International Education

Cambridge
Cambridge Assessment Subsidiary and Advanced Level
International Cambridge International Advanced
AS & A Level

CANDIDATE
NAME
AbdelRakim Husham
CANDIDATE
CENTRE NUMBER
NUMBER
x
sZ0 9701/21
CHEMISTRY October/November 2019
9L.9 43/60
Paper 2 AS Level Structured Questions A 1 hour 15 minutes

6
z0 Candidates answer on the Question Paper.
Additional Materials: Data Booklet
bestexa
FIRST
READ THESE INSTRUCTIONS
you hand in.
candidate number and name on all the work
Write yOur centre number,
Write in dark blue or black pen.
diagrams or graphs.
Youmay use an HB pencil for any
clips, glue or correction fluid.
Do not use staples, paperBARCODES.
DO NOT WRITE IN ANY

Answer all questions.

Electronic calculators may be used. not use appropriate units.
lose marks if yOu do not show your working or if you do
You may
A Data Booklet is provided.
together.
fasten all yOur work securely
At the end of the examination, ]at the end of each question or part question.
in brackets [
The number of marks is given

printed pages and 1 blank page.

This document consists of 11

AE Carmbridge Assessment [Turn over

IB19 11 9701 21/FP International Education
UCLES 2019
 2

Answer all the questions in the spaces provided.

1 (a) Chlorine can be prepared using the following reaction.

MnO,(s) t 4HCI(aq) ’ MnCI,(aq) + 2H,0() + CI,(g)
() Explain why MnO,(s) is described as an oxidising agent in this reaction.

Refer to oxidation numbers in your answer.

.sAlorène.g....Getting....*died.from..to.O.
[1)

(ii) State what you would observe during this reaction.

Efferves. uences. [1]

(b) The halogens chlorine,bromine and iodine are allvolatile elements.

State and explain the trend in volatility down Group 17.

.Jalatlt...AeeSaea.don.. .....geup....1...sise....n9..f..electes. .......

...iosese...k..5e....Man.Der....Na....focces...insssae..
(3]

(c) Chlorine undergoes disproportionation during many chemical reactions.

() Write an equation for the reaction of chlorine with cold aqueous sodium hydroxide, NaOH.
Explain why it is a disproportionation reaction.
equation ...Clz.+.NaHaNa.cl.+Naclo.Aa.
explanation ..s.chloin..s..getbig.sidiisd.R.dacsd.
[2]
(i) One of the products of the reaction of chlorine with hot aqueous sodium hydroxide differs
from those in (c)(i).
Identify the compound that is formed in thisreaction that is different from that formed in the
reaction in (c)(i).
[1]

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 3

(d) State and explain the use of chlorine in water purification.

....4.<lO..to...k..nKo.D(Sminms.
(2)

(e) Under certain conditions,chlorine undergoes a free-radical substitution reaction with ethane.
(0) State the conditions required to initiate this reaction.

.QN.ight.
(ii) Write the overall equation for this free-radical substitution reaction.

SHe.tS,He.t.H,.. [1]

[Total: 12)

©UCLES 2019
9701/21/OIN/19 [Turn over
 2 (a) Complete the table to give details of the type of bonding and
Oxides of Period 3 structure shOwn by some of the
elements
Na,O MgO Al,0, SiO, SO,
boiling point/°C 1275 3670 2977 2950 45
nature of oxide basic basic amphoteric acidic acidic
bonding ionie ionic ionic covaleat covalent
structure
giant lattis gint lattic giant
lattike ggit es ole

(2]
(b) () Explain why the
boiling point of SiO, is much higher than the boiling point of
SO,
Siz...hes..many..st.fonqes..bands....as...a.cendt.. t. .sequres.
.hi_hel.ehecsy..ta. iSeak.thes..bonde.
(ii) Al,0, is an [3]
amphoteric oxide.
Explain what is meant by the term
answer.
amphoteric. Use chemical equations to
..Ace.. ...SthstNCes.. illustrate your
. . which.. .cescts.. .s.t..bat..9sd..a.ka..alkl
(iii) State what
youwould
observe when asmall sample of Na,O is placed in
[3)

. Sskd..sppea. water.
[1)

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 5

chemicalreactions to sulfur.
Selenium is a Group 16 elementwhich shows similar
(c)
form Sef,molecules.
() Selenium reacts with fluorine to
Predict the shape of a molecule of Sef
[1]
Octuhedral
(i) The most stable oxide of seleniumn is SeO,.
reaction one Se-O is
Gaseous SeO, reacts to form asolid polymer, as shown. In the
replaced bytwo Se-0 to form a polymer.

AH=-346 kJ mol1
Se
Se

The bond enthalpy of Se=O is 514 kJ mol!.

Use these datato calculate the bond enthalpy, in kJmoB-, of Se-O.

WSi4-2:-346

bond enthalpy of Se-0=...39.. ....... kJ mol

(i) Se0, shows similar chemical reactions to SO,.

Suggest an equation to show the reaction of SeO, with aqueous sodium hydroxide, NaOH.

...SeQtNaQH.Ho.+NagSeg
[Total: 13]

OUCLES 2019
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[Turn over
 6

3 Crude oil is a natural source of hvdrocarbons that are used as fuels.

(a) HydrOcarbons with low relative molecular mass, M, are used as fuels in industry, in the home
and for transport.

