D Its formation requires the use of cyanide ions as a catalyst.

8
21
26 How many moles of oxygen molecules are needed forreact
In the presence of ultraviolet light, ethane and chlorine to give a mixture
the complete of products.
combustion of one mole of
20 Diesters can be made from diacids such as propane-1,3-dioic acid, HO2CCH2CO2H.
3-methylpent-2-ene?
ALKANES WS 1
Which compound could be present in the mixture of products?
Which
A 9 combination of B reactants
9 21 would form
C the18 diester CH3CH D 2OCOCH
19 2CH2CO2CH2CH3?
A CH3Cl
A butane-1,4-dioic acid and ethanol SECTION A
B CH3CH2CH2Cl
271 The
B ethanedioic C17 Hand
hydrocarbonacid 36 can be cracked.
propan-1-ol
C CH3CH2CH2CH3
C ethanedioic
Which compoundacid,
is theethanol and butan-1-ol
least likely to be produced in this reaction?
D CH3CH2CH2CH2CH3

D C
A propane-1,3-dioic
3H 8 B acid,
C4 Hethanol
8
and Cpropan-1-ol
C8 H16 D C16 H34
[S‘14 11 Q27]
22 Compound X produces a carboxylic acid when heated under reflux with acidified potassium
2 dichromate(
21
28 In the presence
Compound VI of ultraviolet
X ).has
Compound Xlight,
has no
the molecular ethane and
reaction
formula Hchlorine
C4 with react
sodium to give a mixture of products.
metal.
10 O2 . X has an unbranched carbon chain and
contains two OH groups.
Whichcould
What compound
be the could beofpresent
identity compoundin the
X?mixture of products?
On reaction with an excess of hot, acidified, aqueous manganate(VII) ions, X is converted into a
A CH3Cl of molecular formula C H O .
A propanal
compound 4 6 4

B
B propanone
CH3CH2CH2Cl
To which two carbon atoms in the chain of X are the two OH groups attached?
C
C propan-1-ol
CH3CH2CH2CH3
A 1st and 2nd
D
D propan-2-ol
CH3CH2CH2CH2CH3
B 1st and 3rd

[S‘14 13 Q21]
C 1st and 4th
3 Which
23
22 Compoundmolecule could anot
X produces be obtained
carboxylic from heated
acid when the cracking of a with
under reflux molecule of potassium
acidified nonane,
CH
D 3(CH
2nd2)and
dichromate(7CH 3?
3rd
VI ). Compound X has no reaction with sodium metal.
A CH
What 2=CHCH=CH
could 2
be the identity of compound X?
B CH3CH2CH2CH2CH3
A propanal
C CH3CH2CH2CH2CH2CH=CH2
B propanone
© UCLES
D 2014 9701/11/M/J/14

(CH3CH2CH2)3CH
C propan-1-ol 11 [S‘14 13 Q23]
D propan-2-ol
4 The free radical substitution reaction between methane and chlorine involves initiation,
30
propagation and termination stages.
23 Which molecule could not be obtained from the cracking of a molecule of nonane,
Which
CH3(CHrow is correct?
2)7CH3?

A CH2=CHCH=CH
involved2in radical produced in
initiation stage a propagation stage
B CH3CH2CH2CH2CH3
C A CH3CHheterolytic fission
2CH2CH2CH2CH=CH2
H•
© UCLESB2014 heterolytic fission 9701/13/M/J/14
CH 3•
D (CH3CH2CH2)3CH
C homolytic fission H•
D homolytic fission CH3•

[S‘14 13 Q30]

© UCLES 2014 9701/13/M/J/14

CEDAR COLLEGE 109 ALKANES WS 1

 acid produced?

A CH2 O B CH4 O C C2 H4 O D C 3 H 6 O2

5 Which equation correctly represents the balanced equation for the complete combustion of a
29
hydrocarbon with the formula CxHy?

y y
A CxHy + (x + )O2 → xCO2 + H2 O
2 2

y
B CxHy + (x + )O2 → xCO2 + yH2 O
4

y y
C CxHy + (x + )O2 → xCO2 + H2 O
4 4

y y
D CxHy + (x + )O2 → xCO2 + H2 O
4 2

11
[W‘14 11 Q29]

6 The citrus flavour of lemons is due to the compound limonene, present in both the peel and the
29
juice.

limonene
© UCLES 2014 9701/11/O/N/14 [Turn over
What is the mole ratio of carbon dioxide to water produced when limonene is completely burnt in
oxygen?

number of moles number of moles

carbon dioxide water

A 4 3
B 5 4
C 5 8
D 9 7

[S‘15 11 Q29]

30 What is the organic product when ethanamide, CH3CONH2, is boiled with excess aqueous
sodium hydroxide?

A CH3CN
B CH3CO2–NH4+
C CH3CONH–Na+
D CH3CO2–Na+

CEDAR COLLEGE 110 ALKANES WS 1

 8

7 Crude oil is a mixture of many hydrocarbons ranging in size from 1 to 40 carbon atoms per
22
molecule. The alkanes in crude oil can be separated because they have different boiling points.

The table below shows the boiling points of some alkanes.

boiling point
alkane Mr
/ °C

butane 0 58
pentane 36 72
7
hexane 69 86
20 Compound Y is treated with an excess of hydrogen
2-methylbutane 28 gas in the presence
72 of a nickel catalyst. The
product is fully saturated.
dimethylpropane 10 72
2,3-dimethylbutane 58 86

What is the correct explanation for the difference in the boiling points of the three isomers with
Mr = 72?

A Boiling point is dependent upon the length of the carbon chain only .
compound Y
B Increased branching on a carbon chain increases the boiling point.
What is the number
C Increased of chiral
branching carbonthe
reduces atoms in the
strength of product?
the intermolecular hydrogen bonding.
A 5Increased branching
B 6reduces the strength
C 7 of the intermolecular
D 8 van der Waals’ forces.
D

[W‘15 11 Q22]

21
8 Which
23 equation
Compound represents
Q contains a double
three valid propagation
bonds per step in the chlorination of ethane?
molecule.

A C2H6 + Cl • → C2H5Cl + H• O O
Y
B H4ClX• CH
C2H5Cl + Cl • → C2CH + HClCH C CH2 C OH
2 2

C C2H5Cl + H• → C2H5• + HCl

Q
D C2H5• + Cl • → C2H5Cl
Which bond, X or Y, will be ruptured by hot, concentrated acidified KMnO4 and how many [J'18 12lone
Q21]
pairs of electrons are present in one molecule of Q?
22 Maleic acid is used in the food industry and for stabilising drugs. It is the cis-isomer of butenedioic
acid and has the structural formula HO2CCH=CHCO2H.
bond ruptured by hot, number of
What is the product formed from the reaction of maleic acid with cold, dilute, acidified
concentrated acidified KMnO4 lone pairs
manganate(
A VII) ions?X 5
A B HO2CCH(OH)CH(OH)CO
X 2H 6
B C HO2CCO2H Y 5
C D HO2CCH2CH(OH)CO
Y 2H 6
D HO2CCOCOCO2H

23 Primary halogenoalkanes undergo hydrolysis reactions.

Which reaction would occur most rapidly if they are all warmed to the same temperature?

A 2015
© UCLES C2H5Br with H2O 9701/11/O/N/15

B C2H5Br with NaOH(aq)

C C2H5Cl with H2O
D C2H5Cl with NaOH(aq)
CEDAR COLLEGE 111 ALKANES WS 1
 For each
2 Hof are
the
2SO 4 questions
+ CO3 → COonly
in this + are
2section,
H2O one only
or 4more
+ SO of are
the three numberedisstatements 1 to 3 may
be correct. correct correct correct correct
3 H2SO4 + MgO → MgSO4 + H2O
Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against
No other combination of statements is used as a correct response.
the statements that you consider to be correct).
SECTION B
35 Silver chloride dissolves in aqueous ammonia.
Use
The of the DataABooklet
responses may be
to D should be appropriate
selected on for
thesome
basisquestions.
of
What happens in this process?

31 In
1 2011 A international
an
Ammonia groupBwith
forms a complex the Ag+ ion.
of scientists agreedC to add two new elements
D to the Periodic
Table. Both elements had been made artificially and are called flerovium, Fl, and livermorium, Lv.
1, 2 and 3acts as a Brønsted-Lowry
2 Ammonia 1 and 2 base. 2 and 3 1 only
are only are only are is
correctreaction occurs.correct
3 A redox Fl
correct Lv correct
proton number 114 116
No
1 other
36 A carcombination of statements
has a catalytic converter is used
fitted toas
itsaexhaust.
correct response.
On analysis its exhaust gases are shown to
contain small quantities of nucleon
nitrogen number
oxides. 289 292

⑧
Use of the Data Booklet may be appropriate for some questions.
From
Whichthe informationwould
modifications about result
atomsininlower
the table, which
exhaust statements are
concentrations correct?oxides?
of nitrogen

31 1Which
1 One atom ofin
anstatements
increase Lv hassurface
about
the one more
areaneutron
the atoms 23
ofNa and
the than
24 one atom of Fl.
Mg are
catalyst correct?
in the converter
2–
212 One
They Fl
haveion
an increase thehas
in the
same
the same
number
rate number
of flow theofexhaust
ofoffilled electrons
electron as one
orbitals.
gases atomthe
through of Lv.
converter
+
323 One
TheyLv ionthe
have hassame
the same number
number of electrons
ofofcombustion
neutrons. one Fl – ion.
in theasengine
a much higher temperature

[J‘14 12 Q36]
3 They are both reducing agents.
32
2 The
37 chlorine
Which oxide
alcohols free be
cannot radical, Cl O•, to
dehydrated is form
produced by the reaction between chlorine atoms and
alkenes?
ozone.
32 Which
1 CHcompounds
3OH contain covalent bonds?
Cl • + O3 → Cl O• + O2
12 aluminium
(CH3)3COHchloride

⑧
Which
CHfeatures
23 ammonia
3CH2OH
are present in the chlorine oxide free radical?

