L..

F
u-)

a

k

L<

c)

c)

a

Is the explanation provided by the student regarding the increase in reaction rate appropriate
Elaborate Your answer.

?

F a
)-.

(3
Answers written in the margins

marks)

will not be marked.

2OIO.AL-CHEM I_2

2

m

) F a B ct) Answers written in the margins will not be marked. cB )< -: () o € {-. I {-) () (4 marks) c) . L{ C. c) Electrical conducting property under room temperature and atmospheric pressure . o l-. 1. (c) Complete the table below by inserting relevant information of silicon and lead.v t-.l-) l-{ (n l. 2OIO. oo :) 5) {-) f-.AL-CHEM I_3 .Please stick the barcode label here. both of which are Group IV elements: Silicon Lead Electronic configuration of an atom in ground state Type E C) L l-. Cd of bonding in solid state J4 -o +-) L.) ld cS ?1 L.< F B u) $-{ c) c. C) x - o Fa F B cn I a bo r< CS Chemical formula(e) of chloride(s) Li L.

XeF+ and XeFo . (6 Answers written in the margins marks) will not be marked.r-t l-{ u) = L 0. 2OIO-AL-CHEM I-4 4 . It reacts with fluorine forming a range of compounds including XeF2. (D Draw the three-dimensional structure of each of the following molecules: XeF2 XeFa 'o 6) J4 cd L.2.) +) F (n ?1 Lr a) . l-r o tr s +. ?1 (iii) Suggest why the compounds formed between xenon and chlorine are unstable.) (ii) Suggest why XeF3 does not exist. but forms unstable compounds with chlorine. l-. € (l) J4 L (€ (u L -o {rl c. l-. a L a0 3 l-a c L{ bo $< d )r x c) rf-a 5) +) ii o ?a c) . (a) Xenon is a noble gas.t-) +) L{ F a tr c) F a F.) Lr o F CA L{ GI L.

c. 2. Each aliquot was titrated with 0. several 20. (b) From a saturated aqueous solution of calcium hydroxide. 20IO-AL.0 cm'aliquots of the solution were withdravvn. Calculate (i) the concentration of hydroxide ions in the saturated solution.100 mol dm-3 hydrochloric acid using suitable a indicator. and '(.v L cg l-. q) J L Cg . l-. The mean titre was 9. bo L1 d F c) +-) |) L{ Cr) +) +-) C) a.) d (l) F -o +-l F c) -o l-r o +) o 3 l< bo f{ F Cg 3 cn tt) (iD the solubility product of calcium hydroxide at the temperature of the experiment. *-.CHEM I-5 T l prg" rotrj i .Please stick the barcode label here. 3 CN F t{ () B (t) CA ! q) 3 t-r CN (4 marks) Answers written in the margins will not be marked.) +) +-.10 cm3.

O *') l-. r23I tt'I is chemically more reactive thant2\. (a) Answer the following multiple-choice questions. D. I27I. c.) Answer and L{ v) 3 () 3 a tz'I a t{ c) are two isotopes of iodine. c) {-) x L. q.3. has a greater proton-to-neutron ratio than The number of 26 hours. B. ? Which of the following statements about these two isotopes is/are conect (l) (2) (3) A. o F u) t1 B cn bo t< 63 )-. l23I atoms in a sample drops to % of its original value after (l) only (2) only (l) and (3) only (2) and (3) only Answer (4 marks) Answers written in the margins will not be marked. 6 20IO. D. Which of the following compounds of titanium does not exist under room temperature and atmospheric pressure ? cg Lr L{ q) . B. D. (i) Which of the following processes is endothermic ? A. +-J () t{ B l< +-) A. B. (iD freezing of water condensation of steam reaction of H*(aq) with Otf(aq) to give HzO(l) electrolysis of water Answer Which of the transition metals below does its ground-state atom have an unpaired electron in an s orbital ? ro L Cg )< H A. (iv) r23I TiO2 bo t< tx l< (d CB TiCl3 K2Tio4 K3TiF6 C) *) t< a) +j {-. D. C.O +r () (iiD o : F1 Titanium has the ground-state electronic configuration: lsz 2s2 2p6 3s2 3p6 3dz 4s2 .) J4 . C. B. C. chromium manganese iron cobalt Answer : (l) € Jl t.AL-CHEM I_6 . r23I is radioactive with a half-life of 13 hours U) t- F while r27I is not radioactive.

m . and account observation with the aid of chemical equation(s). and then excess FeSOa(aq) to the resulting solution E a) t-.) t< q) F a :i F a (6 marks) Answers written in the margins will not be marked. F {-. L.Please stick the barcode label here.l-) L{ (ii) adding NH3(aq) dropwise to CuSOo(aq) until in excess a) +J t'r L< B ct) 3 u) c. CS !q) Jl L< cs F< tr -o +=.o {r} o B ct) *r o F F a *-i bo Cg bo - L. (b) State the expected observation in each of the following experiments.1 cs q) {-J C) () . 0) o . for the (i) adding excess HzSO+(aq) to K2CrOa(aq). zOIO-AL-CHEM 1_7 7 . 3.