There is a high demand for the hydrocarbons with low M,

() Name the process by which long-chain hydrocarbons are broken down into shorter-chain
hydrocarbons.
Craching
(ii) Give one reason why hydrocarbons with low M, are suitable for use as fuels.

(in) Incomplete combustion of hydrocarbons can release carbon monoxide, Co, into the
atmosphere.
ite an equation for the formation of CO from the incomplete combustion of butene,
C,H
(1]

(w) ldentify an analytical technique that can be used to monitor the levels of CO in the
atmosphere.
Outline how this analytical technique maybe used to monitor the levels of CO.

.Iofrared.speatsssspy..t.opstiy..aekagtt.

(b) Thiophene, CH,S), is an organic compound that is found as a contaminant in crude oil.
(i) Construct the equation for the complete combustion of
thiophene, C,H,S().
Include state symbols in your answer.

(ii)
.cyky.tat)Laigt.HQey.t.ts"
Astudent carries out an
experiment determine to
enthalpy the change of combustion of
C,H,S().
Explain the meaning of the term enthalpy change of combustion.

. Eat..sbange.hen..ole..f.a. ndsbince.. mletel,.

...cambsts.

(2]

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 7

(ii) The student uses the following apparatus in the experiment.

thermometer

Copper container

water

-fuel burner
containing C,H,S()

mass of water in copper Container/g 200

initial temperature of water/°C 18.5

highest temperature of water/°C 37.5

Calculate the heat energy released, in J, by the reaction.

Assume that 4.18J of heat energy changes the temperature of 1.0cm° of water by 1.0°C.
Assume no heat is lost to the surroundings.

206y t i? (37.5 - i$-5)

heat energy released =

[21
(iv) The student used 0.63 g of C,H,S() in the experiment.

Calculate the enthalpy change of combustion of thiophene, AH(C,HS(0). Include a sign

in your answer.

AH(CH,S() = kJmo!
[2]
[Total: 13]
©UCLES 2019
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[Turn over
 (CH),CCHO is used in the synthesis of some antibiotics.
(a) (i) Give the name of (CH,),CCHO.

(i)
2:.2. sdimethy.. prspenal.
State the hybridisation of the carbon atom labelled with an asterisk, *
[1]

CH,
H,C-ç
CH,

...ap2. (1]

(b) TwO reaction sequences are shown.

CH,
H,C- NaBH, S
reaction 3
CH,

[O] reaction 1

A
T
(CH),CCO,H
reaction 2

() Reaction 1is an oxidation reaction.

ldentify the reagent(s) and conditions for reaction1.

siut...H, SOy.t.KzCrg.Qq,.it.heat.undec..sefle.

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 9
(ii) A,(CH),CCO,H, is a solid at room temperature.
B, CH,CO,(CH,),CH, is an isomer of A. B is a liquid at
room temperature.
Explain the difference in the physicalstates of A andB, with
forces that may exist. reference to any intermolecular

JE.ke. hydagn..bancing.. while..B....as..Sinple...Vaa

(3]
(iii) Give the balanced equation for the
reaction of (CH,),CCHO with NaBH, to form S
Use [H]to represent an atom of hydrogen
provided
by NaBH,

.(GH,)3caHO.+.H. »2(t).3<tOH.
(iv) Draw the structure of the organic
to form U. molecule T that reacts with A, (CH),CCO,H, in reaction 2,
(1]

Suggest a catalyst for reaction 2.

catalyst
(2]

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 10
(c) X, Y and Z are all isomers of
(CH,),CCHO.
Asummary of sonme of the reactions and properties of X, Y andZ is shown in the table.

compound observations with 2,4-DNPH observations with principal absorptions

Fehling's solution in infra-red spectrum

orange pt no reaction 1715cm

Y
red
pt red precipitate 1730 cm1

no reaction 3200-3600 cm 1
no reaction 1630 cm1
1050 cm
() Xand Yeach
contains a carbonyl group.
Complete the table with the expected observations for the
2,4-DNPH. reactions of X and Y with
[1]
(0) ldentify the functional group present in Y that causes the
Fehling's solution. recorded observation with

.A.dehyde.
(ii) Yhas a chiral centre and [1]
exists as a pair of optical
isomers.
State what is meant by the term
chiral centre.
..Scacha.saton. hsh..is..konded.te....t.di:ffexent..&ton. ....Sr.
"gfosp.ct.stoms..
(iv) Draw the optical
isomers of Y using the conventional
three-dimensional representation.
CH,

Hco CH

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 11

Z, CH,0, has a branched carbon chain. It shows geometrical isomerism.

(v) Complete the table with the bond responsible for each of the principal absorptions seen in
the infra-red spectrum of Z.

principal absorptions bond responsible

in infra-red spectrum
3200-3600 cm Ro -4

1630 cm C=C

1050 cm C-0

(vi) Draw the skeletal formula of Z.

H

Hc C-O4
[3]

(vii) Xcontains a carbonyl group. Xreacts with HCNDin the presence of a small amount of
NaCN, to form (C,H),c(OH)CN as shown.
X + HCN ’ C,H),C(oH)CN
Draw the mechanism of the reaction of X with HCN.

Draw the structure of X and the intermediate.

Include allcharges, partial charges, lone pairs and curly arrows.

HO

NC
C,Hs

3)

(vi) Statethe role of NaCN in the reaction in (c)(vii).

[1]
[Total: 22]

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