2010 JC2 H2 Preliminary Examination Paper 2 Suggested Solution

1 The graph below shows the first eight successive ionisation energies of X
against the order of removal of electrons.

Comment [YUN1]: Somestudents

failtoidentifylargeenergydifference
(a) From the graph, deduce which group of the periodic table does element X [2] rd th
betweenthe3 and4 electronand
belongs to. th
evenmentionthatthelargestIEisthe4
IE,whichisincorrect.
Removing the 4th valence electron requires a vast amount of energy./
Comment [YUN2]: Studentswere
There is a large jump from the 3rd to 4th IE. th
notclearinmentioningthatthe4
electronwereremovedfromaninner
The 4th electron is removed from an inner shell / There are 3 valence shell.Somementionedthatitwas
removedfromadifferentelectronshell
electrons. ortherewasachangeinshell.Needto
bemorespecific.
Therefore, element X is from group III. Comment [YUN3]: Manystudents
(b) Given that element X is from period 3, identify element X. [1] writeGroup3insteadofGroupIII.Group
no.shouldbewritteninRomannumeral.
X is aluminium. Somestudentswerenotabletointerpret
thedataanddeducethecorrectgroup.
(c) Write a balanced chemical equation for the formation of the oxide of [3]
Comment [YUN4]: Moststudents
element X and by means of balanced equations, indicate whether the wereabletoidentifyXasaluminium.
oxide reacts with aqueous NaOH and HCl (aq). Studentswhohadidentifythewrong
groupwouldnotbeabletoidentifythe
4 Al (s) + 3 O2 (g) 2 Al2O3 (s) correctelement.Inaddition,smallgroup
ofstudentsdeducethewronggroupbut
It undergoes neutralisation with both acids and bases to form salt abletoidentifyX,thisshowsthatthereis
and water. lackofunderstandingofthequestion
andnotabletolinkthepartsofthe
question.
Al2O3 (s) + 6 HCl(aq) 2 AlCl3(aq) + 3 H2O (l)
Al2O3(s) +2NaOH(aq)+ 3H2O(l) 2Na[Al (OH)4] (aq) Comment [YUN5]: Moststudents
werenotabletogivethecorrect
(d) Write a balanced chemical equation for the formation of the [1] productsofthereactionofXwith
sodiumhydroxide.Manystudentsalso
chloride of element X. failtowritebalancedequations.Some
2 Al (s) + 3 Cl2 (g) Al2Cl6 (s) or Al (s) + 3/2 Cl2 AlCl3 studentsalsoleftouttheequationon
theformationoftheoxide.
Comment [YUN6]: Moststudents
(e) Explain the reactions of the chloride of element X with water. Include all [3] wereabletogettheequation.Quitea
relevant equations. numberofstudentswritetheequation
AlCl3 undergoes hydrolysis to give an acidic solution (pH 3). asAl+3HClAlCl3+3/2H2whichis
wrongasthequestionisaskingfor
The high charge density of Al3+ ion polarises one of its surrounding formationofthechloridefromthe
water molecules hence weakening the O-H bond which results in the elements.
release of a proton: Comment [YUN7]: Manystudents
AlCl3 (s) + 6H2O(l) [Al(H2O)6]3+ (aq) + 3Cl- (aq) didnotexplainthereactionorgave
incompleteanswersforthereactionof
[Al(H2O)6]3+ (aq) [Al(H2O)5(OH)]2+ (aq) + H+ (aq) thechloridewithwater.Mostwereable
togivethecorrectequations.Some
studentsdidnotgavebalanced
equations.
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 (f) Explain whether X or the element below X in the same group will have [2]
higher first ionization energy.
Electrons are added to the next valence shell.
The distance between the nucleus and the valence electrons
increases.
Decrease in electrostatic forces of attraction between the nucleus Comment [YUN8]: Moststudents
and valence electrons. wereabletoexplainthisquestion.Some
studentsgaveincompleteanswer
Less energy needed to remove the valence electron, thus 1st I.E. withoutexplainingthatelectrostatic
decreases. forcesofattractiondecreases.Prefer
Element X will have a higher first ionization energy. answertodiscussdistanceand
electrostaticforcesofattractioninstead
ofshieldingeffectandeffectivenuclear
charge.Somestudentswerealsonot
Total: 12 marks abletoexplainthetrendofIEdownthe
group.Anumberofstudentsmisreadthe
questionanddiscussabouttheelement
aboveX.