. 20IO-AL-CHEM 1_8 .8l I kJ mol (i) : . bo cd F Lr bo L{ L.) +. /\ HOOC -r LHr* HH \l C:C COOH D a tr (.p .) {-) +J l< > U) *< c) F cn l-. Answers written in the margins will not be marked.p.7gL kJ mol -r Explain why the melting point of D is lower than that of B. Compound A is an isomer of dimethyl fumarate.) F 3 a 302oC m. L.) -o {-) -o I c) o 3 o F CA U) Lr l-. dimethyl fumarate m. HOOC H --. *-{ (b) Both dimethyl fumarate and A can be hydrolysed to their corresponding dicarboxylic acids. However. € JI t< l< F C) CB (.4. cd F Explain why the melting point of A is lower than that of dimethyl fumarate. l02oc -l goc (a) (i) Name the type of isomerism involved. (iD E c) JI f-. cB € (1 C) o) (3 marks) +) (. 130oC LHru _ . Dimethyl fumarate can be found in most leather products since it is commonly used as a mould inhibitor.p. B and D. it was banned in Europe for all kinds of consumer goods in March 2009 because it was found to cause skin allergies. The structures and melting points of these two compounds are given below: cH?ooc \l C:C /\ H COOCH3 H HH \t C:C /\ cH3ooc coocH3 A m.p. c.\ / C:C /\ COOH H B m.

() {-) l-.) U) f-.) o t4 B bo Cd (4 U) marks) t- bo l-i CB ll-r C) !) (c) D can be converted to B by heating it with concenhated HCl.Please stick the barcode label here. 9 20IO-AL-CHEM 1_9 i T pug" rotrr I . C) l< l. 3 a l..{ () lJ L. (b) (ii) Explainwhythe Al1rs of Bismore negativethanthatofD.{ 3 (. 4. 0) F CA l- E a (3 marks) Answers written in the margins will not be marked. J4 a.) E c) J4 t(d E c) d ll-1 t< -o L € o F u) -o +J 0. Propose a mechanism for the conversion.

NHCH3 E ketamine (i) Give the systematic name of E. . is 1 {-. € -v ${ d F C) CS -o I C) o cn (II) Give the reaction conditions required for the above synthesis. what is/are the organic Explain the formation of the side product(s).r C) ]-) c) L a r< () B F cl) Sr (. (6 marks) Answers written in the margins will not be marked.) (ii) E o) J4 L. 10 20I0-AL-CHEM l-10 . (a) Ketamine is a drug which has a wide range of effects in human including analgesics and anaesthesia.) 3 u) > v) (II) Suggest ONE way to suppress the formation of the side product(s).o o F ct) 0. (a (D Suggest what F is.5.) 3 bo Lr L e0 L 6d CC (1 F F (. F. "tp as prefix is '2-chlorophenyl-' .) () ts) (- t{ (iii) (r) If the mole ratio of E and F used in the synthesis side product(s) ? :1. Ketamine can be synthesised from compound E by treating it with reagent F. (Hint: The name for the substituen.

J Lr |) .r o 3 () +J tr 3 ct) cn *-.r-) l. -o () |) o B V) -o c) CI halofenozide *-l o e4 -{ 3 (n Lr (€ bI What are the reagen(s) synthesis ? and conditions represented by each of G.) C) 1< F '{-r G: *. 20I0-AL-CHEM 1-l l 11 . l< a) a) l-. L. (b) Halofenozide is an insecticide commonly used for white grub control. from 2-methylpropene and methylbenzene as outlined below: G (cHr)z c:cHz-------> 2-methylpropene It can be synthesised (cHr)rccl H2NNH2> (cHs):cNHNH2 CH: cHg ----+ methylbenzene J CH: -*K L __-+> CI o 'ci Jd F fr-N/c(cH3)3 H 0) Lr cS KL --*---+> (cH:):GNHNH2 room temperature 'o C) J4 fr CS l-.5. J. 3 a J: B a K: L: (4 marks) Answers written in the rnargins will not be marked. K and L in the above )-a b0 t-'r tr H cd e1 Lr c.