13 an odd number
calcium fluoride of electrons
2 a single covalent bond
33 3Ethylene glycol,
a dative HOCH
covalent 2CH2from
bond OH, oxygen
is used to
aschlorine
a de-icer. It allows ice to melt at temperatures below
0 °C.
[N'17 12 Q32]

Which statements are correct?

1 Ethylene glycol changes the extensive network of hydrogen bonds in ice.

2 Ethylene glycol molecules form hydrogen bonds with other ethylene glycol molecules.
3 2017
© UCLES Ethylene glycol molecules will dissolve in the water formed from the ice.
9701/12/O/N/17 [Turn over

© UCLES 2014 9701/12/M/J/14 [Turn over

© UCLES 2017 9701/13/M/J/17 [Turn over

CEDAR COLLEGE 112 ALKANES WS 1

 2

Answer all the questions in the spaces provided.

ALKANES WS 2
1 1 (a) Define the term mole.

....................................................................................................................................................

.............................................................................................................................................. [1]

(b) 10 cm3 of a gaseous hydrocarbon, CxHy, was reacted with 100 cm3 of oxygen gas, an excess.

The final volume of the gaseous mixture was 95 cm3.

This gaseous mixture was treated with concentrated, aqueous sodium hydroxide to absorb the
carbon dioxide present. This reduced the gas volume to 75 cm3.

All gas volumes were measured at 298 K and 100 kPa.

(i) Write an equation for the reaction between sodium hydroxide and carbon dioxide.

....................................................................................................................................... [1]

(ii) Calculate the volume of carbon dioxide produced by the combustion of the hydrocarbon.

volume of CO2 produced = ................. cm3 [1]

(iii) Calculate the volume of oxygen used up in the reaction with the hydrocarbon.

volume of O2 used = ................. cm3 [1]

(iv) Use your answers to (b)(ii) and (b)(iii), together with the initial volume of hydrocarbon, to
balance the equation below.

............CxHy + ............O2 ............CO2 + zH2O [2]

(v) Deduce the values of x, y and z in the equation in (iv).

x = .............................

y = .............................

z = .............................
[3]
[S‘14 23 Q1]

© UCLES 2014 9701/23/M/J/14

CEDAR COLLEGE 113 ALKANES WS 2

 6

32 Ethane reacts with chlorine to form chloroethane.

C2H6(g) + Cl 2(g) C2H5Cl (g) + HCl (g)

(a) (i) Use bond energies from the Data Booklet to calculate the enthalpy change for this reaction.
Include a sign in your answer.

enthalpy change = ................................. kJ mol–1 [3]

(ii) State the conditions needed for this reaction to occur.

....................................................................................................................................... [1]

(iii) Use a series of equations to describe the mechanism of this reaction including the names
of each stage and an indication of how butane can be produced as a minor by-product.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [5]

(b) Chloroethane can be converted back into ethane by a two-stage process via an intermediate
compound, X.

reaction 1 reaction 2
C2H5Cl X C 2H 6

(i) Give the name of X.

....................................................................................................................................... [1]

(ii) Suggest the reagent and conditions needed for reaction 1.

....................................................................................................................................... [2]

(iii) Suggest the reagent and conditions needed for reaction 2.

....................................................................................................................................... [1]
[S‘15 22 Q3]
[Total: 13]

© UCLES 2015 9701/22/M/J/15

CEDAR COLLEGE 114 ALKANES WS 2

 6

33 Heptane, C7H16, is an undesirable component of petrol as it burns explosively causing ‘knocking’ in

an engine.

(a) There are nine structural isomers with the formula C7H16, only two of which contain chiral
centres.

(i) Explain the meanings of the terms structural isomers and chiral.

structural isomers ...............................................................................................................

.............................................................................................................................................

.............................................................................................................................................

chiral ...................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................
[2]

(ii) Give the structures and names of the two structural isomers of C7H16 which contain a chiral
centre.

[4]

(b) (i) Write an equation for the complete combustion of heptane.

....................................................................................................................................... [1]

(ii) Write an equation for the incomplete combustion of heptane leading to the production of a
solid pollutant.

....................................................................................................................................... [1]

(iii) Incomplete combustion can also lead to emission of unburnt hydrocarbons.

State one environmental consequence of this.

....................................................................................................................................... [1]

© UCLES 2015 9701/21/O/N/15

CEDAR COLLEGE 115 ALKANES WS 2

 7

(c) The reaction of heptane with chlorine in the presence of UV light produces a wide variety of
products.

Formation of the monochloroheptanes can be represented by the following equation.

C7H16 + Cl 2 → C7H15Cl + HCl

(i) Name the mechanism of the reaction between heptane and chlorine in the presence of
UV light.

....................................................................................................................................... [1]

(ii) Describe this mechanism, using suitable equations and including the names of each stage
in the process.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [5]
[W‘15 21 Q3]

[Total: 15]

© UCLES 2015 9701/21/O/N/15 [Turn over

CEDAR COLLEGE 116 ALKANES WS 2

 6

34 Crude oil is a mixture of hydrocarbons and provides many useful chemicals when processed.

Two of the stages involved in the processing of crude oil are fractional distillation and cracking.

(a)

fraction A

fraction B

fraction C

fraction D

fraction E
crude oil in

fraction F

(i) What has to be done to the crude oil before it enters the column?

....................................................................................................................................... [1]

(ii) What trend in structure is there from fraction A to fraction F?

.............................................................................................................................................

....................................................................................................................................... [1]

(iii) State the trends in two properties of the fractions from A to F.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]

(b) The naphtha fraction from fractional distillation of crude oil is used as a starting material for
cracking.

(i) Write an equation for the cracking of C12H26 to form the products ethene and one other
hydrocarbon in a 2 : 1 mole ratio.

....................................................................................................................................... [1]

© UCLES 2016 9701/23/M/J/16

CEDAR COLLEGE 117 ALKANES WS 2

 7

(ii) Suggest a use for each of the products from your equation in (i). Explain what makes each
product from (i) suitable for the use you suggest.

use of ethene ......................................................................................................................

.............................................................................................................................................

explanation .........................................................................................................................

.............................................................................................................................................

use of other product ............................................................................................................

.............................................................................................................................................

explanation .........................................................................................................................

.............................................................................................................................................
[4]

(c) Burning hydrocarbons can cause a number of environmental problems.

The products of internal combustion engines can include oxides of nitrogen and oxides of
carbon.

Sulfur dioxide is a by-product of burning coal in power stations.

(i) Explain how and why oxides of nitrogen are produced in internal combustion engines.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]

(ii) Write an equation for the reaction between nitrogen monoxide and carbon monoxide in a
catalytic converter.

....................................................................................................................................... [1]

(iii) Write equations to show the involvement of nitrogen monoxide in the formation of acid rain
from atmospheric sulfur dioxide.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [3]

(iv) Describe two of the problems associated with acid rain.

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]
[S‘16 23 Q3]
[Total: 17]

© UCLES 2016 9701/23/M/J/16 [Turn over

CEDAR COLLEGE 118 ALKANES WS 2

 8

45 (a) The hydrocarbons A, C4H10, and B, C4H8, are both unbranched.

A does not decolourise bromine.

B decolourises bromine and shows geometrical isomerism.

(i) Draw the skeletal formula of A.

A
[1]

(ii) The hydrocarbon A, C4H10, has a branched isomer.

A has a higher boiling point than its branched isomer.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]
[S‘17 22 Q4]
(iii) Give the structural formula of B.

....................................................................................................................................... [1]

(iv) Explain why B shows geometrical isomerism.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

....................................................................................................................................... [2]

© UCLES 2017 9701/22/M/J/17

CEDAR COLLEGE 119 ALKANES WS 2

 10

46

Cl
reaction 1 reaction 2

(a) Reaction 1

(i) 1 to occur.

.......................................................................................................................................

(ii) 1.

reaction

Initiation
................................. Cl 2 2Cl •

•
propagation + Cl • + HCl
..............................

Cl
•
Propagation
................................. + Cl 2 + Cl •

Cl
• a
+ Cl • ti
..............................

(b) 2.
Elimination
..............................................................................................................................................
[M’18 22 Q4]

© UCLES 2018 9701/22/F/M/18

CEDAR COLLEGE 120 ALKANES WS 2

 6

27 Crude oil is a complex mixture of hydrocarbon molecules.

The hydrocarbon molecules in crude oil are separated by fractional distillation. Fractional distillation
is used because the different hydrocarbon molecules in crude oil have different boiling points.