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2 Stearic acid is present in animal fats and glucose is present in animal glycogen. The
enthalpy change of combustion data of these two compounds are shown in the table
below.

Compound Stearic acid, C18H36O2 (s) Glucose, C6H12O6 (s)

-1
Hc / kJ mol -11400 -2810

(a) By comparing the enthalpies of combustion, comment on the fact that [1]
arctic animals store their energy mainly in the form of fats, whereas
tropical animals store their energy mainly in the form of glycogen.
Arctic animals need more energy against the cold as stearic acid can
release more heat upon metabolism.

(b) By considering the number of lone and bond pair of electrons, draw the [4]
Lewis structure and predict the general shapes of the following
molecules or ions
(i) F2O
2 bond pair and 2 lone pair bent

(ii) H3O+
3 bond pair and 1 lone pair Trigonal pyramidal

(c) Architectural and other models are often made from brass (an alloy of
copper and zinc).
The process of making a brass window frame is as followed:
1. The pattern of a window frame is drawn on the brass using a
special ink.
2. The unprotected brass (not covered by ink) is removed by using
dilute hydrochloric acid and the outline of the frame remains.

(i) With the aid of the Data Booklet, identify the metal that dissolves in [3]
dilute hydrochloric acid. Explain your answer.
Zn2+ + 2e Zn -0.76 V (Eoxd)
Cu2+ + 2e Cu +0.34 V (Eoxd)
H+ + 2e H2 0.00V (Ered)

For HCl, H+ undergoes reduction.

ZZX H E = 0.00V
2H+ + 2e YZZ 2

For Copper, it undergoes oxidation.

ZZX
YZZ
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 Cu2+ + 2e Cu E = +0.34V
Ecell = 0.00 0.34 = -0.34 V
Ecell < 0, thus Cu will not dissolves in acid.

For Zinc, it undergoes oxidation.

Zn2+ + 2e YZZ ZZX Zn E = -0.76V

Ecell = 0.00 (-0.76) = +0.76 V

Ecell > 0, thus Zn will dissolve in acid.

Zinc metal will dissolve in dilute hydrochloric acid.

(d) A heart pacemaker consisting of zinc and platinum electrodes, is
implanted into the body tissues. These electrodes in the oxygen-
containing body fluid, with a pH of 7.4, form a cell in which zinc is
oxidised and oxygen is reduced.
(i) Write a balanced equation for the overall reaction that takes place [1]
when a current flows.
Anode: Zn Zn2+ + 2e
Cathode: O2 + 2H2O + 4e 4OH-
Overall:
2Zn + O2 + 2H2O 2Zn2+ + 4OH-
OR
2Zn + O2 + 2H2O 2Zn(OH)2
(ii) How would the Ecell value change if a human with the heart pacemaker [3]
undergoes a period of intense exercise? Explain your answer.
Ecell value will increase.

During exercising, lactic acid is produced. Thus, it results in the

decrease of the pH.

When pH drops, [H+] increases, thus the equilibrium position in

O2 + 2H2O + 4e YZ ZZXZ 4OH
-

shifts to the right, favouring reduction. (as OH- is neutralised by H+)

Therefore, E value will become more positive and Ecell value will
increase.

Total: 12 marks

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3 (a) To extract titanium from its ore rutile, TiO2, the ore is first mixed with coke
and the mixture was reacted with chlorine at 800oC to 1000oC. The reaction
yield titanium (IV) chloride gas and carbon monoxide gas.

The next step is the reduction of the chloride by magnesium under a blanket
of noble gas. The reduction temperature is at about 850oC to 900oC and a
spongy mass of titanium is obtained and the magnesium chloride is tapped
off from time to time and recycled.

Substance Melting point (oC)

Titanium (IV) chloride -24.8
Titanium oxide 1843
Magnesium 650
Magnesium chloride 714

(i) Using the data and information given, construct the chemical equations, [2]
with state symbols, of the above mentioned procedure.