6. c) +-) l< ti V) F CN L< 0) 3 V) C) 3 v) (ii) Explain why [emim]BFa has low vapour pressure. [emim]*. and at least one of them is a bulky organic ion. generally have low vapour pressure and low They are becoming popular solvents in organic synthesis. Draw structure(s) to show the dispersion of charge in [emim]*. J4 t< CC 1l L{ -: () 0) )-. including [emim]BFa. Ionic liquids mainly consist of ions. This enables them to meet the particular requirements of a synthesis. They are called 'room-temperature ionic liquids'. l-Ethyl-3-methylimidazolium tetrafluoroborate ([emim]BFa) is an example of ionic liquids. is stabilised by dispersion of its positive charge. (a) E (l) ll t< Cg 1-Ethyl-3-methylimidazolium cation. Answers written in the margins will not be marked. -o +) i. ---Nr. melting point. are liquid at room temperature.o o |) o F (n F a L{ cs F bo oo (1 mark) d F c) i. (b) (D () o) l< Some ionic liquids. Read the passage below and answer the questions that follow: Ionic Liquids Non-aqueous ionic liquids.zi-[emim]* t BF+- Ionic liquids are also described as 'designer solvents' because their properties such as melting point viscosity and hydrophobicity can be modified by changing the structure of their component ions. or simply ionic liquids. T2 2010-AL-CHEM t-12 . Account for the low melting point of such ionic liquids.t c) .

viscosity ? (5 marks) as (c) Suggest THREE advantages of using ionic liquids over using organic solvents such CH3COCH3 and (C2H5)2O in organic synthesis.) (.) -o {-) o 3 o l-.6. B a q) $-. E o) J4 L E.) +-l () (3 +r marks) t-.a (1 mark) END OF SECTION A Answers written in the margins will not be marked. G L l< tr c) q) t-. (c lr J t< c. Explain your answer.r B oo l-{ CS ao l-. a a l. 2010-AL-CHEM l-13 13 T i prg" rotrr i . c. (b) (iiD Replacing the ethyl group in [emim]BFa by a butyl group gives another ionic liquid lbmim]BFa. in organic F rt) L. B a (d) Suggest ONE reason which prevents ionic liquids from replacing organic solvents synthesis. l-( c) L{ q) L a. Which of these two ionic liquids would you expect to have a higher Explain.) cS )-. L{ -o !) F.

SECTION B Answer 7.) () a Sketch a graph to show the variation of the measured physical parameter with the volume of H2SOa(aq) added.: x--r Ba(OH)r(aq) magnet () -o :r o d magnetic o 3 cn stirrer F a bo L{ lCC (D What physical parameter of the reaction mixture is measured by this set-up ? uo li c'd H t-. Explain your answer. (a) The diagram below shows the set-up of a titrimetric experiment involving the following reaction: Ba(OH)r(aq) + H2SOo(aq) --> BaSOa(s) + zHzO(t) H2SO4(aq) measuring device Ei (. ALL questions. Write your answers in the spaces provided. T4 20IO-AL-CHEM r-14 . +..) r< l-{ -: JL -I * rJ1 -In C) (c (s F () -o LJ {-) C--3r-r LI. l- (ii) H2SOa(aq) is added gradually to Ba(OH)r(aq) until in excess. tr B a G) 3 V) (3 marks) Answers written in the margins will not be marked. () a) +-) C) 0) cn li .

o B t{ (g ts c.) {-) Lr B C') o 3 a t-. hardness in the sample. 15 2010-AL-CHEM t-15 i T p"g" rot"l I .) bo (4 (c) The hardness of a water sample is due to Caz*(aq) ions.o {-) o B a l-r C) -o l-{ +-. ct) marks) bo k Cd Outline a method for determining the L{ L.) F Cn I (3 marks) Answers written in the margins will not be marked. (i) the use of an air condenser instead of a water condenser in reflux (ii) the use of concentrated H3PO4 instead of concentrated H2SO4 in the preparation of hydrogen halides from the corresponding sodium halides ro () J4 lr c!0 -o J4 o F tr () -a r< rS .7. (b) State under what circumstances each of the following practices would be aaopteO ana exptain your answel. € L o c *) F tt) r< c) +. {-) (1 l< C) l-. (.