(a) Explain why the hydrocarbon molecules in crude oil have different boiling points.
Different hydrocarbons have different
....................................................................................................................................................
no of electrons .

....................................................................................................................................................
.

....................................................................................................................................................
in of
Resulting different strengths
....................................................................................................................................................
'

Vander Waals forces .

....................................................................................................................................................

....................................................................................................................................................

.............................................................................................................................................. [2]

(b) Some of the hydrocarbon molecules obtained from crude oil are processed further by cracking.

Suggest why some hydrocarbon molecules are processed further by cracking.

....................................................................................................................................................
Produces more useful alkanes I Alkenes
....................................................................................................................................................

.............................................................................................................................................. [1]
6 [J'18 21 Q2]

38 (c) Cracking one mole of dodecane, C12H26, produces two moles of ethene and one mole of another
hydrocarbon molecule.
(a) (i)
(i) Write the equation for this cracking reaction.
Combustion
....................................................................................................................................... [1]

(ii)
The ethene can be used in the production of poly(ethene). (a)(i).
Cf HH t 124202 →
8002 t 9h20
(ii) .......................................................................................................................................
Give the full name of the process used to produce poly(ethene) from ethene. [2]

....................................................................................................................................... [1]
(b) not

(i)

cracking
....................................................................................................................................... [1]
.

[J'18 22 Q3]

3 3 .

(ii)
© UCLES 2018 9701/21/M/J/18

CEDAR COLLEGE 121 ALKANES WS 2

[2]
 correct.
H 7 3
CH CH3
1 In the radioactive decayCof an isotope CH
of leadCto anOH
isotope of bismuth, a particle 0 is emitted.
D enthalpy
17 The standard CH OH
changes of formation of HCl and HI are CH–92 C OH
kJ mol –1X
–1 and +26 kJ mol–1
3 3 3
respectively.
Which particle is –10 X? H ALKANES WS 3
H CH3
Which statement is most important in explaining this difference?
A electron SECTION A
A
211 B Chlorine
Whation is more
is the total electronegative
number of differentthan iodine.
chloroethanes (formula C2 H6-nCln, where n can be any
integer from 1 to 6)?
B neutron
C 8 is much less than that for the H2/I2 reaction.
The activation energy for the H2/Cl2 reaction
A proton
C 6 bondB energy
The 8 of HC 9
I is smaller D the
than 10 bond energy of HCl.
23 D
2-Bromopropane, (CH3 )2CHBr, may be used as the starting point for making (CH3 )2CHCO2H.

D The bond energy of I2 is smaller than the bond energy of Cl2. [S‘02 Q21]
Which of the following sequences would be most suitable?
222 Polymerisation
2 As of chloroethene
a simplification, an adult humangives pvc.
can be considered to have a daily diet of 1.80 kg of
carbohydrate
A the(CH (empirical formula
→ (CH3 )2CHOH CH O).
→ (CH
18 In 3 )2CHBrelectrolysis )2CHCO2H chlorine, the diaphragm used is a porous
industrial of 2
brine to manufacture
How does the carbon-carbon bond in pvc 3compare with that in chloroethene?
screen which allows the flow of electrolytes but keeps other chemicals separate.
B (CH
Which mass
3 )2CHBr → (CHdioxide
of carbon 3 )2CHCN → (CH
does a person
3 )2CHCOproduce
2H each day if all the carbohydrate eaten is
A longer
digested stronger
and oxidised?
Which substance needs to be kept separate from 8 the →chlorine by the Hdiaphragm?
C (CH 3 )2CHBr → (CH3 )2CHOH → (CH3 )2CHCN (CH3 )2CHCO 2
B longer weaker
A
D 0.267 )kg →B(CH 0.800 kg → (CH C ) CHOH
1.32 kg (CH D 2.64 Hkg
21 A (CH3 is
Camphor
hydrogen2CHBr
used for 3 )2CHCN
medical purposes, the 3 2diagram→ shows3 )its
2CHCO
structure.
2

C shorter stronger [S‘02 Q2]

B sodium hydroxide
3 D
324 The
Which
shorter showsweaker
diagram
substance in the mass exhaust
a vehicle spectrumresults
of a sample
from of naturally-occurring
CH3 incomplete combustion copper.
of a hydrocarbon fuel?
C sodium chloride
A
D CO
water B H2O CN2 DC NO
CH2 7 C O

6CH C CH [S‘02 Q24]

3 3
25 Which compound on reaction with CH 5
hydrogen cyanide CH2in aa compound
produces withamount
a chiral than
centre?
19
4 Which gas is present in the exhaust
relative 2fumes of a car engine much greater any
other gas? abundance 4 C
A CH3 CHO 3
A carbon dioxide 2 H
B CH3 CH2COCH2CH3 1
B
How carbon
many monoxide
chiral centres are present in one molecule of camphor?
C CH3 CO2CH3
C nitrogen 61 62 63 64 65 66 67 68
D
A 0 HCHO B 1 C 2 D 9701/1/M/J/02
3 [Turn over
m/e
D water vapour

26 What is the relative

An organic compoundatomic
willmass of this copper?
decolorise dilute acidified aqueous potassium manganate([W‘02 VII) Q19]
on
20
22 warming,
The but
Russian will not
composer decolorise
Borodin bromine
was also water.
a research chemist who discovered a reaction
5 Chloroethane is used as a starting material for the production of ‘time-release capsules’ in in which
A
two 63.3 molecules
ethanal
pharmaceutical B combine
products.63.5
One wayto form aCcompound
of preparing D is
63.6chloroethane
commonly 64.0
known as aldol
to react (reaction
chlorine I). Aldol
and ethane in
What
forms could the
another organic
compound compound
on heating
the presence of ultraviolet light. be?
(reaction II ).

A butane
Which I 2CH3CHO
statement → CH
is correct 3CH(OH)CH
about CHO of the mechanism of this reaction?
the first2stage
B ethanolII –
CH → CH3CH=CHCHO + H2O
A The Cl Cl3CH(OH)CH
bond is split2CHO
homolytically.
C ethene
B The
Which of Cl
the–following
Cl bond best
is split heterolytically.
describes reactions I and II?
D ethanoic acid
C The C – H bond is split homolytically.
I II
D The C – H bond is split heterolytically.
27 A addition X has all elimination
A compound of the following properties:

[W‘02 Q22]
B addition reduction
it is aCH
23 Chloroethene, liquid
= at room temperature 9701/1/M/J/02
and atmospheric pressure;
2 CHCl, is the monomer of pvc.
C elimination reduction
it does not mix completely with water;
Whatsubstitution
D are the C–C–C bond angles along the polymeric chain in pvc?
elimination
it does not decolorise acidified potassium manganate(VII).
A They are all 109 °.
What could X be? [Turn over
B Half are 109 ° and half are 120 °. 9701/1/O/N/02

A
C ethane
They are all 120 °.
B
D ethanoic
They acid
are all 180 °.
C ethanol
CEDAR
D COLLEGE
ethyl ethanoate 122 ALKANES WS 3
 C 30 cm
B magnesium
3
oxide and nitrogen
DD 4040
cmcm
3
C magnesium oxide, nitrogen and oxygen
D Onemagnesium oxide, nitrogenchemical
dioxide and oxygen
262 One ofofthe
themost
most important
important species
chemical species
35Cl •.
responsible for
responsible for the
the removal
removal of
of ozone
ozone from
from the
the
stratosphere is a free radical of chlorine,
stratosphere is a free radical of chlorine, Cl . 35 •

16 Chlorine
What doescompounds show oxidation states ranging from –1 to +7.
35Cl • contain?
What does 35Cl • contain?

What are the reagent(s) and conditions necessary for the oxidation of elemental chlorine into a
compound containing
protons chlorine inelectrons
neutrons the +5 oxidation state?
protons neutrons electrons
AAA AgNO 17
173 (aq) followed
18
18 by NH3 (aq)
16
16 at room temperature
BBB concentrated
17
17 18 at room temperature
SO
H218 4
17
17
CCC cold18 18 NaOH(aq)
dilute 17
17 17
17
DDD hot concentrated
18
18 17
17NaOH(aq) 18
18

8 [W‘02 Q2]

17
23 Which
73 The gaseous
Usecomplete
of the Data hydride
Bookletmost
combustion is of readily
alkanes
relevant todecomposes
question.into
to produce
this its elements
carbon on contact
dioxide and with
water is ana important
hot glass
3 exothermic
rod?
Use of the Data Booklet is relevant to this question.
reaction.
In theline
Which gasonphase, aluminium
the graph shows theandrelationship
a transition between
element require the same
the number amount
of carbon of energy
atoms to form
in the alkane
A
Inoneammonia
the gas phase,
mole of an aluminium
ion with a 2+and a transition element require the same amount of energy to form
charge.
and the number of moles of oxygen gas needed for complete combustion of the alkane?
one mole of an ion with a 2+ charge.
B hydrogen chloride
What is the transition element?
Whathydrogen
C is the transition
iodide element? A
A Co B
D
A steam
Co
B Cr
B Cr
C Cu
18 Which reagent, when number
mixed and of heated with ammonium sulphate, C liberates ammonia?
C Cu
D Ni moles of
A
D aqueous
Ni bromineoxygen gas 8
B dilute bromide
21 Hydrogen hydrochloric acid
reacts with ethene to form bromoethane. D
C limewater
What is the best description of the1organic intermediate in this reaction?
D acidified potassium dichromate(VI) number of carbon atoms in alkane

A It contains carbon, hydrogen and bromine. 9701/1/O/N/02 [S‘03 Q23]

9701/1/O/N/02
19
24 B It has
Which a negative
pollutant
8 Cyclohexa-1,4–diene charge.
is formed
is in thewith
treated internal combustion
a solution engine
of bromine and, if not removed by the catalytic
in tetrachloromethane.
converter, may become involved in the formation of acid rain?
C It is an electrophile.
A
D It B radical.
C is a free C8 H18 C CO D NO

[S‘03 Q19]

20
22 Howstrong
9 On many structural
heating aand cis-trans isomers
hydrocarbon areethene,
produces there forpropane
dichloropropene, C3 H4 Clin2 ? the mole ratio
and but-1-ene
5 : 1 : 1. cyclohexa-1,4-diene
A 3 B 5 C 6 D 7
What is the molecular
Which product is formed? formula of the hydrocarbon?