TiO2 (s) + 2C (s) + 2Cl2 (g) TiCl4 (g) + 2CO (g)

TiCl4 (g) + 2Mg (l) Ti (s) + 2MgCl2 (l) Comment [YUN9]: Moststudents
wrotestatesymbolswronglyasthey
failedtotakethemeltingpointsgiven
intoconsideration.

(ii) Hence, using the equations, determine the mass of rutile required to [1]
produce 100 g of titanium metal.

100
Amt of Ti= = 2.088mol
47.9
TiTiO2
Mass of TiO2 required = 2.088 x (47.9 + 16 + 16) = 167 g Comment [YUN10]: Moststudents
wereabletoscorefullmarkforthis
question.
(b) Briefly relate the rate of SN2 reaction of CH3Br with the CH3O- and CH3CO2- [2]
nucleophiles.
For CH3O-, negative charge on O is not delocalised and it gets
intensified as it is bonded to electron donating CH3 group. Hence,
electrons is readily available at O and rate of reaction with CH3Br will be
faster.

For CH3COO-, negative charge on O is dispersed via charge

delocalisation. Hence, electrons is less available and rate of reaction
with CH3Br is slower. Comment [YUN11]:
Somestudentsdescribedthe
nucleophilicsubstitutionmechanism
(c) Outline possible synthesis for each of the following compounds from the [4] whichwasnotrequiredbytheqn.
Someexplainedusingsterichindrance
given starting materials. whichisnotapplicableascarbonnois
(i) CH3CH2COOH to CH3CH2CH2CN thesame.
Comparisonshouldbemadewrtthe
negativechargeonoxygenandnot+on
carbon.

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 CH3CH2COOH CH3CH2CH2OH CH3CH2CH2Br

LiAlH4 in dry ether HBr alcoholic
r.t.p heat KCN,
heat

CH3CH2CH2CN Comment [YUN12]:
Commonmisconception:thereisno
(ii) CH3CH2CH2OH to CH3CH2CH(OH)CO2H singlesteptoconvertOHtoCN.
RtpconditionforLiAlH4commonly
missedout.Heat/refluxcantbeused.
CH3CH2CH2OH CH3CH2CHO HCN, NaCN, 10-20oC
+
K2Cr2O7/H
distillation CH3CH2CH(OH)CN

dilute H+/heat

CH3CH2CH(OH)CO2H Comment [YUN13]:
Somestudentsusedfreeradical
(d) Suggest methods by which the following compounds could be distinguished substitutionwhichisnotrecommended.
from each other using chemical tests. The chemical tests may rely on a Oxidationofprimaryalcoholto
aldehydemustbedoneusingK2Cr2O7and
preliminary break-up of the compounds and subsequent testing of the notKMnO4
reaction products. ForHCN,ifNaOHisused,(aq)mustbe
[3] stated.
(i)
CH3CH2CH2 CHO COCH2CH2CH3
and
Test: Add Tollens reagent and warm

CH3CH2CH2 CHO
: Silver mirror is observed.
Comment [YUN14]:
COCH2CH2CH3 Testusedmustbecorrectinorderto
scoremarksforobservations.
: No silver mirror is observed Heat/refluxnotacceptedforTollens
(ii) test.
O O ManystudentsusedFehlingstest(no
aliphaticaldehydepresent)/2,4DNPH
O O (bothreact)whichcantwork.
and
Test: Add hot sodium hydroxide followed by aqueous iodine.
Or hot acid followed by alkaline aqueous iodine

O
O
:Brown iodine decolourises, yellow ppt observed
Comment [YUN15]:
O Testmustbecorrecttogainmarksfor
observations.
O Hydrolysisofestermustbedonefirst
:No decolourisation, no yellow ppt observed usingheat/refluxbeforeiodoformtest
couldbeused.
Oxidationtestcantbeusedafter
hydrolysisasbothalcoholscanbe
oxidisedtoformketones.

Total: 12 marks
4 (a) Draw the organic product(s) of each reaction carried out on compound X.