Acetanilide (N-phenylethanamide) can be synthesised from aniline (phenylamine) according following reaction scheme: to the H ry aniline NHz I W HCI> r. inject 1. to (a) Suggest why it is necessary to convert aniline to its hydrochloride salt in Step 1. B L c) (A B a t< c) E c/) (1 mark) 3 a t-.8. E () {-) c) C) +j t< {-) l-.y L q) (€ Lr t-{ J t< a) Cg L< -o I L- c) (. Collect the crude product by suction filtration.06 g of CHgCOONa(s) in 6 cm3 of distilled water) into the reaction mixture. (c) Would acetanilide be obtained in good yield ethanoic anhydride ? if sodium ethanoate solution is added before Explain. Immediately after the injection.0 Step j: g of aniline in a mixture of 27 cm3 of water and 0.) -o {-) o o 3 a L{ (l (b) ethanoic anhydride in Step 2.yNH3*cl- (t)(cH3co)2o (2)cH3coo-Na* \) > ry*-r:" cHr acetanilide The procedures of the experiment are summarised below: Step Step l: 2: Dissolve 1. mark) a L.i cd C) {rJ 3 ! bo Explain why sodium ethanoate solution has to be added immediately after the injection of bo CB ?1 l-.24 cm3 of ethanoic anhydride into the solution obtained in Step I. (2 Answers written in the margins marks) will not be marked.9 cm3 of concentrated hydrochloric acid. add sodium ethanoate solution (prepared by dissolving 1. . T6 20I0-AL-CHEM l-16 . Using a dry syringe.

Outline the experimental procedures for thl-purification of the crude product by recrystallisation from an etlanol-water mixture. Pure acetanilide is a white solid. 2010-AL-CHEM I -r7 T7 l ) l P.8. However.< U) 3 c) L F a (3 (0 Suggest a method to veri$r whether or not the recrystallised sample of acetanilide is pure.r () rO {-) o o B a L{ F cn bo cd Lr oo d F )ri t-r q) {-) () +. (d) Draw a labelled diagram of the assembly of apparatus used in the suction ftltration in.ge rotal T I . |) lr o 0) +J 3 CN L V) c) r. the crude product obtained appears yellow due to the presence of impurities. marks) (l END OF SECTION B mark) Answers written in the margins will not be marked. () CS (l) -o +.v l-< )-. to .Sr"pT (2 marks) (e) o J fi ad >< '(.

I and II of the Periodic Table covering their (20 marks) 10.SECTION C Answer ONE question. ? Discuss the usefulness of synthetic polymers in daily life and the fend (20 marks) BND OF PAPER 2010-AL-CHEM 1-18 18 . 9. Marks will be allocated approximately as follows: chemical knowledge organisation 50% 30% 20o/o presentation(includinguseoflanguage) Use equations. Write an essay on the chemistry of the elements in Groups bonding and solid state structures. The examiners are looking for the ability to analyse. Write your answers in the AL(D) Answer Book. What are synthetic polymers of their development. to evaluate and to express ideas. reactivity and uses. diagrams and examples where appropriate.

I8 J gt K-t Characteristic Infra-red Absorption Wavenumber Ranges (Stretching modes) Bond Compound type Alkenes Wavenumber range /cm-l 1610 1680 C:C to 1680 to 1800 c:o C=C Aldehydes.3.00 x 108 m s-t Ionic product of water at 298 K. phenols (hydrogen-bonded) Amines o-H C_H 2500 to 3300 2840 to 3095 3230 to 3670 3350 to 3500 o-H N-H 20IO-AL-CHEM I -19 I9 .02 x 1023 mol-l Avogadro const ant.6. carboxylic acids and derivatives Alkynes 2070 to 2250 2200 to 2280 C=N Nitriles Acids (hydro gen-bonded) Alkanes. Specific he Kr: 1.R . L Planckconstant. alkenes.8.Constants Gas constant. ketones.00 x 10-l a mo|z dm-6 at capactty of water : 4. c .63 x 10-3aJs Speed of light in vacuum.31 J K-l mol-l . h-6. arenes Alcohols.