A C17H34 A B C17H36 C C19H38 D C19H40 B

[W‘03 Q22]
Br 9701/1/M/J/03

23 1,2-Dibromo-3-chloropropane (DBCP) has been used in the control of earthworms in agricultural

land. Br Br Br

What would be the best synthesis of this compound?

A 2 → DBCP + 2HBr
CH3CH2CH2Cl + 2BrBr Br Br
B CH3CHBrCH2Br + Cl2 → DBCP + HCl
Br
C CH2=CHCH2Cl + Br2 → DBCP
D C 2 + PBr5 → DBCP + PBr3
ClCH2CH=CH D
CEDAR COLLEGE Br 123 ALKANES WS 3
Br Br
24 Each of the following compounds is effective as a refrigerant.
 A 6.55 % B 13.1 % C 26.2 % D 30.0 %

3
10 A sample of the hydrocarbon C6H12 is completely burned in dry oxygen and the product gases are
collected as shown.
[Ar : H, 1 ; C, 12 ; O, 16.]

H2O + CO2 + excess of O2 excess of O2

P Q

sodalime
anhydrous calcium (to absorb CO2)
chloride
(to absorb H2O)

The increases in mass of the collecting vessels P and Q of the apparatus are MP and MQ,
respectively.

What is the ratio MP / MQ?

A 0.41 B 0.82 C 1.2 D 2.4

8 [W‘03 Q3]

11 Which compound could not be obtained from cracking a sample of nonane, CH3 (CH2)7 CH3 ?
23
9701/1/O/N/03
A CH3 CH=CHCH=CHCH2CH2CH2CH3
B CH3 CH2CH2CH2CH3
C CH3 CH2CH2CH2CH2CH=CH2
D (CH3 CH2CH2)3 CH
[S‘04 Q23]

24 In which way are ethene and propane similar?

CH2=CH2 CH3 CH2CH3

ethene propane

A They are both obtained by the dehydration of alcohols.

B They are both neutral to an indicator solution.
C They can both be hydrogenated using a suitable catalyst.
D They can both undergo polymerisation under suitable conditions.

25 Which reaction in the catalytic converter does not remove hazardous and polluting gases from
the exhaust fumes of a motor car?

gases going out

CEDAR COLLEGE 124 ALKANES WS 3
 D They can both undergo polymerisation under suitable conditions.
2

12
25 Which reaction in the catalytic converterSection
does not
A remove hazardous and polluting gases from
the exhaust fumes of a motor car?
For each question there are four possible answers, A, B, C, and D. Choose the one you consider to
be correct.
gases going out
1 Granular urea, CON2 H4 , can be used to remove NO2 from the flue gases of power stations,
converting it into harmless nitrogen.

gases going in: 2CON2 H4 + x NO2 → 2CO2 + y H2 O + z N2

carbon monoxide,
Whathydrocarbons
are the values of x, y and z in a balanced equation?
surfaces coated
and oxides of
with platinum and
xnitrogen y z rhodium catalyst
A 1½ 2 1¼
These equations are qualitative and unbalanced.
B = unburnt
[HC 2 4 3 NOx = oxides of nitrogen]
hydrocarbons;

AC HC +3NOx ! H
4 O + CO
2
3½+ N
2 2
D 3 4 3
B CO + NOx ! CO2 + N2 Section A
C HC + NOx ! H2O + CO2 + N2
2For The
eachdiagram
questionshows
there the
are mass
four possible
spectrumanswers, A, B, of
of a sample C,zinc.
and D. Choose
Use thetoone
the data you consider
calculate to
the relative
be correct.
D CO
atomic + O2of!the
mass CO 2
sample.

[S‘04 Q25]
100
13
1 Granular urea, CON2 H4 , can be used to remove NO2 from the flue gases of power stations,
converting it into harmless nitrogen.
80
2CON2 H4 + x NO2 → 2CO2 + y H2 O + z N2
relative 60
What are the values ofabundance
x, y and z /in%a balanced equation?
40
! UCLES 2004 x y z 9701/01/M/J/04
20
A 1½ 2 1¼
B 2 4 3 0
64 65 66 67
C 3 4 3½ Ar

A D 65 3 4B 3
65.25 C 65.5 D 65.66

[W‘04 Q1]

314
2 The
The foul
diagram
smellshows the mass
that skunks spectrum
spray of to
is due a sample of zinc.
a number Use the
of thiols, onedata to calculate
of which the relative
is methanethiol,
atomic mass of the sample.
CH3SH, which burns as follows.

CH3SH +100
3O2 → CO2 + SO2 + 2H2 O

80exploded with 60 cm3 of oxygen.

A sample of 10 cm3 of methanethiol was

volume of the 60
What would be the finalrelative resultant mixture of gases when cooled to room
temperature? abundance / %
40C
A 20 cm3 B 30 cm3 50 cm3 D 70 cm3

[W‘04 Q3]
20
© UCLES 2004 9701/01/O/N/04
0
64 65 66 67
Ar

CEDAR
A COLLEGE
65 B 65.25 C 125
65.5 D 65.66 ALKANES WS 3
 X)
x 8.31 x (273 + 273
1.6 x 10 H C C Y
D step−I3 step
HPaIIC C step III
3.0 x 10
CH3CH2OH CH3CHO C H
H CCH CH(OH)CH CHO CH2=CHCH=CH2
H C 3C H 2
H C H buta-1,3-diene
H C H
15
9 Which of these compounds, on complete combustion H of one mole, will release the greatest
Which
amountterm H I? CC H
could be used to describe step
of energy?
H C H
A condensation
CH3CH2CH2OH C H
H
B dehydration
CH3CH2CH3 H
What
C is a true statement
dehydrogenation
CH about the functional groups X or Y?
What is3CH 2CO
a true 2H
statement about the functional groups X or Y?
A X will undergo nucleophilic addition.

D
A hydrogenation
CH 3COCH
X will 3
undergo nucleophilic addition.
B Y will
will undergo
undergo nucleophilic
nucleophilicaddition.
addition. [W‘04 Q9]
B Y
16
23
10 How Xmany
At high
C different electrophilic
temperatures,
will undergo substitution products
steam decomposes are its
into
substitution. possible,
elements in principle,
according when
to the afollowing
mixture equation.
of bromine
C ethane
and X will undergo electrophilic
is allowed to react? substitution.
D
D 3Y Y will
will undergo electrophilic2H
undergo electrophilic 2O(g)
substitution.
substitution.
2H2(g) + O2(g)
A B 5 C 7 D 9

In one experiment at 1 atm pressure, it was found that 20 % of the steam had been converted [W‘04 into
Q23]
hydrogen and oxygen.
17
25
25 Which reaction occurs
Which reaction occurs with
withsaturated
saturatedhydrocarbons?
hydrocarbons?
What are the values of the equilibrium partial pressures, in atm, of the components of this
A
A catalytic hydrogenation
catalytic hydrogenation
equilibrium?
B ready decolourisation
decolourisationof ofaqueous
aqueousbromine
bromine
partial pressure partial pressure partial pressure
C polymerisation
polymerisation
of steam of hydrogen of oxygen
D thermal
thermal0.80
cracking
cracking
A
x 1 0.10 x 1 0.10 x 1

1.0 1.0 1.0 [W‘04 Q25]

0.80 x 1 0.133 x 1 0.067 x 1
18
26 B reaction
26 The reaction of chlorine
chlorinewith
of1.0 withmethane
1.0 isiscarried
methane carriedout
outinin
the
1.0thepresence
presenceofof
light.
light.
© UCLES 2004is 0.80 x 1 0.20 x 9701/01/O/N/04
1 0.10 x 1
What
C is the function
What 1.0 of
function of the
thelight?
light? 1.0 1.0
A to break
break0.80
the
the C Cx–
–H1
H bonds 0.20
bondsinin x 1
methane
methane 0.10 x 1
D 1.1 1.1 2 1.1
B to to break
break up
up the
the chlorine
chlorinemolecules
moleculesinto
intoatoms
atoms
Section A
CC toto break
break up
up the
the chlorine
chlorinemolecules
moleculesinto
intoions
ions
For each question there are four possible answers, A, B, C, and D. Choose the one you consider to
D toto heat
heat up
up the
the mixture

D
be correct. mixture
[W‘04 Q26]
© UCLES 2004 9701/01/O/N/04
19
1 A pure hydrocarbon is used in bottled gas for cooking and heating.