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 O
Compound X Br
N
H

CH2Br

Aqueous Acidified KMnO4,
NaOH, heat Heat

[4]

Comment [m16]: Needtoconsider

NaOH, Heat: basichydrolysisfirst,followedby
neutralisationofacidicfunctionalgroups.

O
C
O-Na+

H2N Br
CH2OH
and
Comment [m17]: Needtoconsider
Acidified KMnO4, Heat: oxidationofalkenesandalkylbenzene,
followedbyacidichydrolysisofesters
andamides.Thebasicaminethatis
COOH producedmustbeneutralisedtoo.

H3N+ Br
COOH and

(b) The diagram below shows a segment of a polypeptide chain Y of a protein.

H2
C
O H O H2C CH2 H H
C C N C C N C C N
H H H O CH2SH

(i) A strand of polypeptide chain would continue to fold further into [2]
structural pattern of alpha-helix or beta-pleated sheets to gain extra
Page7of15

 stability.
Using a clearly labelled diagram, describe the alpha-helix structure.

Comment [m18]: Makesurethatthe

Omusthave2LONEPAIRS!

Hydrogen bonds are formed between O atom of (-C=O) group

and the H atom of (-N-H) group.
(ii) Explain why the polypeptide chain Y given in the question will not coil [1]
into an alpha helix structure.
There is no H-atom on the N atom (of the cyclic amide) available for H-
bonding with the O atom of C=O of the fourth peptide on the backbone
chain. Or the cyclic structure interfere with the hydrogen

(c) Interpret each of the following observation as fully as you can. Use
diagram or equation(s) in your interpretation if applicable.
(i) The relative molecular mass of ethanoic acid in benzene is 120, but [3]
measurement of the density of the vapour is consistent with a relative
molecular mass of 60.
In benzene, ethanoic acid forms dimers. Comment [m19]: Nocreditswillbe
awardedforspellingerror.

+ Comment [m20]: Lonepairof

electronsmustbedrawnpointing
O H O towardsH.
C CH3 +andmustbeclearlyindicatedon
CH3 C allinvolvedhydrogenbondingspecies.
O H O
+

In vapour form, the acids exists as monomer as sufficient energy has

overcome the hydrogen bonds between 2 ethanoic acid molecules Comment [m21]: Indicationto
energymustbeshownclearly.Thebig
differenceintermsofintermolecular
(ii) The pH of the end-point in the titration of ethanoic acid with sodium [2] distanceisaaconsequenceofthe
hydroxide is greater than 7. energythatispresentwhichresultsin
CH3COO-Na+ CH3COO- + Na+ thebreakingoftheintermolecular
hydrogenbond.
CH3COO- + H2O CH3COOH + OH-
Comment [m22]: Studentsmustbe
Salt hydrolysis occurs
awarethatthisistheendpointofthe
[H+] is lesser than [OH-] reaction.Thus,neutralisationhasalready
End point pH is greater than 7. beencompleted.
Total: 12 marks

5 (a) Vitamins are essential organic molecules that are essential to the well being

Page8of15

 of our human health. Four vitamin molecules are given below:

OH

Vitamin A

H
N O
S
HO O N
H

Vitamin B7

CH2

Vitamin D3
HO

Vitamin K3
O
[2]
(i) State one reagent and condition that will react with vitamin A and not
with vitamin K3 and describe what would be observed.

Reagent: acidified potassium dichromate (VI), OR K2Cr2O7/H+ (aq),

heat/reflux

Observation: orange solution turns green

(ii) State one reagent and condition, other than oxidising agents that will
react with vitamin D3 and not with vitamin B7 and describe what would
be observed.

Reagent: Br2 (aq), r.t.p

Observation: decolourisation of reddish brown bromine

Page9of15

 (b) Draw the structural formulae of each of the organic products when the [3]
stated vitamins are treated with the following reagents.

(i) vitamin B7 reacts with hot sulfuric acid

NH3+
S
HO O NH3+ SO42-

dontpenaliseifnoSO42

(i) vitamin K3 reacts with 2,4-dinitrophenylhydrazine

O 2N

O 2N N N N N NO2
H H
NO2

(ii) vitamin D3 reacts with hot acidified potassium manganate (VII)

O
O

O and
O

(c) Heating a 5 carbon alcohol A with concentrated sulfuric acid gives a [4]
compound B. When an aqueous halogen-containing solution is added
to B, compound C having a molecular mass of 120.5 is produced.
Subsequent addition of alcoholic NaCN to C following by hot aqueous
sulfuric acid results in the formation of 2-
hydroxycyclopentanecarboxylic acid.