0 Pa (23 1) U 238.40 +0.91 -0.50 ZCr3*(aq) + 7H2O(0 +1.34 2H2O({) +0.Cr(s) Zn(s) Cr(s) Fe(s) Cr2*(aq) V'*(uq) Pb(s) Hz(g) Cu*(aq) Cu(s) SOz(g) + -3.0 126 9 8s Au t97 .68 +0.9 87 138.9 13 111 J5 Tc : Ru 'Rh i98r lr-t1 1 1'-11 9 n.0 Np (237) Pu Q44\ Am (243\ Cm t747 ) BK Cf Qsr Fm Md (258) No Lr (260 ) Q47\ (252) (257) Qs9\ 20I0-AL-CHEM I -20 20 .0 T7 202 18 t2 Mg 24.3 20 Ca 40..1 Pb za7 2 Po At (210) Q0e) Rn Q22\ Fr Q23\ Ra Q26\ Ac Q27\ Db Q62\ 60 61 58 Ce 62 63 6+ 65 66 67 68 69 70 7l Lu 175.13 0. 16 Pd 270 30 31 28.23 +1.0 103 Pr 1 Nd 144.87 Au(s) 2F-(aq) Periodic Table atomic number GROUP 2 He I J 1 II 4 5 III 6 IV 7 V N 14.3 100 Tm 168 9 101 Yb r73 0 102 140 90 140.6 Y 889 Zr 72 9t2 178.6 50 Sn 118 82 "29 CU Zn 65.15 +0.56 +0.9 91 r45) r57 96 93 158.33 Au(s) Mn2*(aq) ZHzO(t) +1.5 35 lSe "94 52 Br 799 53 Kr 838 54 i06 -8 Pt I Ag 107.9 99 Es Er 167.5 98 Ho 164.5 104 IIo 959 56 Cs Ba r37 88 .47 + 4H2O(l) +1.5 55 Sr 87 .19 -1 .87 -2.66 * e- Oz(g)+2H*(aq)+2eFe3*(aq) + e- -1.Standard Reduction Potentials at 298 K Esr v VO2*(aq)+ZH*(aq)+eOzG) + zHzO(!) + 4eCu*(aq) + eIz(s) + 2eMnO+-(aq) aor v Li.51 +1. Ti 47 .18 -0.0 19 Si CI 1 Ar 40.36 +1.0 Hg 200.04 -2.7 49 535 11 1t 33 As 749 51 32 134 35.77 +0.76 -0 .8 81 Sb 121 Te 8 I Xe 131 86 3 r27 .6 TI 204 1 195.(aq) + eK.0 16 S 8 40 l0 Ne F 19.3 Lt 89 57* ** i1 \1' 183 9 Hf Rf (26r) 59 Ta 180 9 105 r32.44 -0.07 Mn2*(aq) + ZHzO(t) +1 .2 92 Pm ( Sm 150 4 94 Eu 152 0 95 Gd Tb 3 Dy 162.0 VI VII 9 Li 6.23 +1.r 32 Ge 72.00 +0.54 +0.7 4 -0.71 -2.41 -0. I 38 1i AI l5 P 3 1.0 B relative atomic mass 10 8 C 12.0 36 2l Sc 22 23 K 39. Ot Ir 186l ii90l i9ll \h 558 58 9 28 \i 58.69 +2.9 73 Rb 85.52 +0.38 -1.9 97 Th 232.9 ll Be 9.80 +1.9 v 24 25 Cr 520 42 Mn 549 26 Fe 27 Co l 450 39 509 37 40 4l Nb 92.34 +0.0 Na 23.00 2Br-(aq) 2HzO(!) 2Cl-(aq) pb2*(aq) + HzO(t) +l .6 84 8i Bi 209.17 q) + 2e- = = = = + = = = = = = = = + = + = + = V'*(uq) + HzO(/) aOH-(aq) Cu(s) 2l-(aq) MnOa2-(aq) H2O2(aq) Fe2*(aq) Ag(s) VO2*(aq) + +0.92 -2.(aq) * eCat*(uq) + 2eNa*(aq) + eMgt*(u q) + 2eAl3*(aq) + 3eMn2*(a q) + 2eVt*(uq) + 2eCr2*(aq) + 2eZnz*(aq) + 2eCr3*(aq) + 3 eFe2*(aq) + 2e- Cr3-(aq) + e- V'*(uq) + ePb2*(aq) + 2eZH*(aq) + 2eCu2*(aq) + eSoo2-(aq) + 4H*(aq) + 2eCu2*(a Li(s) K(s) Ca(s) Na(s) Mg(s) Al(s) Mn(s) V(s) .9 79 Cd 80 ll2 In 4 114.0 14 o 16.26 Ag*(uq) + e- VOr*(aq)+2H*(aq)+eBr2(l) + 2eMnO2(s) + 4H*(aq) +2e- Oz(g)+4H*(aq)+ 4eCr2O72-(aq) + 14H*(aq) + 6eClr(g) + 2ePbO2(s)+4H*(uq) +2eAu3*(aq) + 3 e+ 8H*(aq) + 5eMnOa-(aq) Au*(aq) + eFz(g) + 2e- -0.4 48 Ga 69.