When 10 cm3 of the hydrocarbon is burned in 70 cm3 of oxygen (an excess), the final gaseous
mixture contains 30 cm3 of carbon dioxide and220 cm3 of unreacted oxygen. All gaseous volumes
were measured under identical conditions.
Section A
What is the formula of the hydrocarbon?
For each question there are four possible answers, A, B, C, and D. Choose the one you consider to

A C 2H 6
be correct. B C3H6 C C3H8 D C4H10
[S‘05 Q1]
[Turn
it isover
20
© UCLES 2004 9701/01/O/N/04
1© The
2 UCLES petrol additive
On collision,
2004 airbagstetraethyl-lead(IV), Pb(C
in cars inflate rapidly due2Hto5)the
4, isproduction
now banned
9701/01/O/N/04 in many countries. When
of nitrogen. [Turn over
completely burned in air, lead(II) oxide, CO2 and H2O are formed.
The nitrogen is formed according to the following equations.
How many moles of oxygen are required to burn one mole of Pb(C2H5)4?
2NaN3 → 2Na + 3N2
A 9.5 B 11 C 13.5 D 27

10Na + 2KNO3 → K2O + 5Na2O + N2 [W‘05 Q1]

2 Which ion has

How many more
moles electronsgas
of nitrogen than protons
are andfrom
produced more1 protons than neutrons?
mol of sodium azide, NaN3?

A 1.5 B 1.6 [H = 11 H C
; D =3.212 H ; O = 16
8 O]
D 4.0

CEDAR
A COLLEGE
D– B H3O+ C 126
OD– D OH– ALKANES WS 3
3 The first six ionisation energies of four elements, A to D, are given.

Which element is most likely to be in Group IV of the Periodic Table?

 19 Two properties of non-metallic elements and their atoms are as follows.
D ethanol + phosphorus pentachloride
property 1 has an oxide that can form a strong acid in water

21 property
24 Light initiates 2 has no
the following paired 3p electrons
reaction.
Which properties doalkane
phosphorus and →
+ chlorine sulfur have?
chloroalkane + hydrogen chloride

phosphorus
What happens sulfur
to chlorine in this photochemical reaction?

A A heterolytic
1 and 2 to give an electrophile
fission 1 only

B B homolytic1 fission
only to give an electrophile
1 and 2

C C heterolytic
1 and 2 to give a free
fission 1 and 2
radical
D D homolytic2 fission
only to give a free
1 only

radical
[S‘06 Q24]

22
20 High-energy
25 When gaseous chemicals
irradiation arestratosphere
in the transported by road or radicals
produces by rail they are
from classified as follows.
chlorofluoroalkanes, commonly
known as CFCs.
flammable non-flammable poisonous
Which radical could result from this irradiation of CHFClCF2Cl?
Which commonly transported gas is non-flammable?
A CHFClCFCl
A butane
B
B CHClCF 2Cl
hydrogen
C
C CHFCF
oxygen2Cl

D
D CFClCF
propene2Cl

[W‘06 Q24]

© UCLES 2006 9701/01/M/J/06

© UCLES 2010 9701/11/M/J/10

CEDAR COLLEGE 127 ALKANES WS 3

 4

23
4 Samples of 10 cm3 of each of the first four members of the alkane series are separately mixed
with 70 cm3 of oxygen. Each is then burned and7 the total volume, V, of residual gas measured
again at room temperature and pressure.
19 Which molecules, each with a linear carbon chain, can have an optically active isomer?
Which graph represents the results that would be obtained?

A B
I II III IV

V / cm3 C3 H6 BrI C3 H4 BrI V 3/ H

C cm6 I32 C3 H4 Br2
X
A I and80II only 80
X
B I, II and
60 III only 60
C II and III only X
40 X 40
D I, II and IV only X X
20 X 20
X
0 0
20 In which pair do the isomers have identical boiling points?
CH4 C3 H 8 CH4 C3 H8
A CH CH CH CH OH andC4H(CH
3
C
2
2 H 6
2
10
2 ) CHCH OH 3 2 2
C 2H 6 C4H10

B C D
CH3 (CH2 )4 CH3 and (CH3 )2 CHCH(CH3 )2
V / cm 3
V / cm 3

80 CH3 CH3 80

C H 60 C and C H 60 X
X
X X
Cl 40 CH2 Cl X Cl H 2 C Cl 40
X
X
20 X 20
CH3 H CH3 CH3
D 0 C C and C C 0
CH4 C3 H 8 CH4 C3 H8
H CH
C 2H36 C4H10 H H C 2H 6 C4H10

[W‘06 Q4]

24
21 Tetramethyl-lead(IV), (CH3 )4 Pb, increases the rate of the reaction of methane with chlorine.

CH4 (g) + Cl2 (g) → CH3 Cl(g) + HCl(g)

Why can tetramethyl-lead(IV) behave in this way?

A It is a source of methyl radicals.

B It releases CH3+ (g) .

C It reacts with chloromethane and prevents equilibrium being established.

D Metal ions catalyse the reaction.
[W‘07 Q21]

© UCLES 2006 9701/01/O/N/06

CEDAR COLLEGE 128 ALKANES WS 3

© UCLES 2007 9701/01/O/N/07 [Turn over

 2

8
22 Chloroethene, CH2=CHCl, is the monomer of PVC.
7
25
22 What
Whicharereaction occurs when ethane and
thechlorine arechain
mixedin in diffused sunlight?
20 Sorbitol isthe C−C−C bond angles
a naturally-occurring along
compound polymeric
with a sweet taste. PVC?
It is often used as a substitute for
sucrose by the foodsubstitution
A a free-radical industry. with hydrogen given off
A They are all 109.5°.
The
B diagram
B Half showssubstitution
a free-radical
are 109.5° its structure.
and half arewith hydrogen chloride given off
120°.

C a free-radical
They are all 120°. H
substitution with no gas given off

D a nucleophilic
They H C chloride
substitution with hydrogen
are all 180°. O H given off
H C O H [W‘07 Q22]

26
23 Which
23 hydrocarbon
Limonene wouldin not
is an oil formed beH of
the peel Ocitrus
C fruits.
collected Hin the inverted tube by heating pentane,
CH3(CH2)3CH3, in the apparatus shown?
HCHC OCHH
3 2
pentane on aluminium C
mineral fibre oxide
H C O H
H C Ohydrocarbons
H
H

How many chiral centres are present in sorbitol?

CH3
limonene
A 1 B 2 C 3 D 4

Which very strong

product is formed
21 The compound heat
‘leaf alcohol’when molecular
is partly bromine
responsible for thereacts
smell with limonenegrass.
of new-mown at room temperature in
the dark?
CH3CH2CH=CHCH2CH2OH
A B C D
leaf alcohol
Br Br
CH3 CH2 CH3 CH2
Which twoCcompounds will be formed
C water
when ‘leafCH C isCH
alcohol’
3 2Br
oxidised CH3 hot,
using CH2Br
C concentrated
manganate(VII) ions?
Br
A
A CHCH34CO2H and HOCH2CH2CH2CO2H
B CH33CO
CH CH23H and HO2CCH2CH2CO2H Br
B Br
C CH3CH
CH CH
2CO
CH Br
2H and HO2CCH32CO2H CH3 CH3 Br
C CH3 2 3
CH=CH 2

D
D CH
CH33CH
(CH2CO 2H3and HOCH2CH2CO2H
2)8CH

[S‘08 Q23]
24 The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below.
27
22 Which hydrocarbon can form a monochloro-substitution derivative which shows both chirality
and cis-trans isomerism? HF Br2
CCl2=CHCl CF3CH2Cl CF3CHBrCl
© UCLES 2008
A CH3CH=CH2 stage 19701/01/M/J/08 stage 2 [Turn over

B
Which 3)2C=CH
(CHtype of reaction
2 is occurring in stage 2?
C CH3CH=C(CH3)2
A electrophilic addition

D CH3CH=CHCH2CH3
B electrophilic substitution
[W‘08 Q22]
C free radical substitution
D nucleophilic addition

© UCLES 2008 9701/01/O/N/08 [Turn over

© UCLES 2007 9701/01/O/N/07

CEDAR COLLEGE 129 ALKANES WS 3

 2 3

24 Sorbic acid is used as a food preservative because it kills fungi and moulds.
A 10.0 tonnes B 12.7 tonnes C 14.0 tonnes D 17.7 tonnes
H H O
28 C
2
C
2 Carbon disulphide vapour burns in oxygen according
C
to the following equation.
HC C C OH
CS23(g) + 3O2Section
(g) → COA2(g) + 2SO2(g)