(i) Draw a structural formula for each of the organic compounds A, B and
C.
Cl

OH OH
A: B: C:

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 (ii) Suggest a possible structural formula when hot concentrated sulfuric

acid is added to 2-hydroxycyclopentanecarboxylic acid.
O
C
O
O
C
O

(d) Vitamin C is useful in the prevention of scurvy. It is a reducing agent and can [2]
be widely found in green leafy vegetables.

OH OH
HO O O HO O O
+ 2 H+ + 2 e

HO OH O O
vitamin C

The enthalpy change of reaction for the above reaction is +420 kJ mol-1

Explain why vitamin C will lose its reducing property when the green leafy
vegetables are subjected to prolonged heating in boiling water.

Reaction is endothermic. Thus, in boiling water, temperature is high. In order

to reduce the temperature, by Le Chateliers Principle, the position of
equilibrium will shift to the right, favouring the endothermic reaction. This
favours the oxidation process. Thus, Vitamin C will lose its reducing
property.

Total: 12 marks

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6 The literature value of standard enthalpy change of neutralisation is

H+ (aq) + OH- (aq) H2O (l) HOneutralisation = 57.4 kJ mol-1

This is only applicable to the neutralisation between strong acids (eg. HCl (aq)) and
strong bases (eg. NaOH (aq)).

However, standard enthalpy change of neutralisation involving weak acids or weak

bases deviates from the value 57.4 kJ mol-1. The reason for the deviation is due
to the energy required for the dissociation of the weak acids or weak bases. Unlike
strong acids and bases, weak acids and bases do not completely dissociate in
aqueous solution. Taking ethanoic acid for example, the solution of ethanoic acid is
in equilibrium between the undissociated ethanoic acid molecules and the
dissociated hydrogen ions and ethanoate ions.

CH3COOH (aq) H+ (aq) + CH3COO- (aq) HO1

You are to design an experiment in which the heat evolved from neutralisation of
known amounts of ethanoic acid and sodium hydroxide is determined.

CH3COOH (aq) + NaOH (aq) CH3COO-Na+ (aq) + H2O (l) HO2

From the data collected and using Hess Law, determine the enthalpy change of
dissociation of ethanoic acid, HO1.

Chemicals provided:

FA1 1 mol dm-3 of ethanoic acid

FA2 1 mol dm-3 of sodium hydroxide
(a) Draw an enthalpy cycle diagram that show the relationship between
HOneutralisation , HO1 and HO2. [1]

H o2
CH3COOH (aq) + NaOH (aq) CH3COO-Na+ (aq) + H2O (l)

H o1 H oneutralisation

CH3COO- (aq) + H+ (aq) + NaOH (aq)

(b) You may use common apparatus found in the school laboratory for this
experiment. Outline all the steps, in the correct order, that you would take to
determine the enthalpy change of neutralisation between FA 1 and FA 2,
HO2. You need to consider the following:

choice of material for the calorimeter

calibration of calorimeter
appropriate amounts of FA1 and FA2 used in the experiments
appropriate way of determine the temperature difference of the
experiment
[5]

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 Calibration of Calorimeter
1. Use a -10 to 100oC thermometer, measure the temperature of the cold
water. If it is greater than 10 C, add a little ice to it and stir until its
temperature is about 10 C.
2. Use the 100 cm3 measuring cylinder to transfer a 50.0 cm3 portion of
cold water into a 100cm3 beaker. Use a Bunsen burner, heat the beaker
carefully and gently, with stirring, until the temperature of the water in it
has been increased by about 35-40 C.
3. Use a 100 cm3 measuring cylinder to transfer a second portion of 50.0
cm3 of cold water into your Styrofoam cup. Place the cup in a beaker to
prevent it tipping over.
4. Stir the cold water in the calorimeter with the thermometer, measure and
record its temperature (Tcold).
5. Stir the hot water in the beaker, measure and record its temperature
(Thot).
6. Immediately, add the hot water from the beaker to the cold water in the
calorimeter, stir, measure and record the temperature of the combined
water (Tcombined).
7. Empty your calorimeter, dry all apparatus using the paper towel and
allow them to return to room temperature.

Actual Experiment involving FA1 & FA2

1. Use a 100 cm3 measuring cylinder to transfer 50 cm3 of FA 1 the calibrated
styrofoam calorimeter. Place the cup in a beaker to prevent it tipping over.

2. Stir the FA 1 in the calorimeter with the thermometer and measure its
temperature. Record the temperature, Tinitial,1.

3. Use another 100 cm3 measuring cylinder and measure a 50 cm3 portion of
FA 2 and transfer it into a beaker. Stir the FA 2 in the beaker with the
thermometer, measure and record its temperature, Tinitial,2.

4. Pour FA 2 from the beaker into to Styrofoam calorimeter. Stir the mixture
with a thermometer, measure and record the highest temperature
reached, Tmax.

Markers Comments:

(i) Have to indicate apparatus used

Styrofoam cup (with lid)
(50-ml or 100-ml) measuring cylinder to measure volume
(-10 to 100oC) thermometer to measure temperature
(250-ml glass beakers (to prepare ice water and to heat up water)
(Bunsen burner, tripod stand with wire gauze)

(ii) Correct choices of temperatures for cold water and hot water for
calibration that will obtain a combined temperature of 25oC to 30oC upon
mixing.
Tcold less or equal 10oC
Thot Tcold = 35oC to 40oC or 40oC to 45oC

Page13of15

 Markers Comments (Continuation):

(iii) Appropriate volume used

80 to 120 cm3
and equal volumes of cold and hot water
Vol of FA1 and FA2 used must be same as in calibration
(note that in calibration, we are calibrating the surface of the
Styrofoam cup (that would come into contact with the reagents)
using water. Hence the volume of FA1 and FA2 used in actual
experiment used must be the same.)

(iv) Stirring whenever there is mixing before taking temperature

(v) Measurements of all the necessary temperature

Calibration: Thot, Tcold and Tcombined
Actual experiment: Tinitial, Tmax
Have to use back the calibrated cup when performing the
experiment involving FA1 & FA2. (Otherwise, that defeats the
purpose of doing calibration!)

(c) Explain by calculation, how you would process your experimental results in
part (b) to determine the values of heat capacity of the calorimeter, enthalpy
change of neutralisation, HO2 and enthalpy change of dissociation of
ethanoic acid, HO1 respectively. [4]
Qwarm water = ( Qcold water + Qcalorimeter )

(mcT )warm water = [(mcT )cold water + (Ccalorimeter T)]

For HO2,

Calculate amount of water (in mole) formed

Calculate Q using

Q = mcombined solution of FA1 and FA2c(Tmax Tinitial) + Ccalorimeter(Tmax Tinitial)

HO1 = HO2 HOneu

(d) Identify one major source of error or limitation in the experiment in part (b)
and discuss its impact on the accuracy of the results obtained. [1]

Any one of the following:

Heat lost to the surrounding AND possible discussion to impact:
Tmax measured is lower than expected. (Lower HO2 obtained.)
Lower Q calculated. Lower HO2 obtained.

Temperature readings are not precise enough as the thermometer used

can only measure up to 0.2oC. This cause Q (and hence HO2 ) calculated
to be inaccurate.

Volume readings are not precise enough as the measuring cylinder used
can only measure up to 0.5 cm3. This cause Q (and hence HO2 )
calculated to be inaccurate.
Page14of15

 (e) Suggest one possible modification that would minimize this error or limitation.
Explain how your modification would improve the accuracy of the results [1]
obtained.

Any one of the following, but must be related to error stated in part (d)
Conduct in a draught free room to reduce heat lost.
Increase precision the temperature readings by using thermometer of
0.1oC instead of 0.2oC.
Change from a measuring cylinder to burette (up to 0.05cm3) or pipette
(up to 0.1cm3) for more precise volume measurements.

END

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