For each question

A sample of 10 cm3 are
there four possible
of carbon answers,
disulphide A,HB, C,inand
Hwas burned D. 3Choose
50 cm the one
of oxygen. Afteryou considerthe
measuring to
be correct.
volume of gas remaining, the product was sorbic acidwith an excess of aqueous sodium hydroxide
treated
and the volume of gas measured again. All measurements were made at the same temperature
and pressure,
Sorbic acid willunder
react such
with conditions that carbon disulphide was gaseous.
1 An element X consists of four isotopes. The mass spectrum of X is shown in the diagram.
What were the measured volumes?
100
• hydrogen in the presence of a nickel catalyst,
• bromine volumein anof organic
gas solvent. volume of gas after
80
after burning / cm 3
adding NaOH(aq)
2 / cm3
How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by
these
A reactions? 30 60
relative Section 0A
B abundance30 20
For each question of%hydrogen
moles there 40 possible
are four molesanswers,
of bromineA, B, C, and D. Choose the one you consider to
be correct.
C 50 20
50 20
A 2 2
D 40
B 2 2 21

1 Use of the Data Booklet is relevant to this question.

0 [W‘08 Q2]
90one electron91 only inofan92 in93 94states?
C 3 2
29
3 In which
leadedpair do both
petrol thereatomsis anhaveadditive composed
1
s orbital
lead, carbon their
andground
hydrogen only. This
D 3
compound contains 29.7 % carbon and 6.19 % hydrogen2 2 mby / e mass.
A Ca, Sc B Cu, Be C H, He D Li, Cr
What is the value
relativeof atomic
x in themass of X?formula PbC8HX?
empirical
25 Bromine reacts with ethene to form 1,2-dibromoethane.
4 A Use 5 of the Data Booklet B 6 is relevant to this Cquestion.
C 16 D
D 20
91.00 91.30 91.75 92.00

What is the correct description of the organic intermediate in this reaction? [S‘09 Q1]
Hard water contains calcium ions and hydrogencarbonate ions arising from dissolved calcium
30 0.200
2 hydrogencarbonate,
A household
It has a bleach
mol aofnegative Ca(HCO
contains
charge.
hydrocarbon 3)2. sodium
undergo chlorate(I),
complete NaClO,
combustion as 35.2
to give its gactive ingredient.
of carbon dioxide The
and
concentration of NaClO in
14.4 g of water as the only products. the bleach can be determined by reacting a known amount with
B
HowItmany
aqueous is ahydrogen
free radical.
electrons are present
peroxide, H2O2in. the hydrogencarbonate anion?
WhatIt is
C the molecular formula of the hydrocarbon?
A 30is a nucleophile. B 31
NaClO(aq) + H2O2(aq) C →32 NaCl(aq) + O2(g) D + 33H2O(l)
A C H
D It 2is an4 B
electrophile. 2 6C H C C H
4 4 D C 4H 8
When 25.0 cm3 of bleach is treated with an excess of aqueous H2O2, 0.0350 mol of oxygen gas is
[W‘09 11 Q2]
given off.
31
26 Which equation represents a valid propagation step in the free radical reaction between ethane
Whatchlorine?
and is the concentration of NaClO in the bleach?
–4 –3
A 8.75 Cl • mol
C2H6 ×+10 → Cdm
2H5Cl + H
•
© UCLES 2008 9701/01/O/N/08
B 0.700
C2H5Clmol dm•–3→ C2H4Cl • + HCl
+ Cl
–3
C
C C2H6 +mol
0.875 H• dm
→ C2H •5 + HCl
D 1.40 mol dm–3
D C2H5• + Cl • → C2H5Cl
[W‘09 12 Q25]
3 The first seven ionisation energies of an element between lithium and neon in the Periodic Table
are as follows.

1310 3390 5320 7450 11 000 13 300 71 000 kJ mol–1

© UCLES
What2009
is the outer electronic configuration9701/11/O/N/09
of the element? [Turn over

A 2s2 B 2s22p1 C 2s22p4 D 2s22p6

© UCLES 2009 9701/11/O/N/09

CEDAR COLLEGE 130 ALKANES WS 3

 Sorbic acid will react with
9
• hydrogen in the presence of a nickel catalyst,
32
21 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution.
• bromine in an organic solvent.

In a propagation
How many molesstep the free radical
of hydrogen X• is formed.
and of bromine will be incorporated into one mole of sorbic acid by
these reactions?
CH3
moles of hydrogen moles of bromine ●
CH3CH2 C CH3 + Cl → X● + HCl
A 2 2
CH3 1
B 2 22
•
How
C many different
3 forms of X are possible?
2
1
AD 1 3 2 2C

B 2 3 D 4
[S‘10 11 Q21]
10
33
22 When
22 What heated
will react
with differently withhydrocarbon
chlorine, the the two 2,2-dimethylbutane (CH3)3CCH
isomeric alcohols,undergoes 2OHradical
free and
(CH3)2CHCH2CH2OH?
substitution.
29 The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic rubber.
A a propagation
acidified aqueous
step apotassium
free radicalmanganate(VII)
H CH3
In X• is formed.

CH3
B concentrated sulfuric acid
C C
C phosphorus pentachloride
CH3CH2 C HCH3 + Cl •CH→3 X• + HCl
D sodium 9
CH3are x other isomers of C H , structural or otherwise, which
21 In addition toacid
Butanedioic 2-methylpropene
occurs in amber,there 4 8
algae, lichens, sugar cane and beets. It may be synthesised in
contain a
two steps double bond.
from will
1,2-dibromoethane.
23 Which reagent give similar results with both butanone and butanal?

step 1 step 2
Whatmany
How is thedifferent
value of forms
x? of X• are possible?
A acidified aqueous potassium dichromate(VI)
BrCH2CH2Br X HO2CCH2CH2CO2H
A
B 1an alkaline solution
B containing
2 C 3 Cu2+ ions (Fehling’s
complexed D 4 solution)

[S‘10 11 Q21]
Which +
C anreagents
aqueous could be containing
solution used for this synthesis?
[Ag(NH 3)2] (Tollens’ reagent)
34
30 Which environmental problem is not made worse by the release of oxides of nitrogen from car
D 2,4-dinitrophenylhydrazine
engines? step 1 reagent
step 2

A A acidification
HCN(g)
of lakes HCl (aq)
24 What is formed when propanone is refluxed with a solution of NaBH4?
B B corrosion
HCO of2Na(aq)
buildings HCl (aq)
A propanal
C C photochemical
KCN(aq / alcoholic)
smog H2SO4(aq)
B propan-1-ol
D D the holeNaOH(aq)
in the ozone layerK2Cr2O7 / H2SO4(aq)

C propan-2-ol [W‘10 11 Q30]

© UCLES 2013 9701/12/M/J/13
35
22 D The propane
formula CH3 can represent an anion, a cation or a free radical. Species with the molecular
formula CH3 can act as an electrophile, a free radical or a nucleophile depending on the number
of outer shell electrons on the central carbon atom.
25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium
hydroxide?
How many outer shell electrons must be present for CH3 to act in these different ways?

CH3OH B C3H7OH C3H7CO 2− Na +

CH3 as3a 7 2
A C C H CO H D
CH3 as an CH3 as a
electrophile free radical nucleophile

A 6 7 8
B 6 8 7
C 7 6 8
© UCLES 2010 9701/11/M/J/10 [Turn over
D 8 7 6

[S‘11 11 Q22]

23 Pentanol, C5H11OH, has four structural isomers that are primary alcohols.
CEDAR COLLEGE 131 ALKANES WS 3
How many of these primary alcohols contain a chiral carbon atom?

A 0 B 1 C 2 D 3
 8
10

36
23 The
23 Isomers X andobtained
products Y both react with HBr.
by cracking an alkane, X, are methane, ethene and propene.
Br
H3C in the products
The mole fraction of ethene is 0.5. Br Br

C C C C
What is the identity of X?
HC Br H 3C CH
A C6H14 B 3C8H18 C C9H20 D C11H324

X 7 Y [S‘11 12 Q23]

37
19 Which
24 Carboncompound
A mixture
monoxide,doesCO, nitrogen
of X and Y is not showmonoxide,
reacted cis-trans
with
NO, and sulfur dioxide, SO2, may all be present in the
HBr. isomerism?
exhaust fumes from a car engine.
A 2-methylpent-2-ene 8
Which three structures represent three different possible products of this reaction?
Which reaction concerning these compounds occurs in the atmosphere?
21 B 3-methylpent-2-ene
An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers.
A
A CO(CHis 3)2spontaneously
CHCBr3 (CH3)2CBrCHBr
oxidised to CO2 2 CH3CHBrCHBrCH3
C 3,4-dimethylhex-3-ene
What
B is R3)?2CHCBr3
(CH (CH3)2CBrCHBr2 CH3CBr2CHBrCH3
B NO 2 is reduced to NO by CO
D pent-2-ene
A
C H
C (CH23is
NO reduced3 B
)2CBrCBr Cl(CH
to NO 3)2CHCBr
by SO 3C D C2H35
CH3 CH3CBr2CHBrCH
2

D
D SO )2CBrCHBr
(CH2 3is oxidised 2 SO3CHBr
to by CO 2CBr(CH 3)CH3
2and propanal
CH3CHBrCBr2CH3
25 Which formulae show propanone as different compounds?
22 Menthol is an important compound extracted from the peppermint plant. [S‘12 11 Q19]
A empirical, molecular, structural and displayed formulae
38
24
20 Oct-1-ene,
Fumaric acid (CH2be
CH3can )5CH=CH 2, is subjected
converted CH
to thermal
3
into oxaloacetic acidcracking.
by a two-step process involving the
B molecular,
intermediate Q. structural and displayed formulae only
Which combination of compounds W, X, Y and Z can be obtained?
C structural and displayed formulae steponly
1 step 2
HO2=CH
2
CCH=CHCO H Q HO3 2CCOCH
CH22CO H
only 2 2
CH CH CH=CH CH3CH2CH =CHCH=CH
OH
2 3 2 2
D displayed formulae
Wfumaric acid X Y oxaloacetic acidZ

26 EachW,
How
A of X,
manythese steps
Yisomers
and can be
Z with theachieved in5H
formula C H 3Chave
the CH3 by a single reagent.
10 laboratory
structures that involve π bonding?

What
A
B could
3W, be Y
X and the intermediate
onlyB 4 Q and theCmenthol
reagent
5 for step 2? D 6

C W,
How X and
many Z only
chiral centres are there in one molecule of menthol?
Q reagent for step 2
27 1,1-dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal.

D 1W and X only B 2
A C 3 warm acidified D 4
A HO2CCHBrCH2CO2H KMnO 4
NaOH(aq) [S‘12 12 Q24]
B CH3 CH2 CHCl
HO2CCHBrCH(OH)CO 2H 2 CH3 CH2 CHO
warm NaOH(aq)
39
23 The cracking of a single hydrocarbon molecule, CnH2n+2, produces two hydrocarbon molecules
C Each hydrocarbon
only. HO2CCH(OH)CH 2CO2
product H
contains the sameFehling’s
numbersolution
of carbon atoms in one molecule.
Which
Each term describes
hydrocarbon the
product first
has step of this
non-cyclic reaction?
structural isomers.
D HO CCH(OH)CH CO H
2 2 2 warm acidified K Cr O 2 2 7
A electrophilic addition
What is the value of n?
21 B
A
elimination
An organic
4 compoundB J6 reacts with sodium
C 8 to produce anD organic
9 ion with a charge of –3.
J reacts with NaOH(aq) to produce an organic9ion with a charge of –1.
C nucleophilic substitution [W‘12 11 Q23]

40
24 What
25 D could
the be
Oneoxidation
of the is
structural
reactions
But-2-ene-1,4-diol taking formula
converted place inofsteps
in two aJ?catalytic
throughconverter in a carXexhaust
an intermediate system is between
into ketobutanedioic acid.
nitrogen oxide and octane (unburned petrol). The products of this reaction are non-toxic.
hot acidified KMnO4
A HO2CCH(OH)CH2CO2H

HOCH CH=CHCH OH X HO2CCOCH2CO2H

Which
B HO is the correct equation for the reaction?
2CCH(OH)CH 2CHO
2 2
step 1 step 2
C C8Hbut-2-ene-1,4-diol
A HOCH 16 + 16NO → 8CO + 8N2 + 8H2O
2CH(OH)CH2CO2H ketobutanedioic acid
B HOCH
D C8H16 + 24NO2CHO
2COCH → 8CO2 + 12N2 + 8H2O
What could be the reagent for step 1 and the intermediate X?
C C8H18 + 17NO → 8CO + 8 21 N2 + 9H2O
reagent for step 1 X
D C8H18 + 25NO → 8CO2 + 12 21 N2 + 9H2O
A cold acidified KMnO4 HOCH2CH2CH(OH)CH2OH [W‘12 11 Q25]
© UCLES
© UCLES 2011
2012 9701/12/M/J/12
9701/12/M/J/11
B hot acidified KMnO OHCCH(OH)CH2CHO
26 High-energy radiation in the 4stratosphere produces free-radicals from chlorofluoroalkanes,
commonly
C known
steam and as CFCs.
concentrated H2SO4 HOCH2CH(OH)CH2CH2OH
CEDAR COLLEGE 132 ALKANES WS 3
D
Which warm acidified
free-radical is most Klikely
2Cr2O HO
to7 result from the 2CCH=CHCO
irradiation 2H
of CHFCl CF2Cl ?
 correct.
C ethanolic
hydrogen sodium
cyanidehydroxide, followed by bromine
D ethanolic
potassiumsodium hydroxide, followed by hydrogen bromide
cyanide
41 A mixture of 10 cm3 of methane and 10 cm3 of ethane was sparked with an excess of oxygen.
1
After cooling to room temperature, the residual gas was passed through aqueous potassium
hydroxide.sodium hydroxide reacts with 1-bromopropane to give propan-1-ol.
25
24 A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an
Aqueous
organic ion in which a carbon atom has a positive charge.
What volume of gas was absorbed by the alkali?
How should the first step in the mechanism be described?
What is involved in the mechanism of the reaction between aqueous sodium hydroxide and
A by a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane
A 15 cm3
2-bromo-2-methylbutane?
–
Cδ+ atom
B 20 cm3
B heterolytic
A by a curly arrow from the
bond fission followed byof
an1-bromopropane to the OHon
attack by an electrophile ion
a carbanion
C
B 30acm
by 3
C heterolytic
curly arrow from the
bond fission C–Br bond
followed by antoattack
the C by
atom
a nucleophile on a carbocation

D
D
C by cm3homolytic
40the
homolytic fissionfollowed
bond fission of the C–Br bond
by an attack by an electrophile on a carbanion

[S‘13 11 Q2]
D homolytic bond fission followed by an attack by a nucleophile on a carbocation
42
2 One of the most important chemical species responsible for the removal of ozone from the
25 Pentane, C5H12, is reacted with chlorine in the presence of ultraviolet light. A compound R is
stratosphere is a free radical of chlorine, 35Cl •. C5H10Cl 2. Each molecule of R contains one chiral
found in the products. R has molecular formula
26 Which
carbon compound
atom. gives an organic product with a lower boiling point when it is heated under
reflux with an excess of acidified potassium dichromate( VI)?
What does 35Cl • contain?
Which two atoms of the pentane chain could be bonded to chlorine atoms in this isomer?
A 2-methylbutan-1-ol 10

A 1 and 3 B 1 and 5 C 2 and 3 D 2 and 4

protons neutrons
B 2-methylbutan-2-ol electrons
26 Use of the Data Booklet is relevant to this question. [S‘13 11 Q25]
CA pentan-1-ol
17 18 16
43 Which volume of oxygen measured at room temperature and pressure is needed for complete
DB pentan-2-ol
combustion17 of 0.1 mol
18of propan-1-ol?
17

AC 10.818
dm3 17 12.0 dm3 17 C 21.6 dm3 24.0 dm3

B D
D of the
27 Use 18Data Booklet
17 is relevant
18to this question. [S‘13 12 Q26]

44
27 Which volume
carbonylofcompound
oxygen, at reacts with hydrogen
room temperature andcyanide to is
pressure, form a product
needed that hascombustion
for complete no chiral
carbon
of atom?
0.1 mol of ethanol?
3© UCLES
Use2013
of the Data Booklet is relevant to this9701/11/M/J/13
question.
A 7.2 dm3
butanone B 8.4 dm3 C 14.4 dm3 D 16.8 dm3
In the gas phase, aluminium and a transition element
4 require the same amount of energy to form

B ethanal [S‘13 13 Q27]

one mole of an ion with a 2+ charge.
45
7 CWhich stage in the free radical substitution of methane by chlorine will have the lowest activation
propanal
What is the transition element?
energy?
D propanone
A CH
A Co3• + Cl 2 → CH3Cl + Cl •

28 B Cl
B
How Cr • + of
many Clthe
• → Cl 2 compounds produce a carboxylic acid on heating under reflux with hot
following
acidified K2Cr2O7?
C Cl
C Cu• + CH4 → CH3• + HCl
D Cl Ni CH 3CH2CHO
D 2 → Cl • + Cl •

CH3COCH3 [W‘13 12 Q7]

8 Use of the 3CH2Booklet

CHData CH2OH is relevant to this question.

The2013 CH3CHOHCH
approximate 3
percentage composition of the atmosphere on four different planets[Turn
is given in
© UCLES 9701/13/M/J/13 over
the table below.
A 1 B 2 C 9701/1/O/N/02
3 D 4
The density of a gas may be defined as the mass of 1 dm3 of the gas measured at s.t.p.
29 Compound
Which mixtureY ofhas of the
Mr has
gases 88.greatest
It does not fizz when added to a solution of sodium
density?
hydrogencarbonate. It can be hydrolysed by dilute sulfuric acid to produce two organic products
with Mr values of 46 and 60.
major gases /
planet
% by number
What is the identity of compound Y? of molecules

A A butanoic
Jupiter
acid H2 89.8, He 10.2

B B ethylNeptune
ethanoate H2 80.0, He 19.0, CH4 1.0

C C 3-hydroxybutanal
Saturn H2 96.3, He 3.25, CH4 0.45
CEDAR COLLEGE 133 ALKANES WS 3
D D butylUranus
methanoate H2 82.5, He 15.2, CH4 2.3
the
For statements
each of thethat you consider
questions in this to be correct).
section, one or more of the three numbered statements 1 to 3 may
2 Ammonia behaves as a base.
be correct.
The responses A to D should be selected on the basis of
3 whether
Decide The oxidation
each of number of the hydrogen
the statements is or is notchanges.
correct (you may find it helpful to put a tick against
the statements that you consider to be correct).
A B SECTION B C D
37
The responses A to
Which compounds
1, D should
2 and are becis-trans
3show selected on the
arebasis
1 and 2 isomerism?
only of 3 only are
2 and 1 only is correct
correct correct correct
1 but-2-eneA B C D
No other combination of statements is used as a correct response.
2 but-1-ene
1, 2 and 3 1 and 2 2 and 3 1 only
are only are only are is
3 2-methylpropene
correct correct correct correct
31 Silicon tetrachloride, SiCl4, is a liquid of low boiling point. In the presence of water it decomposes
to form silicon(IV) oxide and hydrogen chloride.
No other
381 When combination of statements
octane is subjected is used as
to catalytic a correct
cracking, response.
which compounds can be obtained?
What types of bonding occur in SiCl4(I)?
Use of the Data Booklet may be appropriate for some questions.
1 CH2=CH2

A
1 co–ordinate bonding
2 covalent
2 CH3CH2bonding
CH=CH2
31 Which statements about the atoms 23Na and 24Mg are correct?
3
3 CH3der
van (CHWaals
2)4 CHforces
3
1 They have the same number of filled electron orbitals.

[N‘02 Q38]
2 They have the same number of neutrons.13
39
32 Which ions alkanes
2 Long-chain are present in a solution
are converted of ethanol
on an industrialinscale
an excess of concentrated
into alkylsulphates sulphuric
for use acid?
as detergents,
3 They are
e.g. sodium
37 Which both reducing
laurylrepresent
equations agents.
sulphate.stages in the Contact process for manufacturing sulphuric acid?
1 CH3CH2O–
1 S + O2 → +SO2
2 CH O
32 Which 3CH2OH2 contain covalent bonds?
compounds
2 H2O + SO2 → H2SO3
HSO– 1 chloride

A
13 aluminium CH3(CH2)10CH2O S ONa
3 H2SO34 + 2 O2 → H2SO4
2 ammonia O
40 3In the reaction
calcium between an aldehyde and HCN catalysed by NaCN, which statements about the
fluoride
reaction mechanism are true?
38 For the reaction sodium lauryl sulphate

(CH3)3SiCl + C2H5O– → (CH3)3SiOC2H5 + Cl –

1 Adeductions
33 Ethylene
What new carbon-carbon
glycol, HOCH
about2the bondisisused
CH2properties
OH, formed.
of as
thisasubstance
de-icer. It can
allows
be ice to melt
made from at temperatures
this structure? below
0 °C.
2 Instatements
which the intermediate,
are likelythe oxygen
to be true?carried a negative charge.

B
1 Part of the structure is polar and is water–attracting.
Which
13 ItThe statements
last stageare correct?
involves by C2H5O–.
solublethe
attack formation
in oil droplets.of a hydrogen-oxygen bond.
involves nucleophilic
2 The alkyl chain is
1 Ethylene glycol changes
by C2H5Othe . extensive network of hydrogen bonds in ice.
– –
2 Cl is displaced
3 All the C-C-C bond angles are tetrahedral.

2
3 TheEthylene glycol molecules
oxygen-carbon bond isform hydrogen9701/1/O/N/02
not broken. bonds with other ethylene glycol molecules. [J‘03 Q32]
3 Ethylene
393 Modern cars glycol molecules
are fitted will dissolve
with catalytic in the water
converters. formed
These from the
remove ice. monoxide, unburnt
carbon
hydrocarbons and oxides of nitrogen from exhaust gases.

Which of these pollutant gases are removed by oxidation?

1 carbon monoxide
B
2 hydrocarbons
9701/1/M/J/03 [Turn over
3 nitrogen oxides

[N‘05 Q39]

© UCLES 2017
40 9701/13/M/J/17
The sex-attractant of the house-fly is muscalure, with the following formula. [Turn over

CH3(CH2)7CH = CH(CH2)12CH3

Which statements about muscalure are correct?

1 It will decolourise aqueous bromine.

2 It will be oxidised by cold aqueous alkaline KMnO4 to give a diol.
3 It will be optically active.

CEDAR COLLEGE 134 ALKANES WS 3

 3 With water, L forms a strong acid.
No other combination of statements is used as a correct response.

4 During the bromination of methane, the free radical CH3• is generated. A possible terminating
37
35 step
Whichof reactions involving
this reaction calcium and
is the formation of Cits
2H6compounds would produce
by the combination tworadicals.
of two free gaseous products?

1 heating
What solid
could be anhydrous
produced calcium nitrate
in a terminating step during the bromination of propane?
2 CH
heating solid anhydrous calcium carbonate
3
13
13 CH 3CH2CH2CHCH3
adding calcium metal to water
Section B
CH3

A
36 each
Which properties
questionsininthe
thissequence hydrogen
or more ofchloride,
the threehydrogen
numberedbromide and1 tohydrogen
3 may iodide
For 2steadily
CH 3CHCHCH
of the
increase? 3
section, one statements
be correct.
CH3
Decide1 whether
thermaleach
stability
of the statements is or is not correct (you may find it helpful to put a tick against
the statements that
2 bond lengthCH3 consider to be correct).
you

33 CH 3CH
The responses
ease A2CHCH
of to 2CH3 be selected on the basis of
D should
oxidation

[N‘08 Q39]
A B C D
5 Which compounds may result from mixing ethane and chlorine in the presence of sunlight?
37
1, 2 and 3 1 and 2 2 and 3 1 only
1 CH2Cl
CH3are only are only are is

A
correct correct correct correct
2 CH3CH2CH2CH3
3 combination
CH3CHCl CHCl CH3

No other of statements 14
is used as a correct response.
[N‘04 Q37]
The responses A to D should be selected on the
© UCLES 2013
basis of
9701/13/M/J/13 [Turn over
6 For complete combustion, 1 mol of an organic compound X was found to require 2.5 mol of
31
molecular oxygen.
A B C D

:
Which compounds could be X?
1, 2 and 3 1 and 2 2 and 3 1 only
1 C2H5OHare only are only are is
correct correct correct correct
2 C 2H 2

3 CH
No other 3CHO
combination of statements is used as a correct response.
[J‘08 Q31]

7 Catalysts
32
37 A fraction are used in crude
of distilled many oil
reversible
containsreactions
moleculesin with
the chemical
between industry.
15 and 19Vanadium(V) oxide
carbon atoms. is
This
used in this
fraction way in by
is cracked thestrong
Contact process for the formation of SO3.
heating.

Why is this done? 2SO2(g) + O2(g) 2SO3(g)

1 To
What produce
effect doesalkenes.
vanadium(V) oxide have on this equilibrium?
2
1 Tospeeds
It produce
upsmaller molecules
the forward which are in higher demand.
reaction.
3
2 Toincreases
It insert oxygen atoms
the value of into
Kp. the hydrocarbons.
© UCLES 2004 9701/01/O/N/04 [J‘09 Q37]
3 It increases the value of Ea for the reverse reaction.
38 Geraniol is one of several compounds produced by the scent glands of honey bees to help them
mark nectar-bearing flowers and locate the entrances to their hives.
33 Which statements about the properties of a catalyst are correct?
OH
1 A catalyst increases the average kinetic energy of the reacting particles.
2 A catalyst increases the rate of the reverse reaction.
geraniol
3 A catalyst has no effect on the enthalpy change of the reaction.
Which reactions will geraniol undergo?

1 reaction with hot concentrated acidic KMnO4 to give propanone

CEDAR
2 COLLEGE
addition of halogens 135 ALKANES WS 3

3 reaction with aqueous NaHCO3 to give CO2

© UCLES 2008 9701/01/M/J/08 [Turn over
 fertiliser.
2 A bleaching solution remains after the reaction.
1 A co-ordinate bond is formed.
33 Which are assumptions of the kinetic theory of gases and hence of the ideal gas equation,
3 The
Which final solution
reactions givesinathe
will occur precipitate with acidified silver nitrate.
treated soil?
PV
2 =ThenRT ?
oxidation number of nitrogen is unchanged.
+
1 Ca(OH)2 +acts
1 Molecules 2NHas
move (aq) Ca2+(aq) + with
→ interacting
4 without 2NH 3 + 2H
one 2O
another except for collisions.
8 In a car engine pollutant oxide Y, which contains
36
3 Ammonia a Brønsted-Lowry base. non-metallic element X, is formed.
+ 2+
22 Intermolecular
Ca(OH)2 + 2H forces(aq) →areCa negligible.
(aq) + 2H2O
Further oxidation of Y to Z occurs in the atmosphere. In this further oxidation, 1 mol of Y reacts
35 Compared0.5 molwith
Ca(OH) the2distances
HCl
2of+gaseous
3with Intermolecular CO molecule,
→ CaCO 3 + H
are
oxygen. the
2O bond
much ……X……
greater than theof the HBr molecule
molecular size. is ……Y……

Which
X couldpairs of words
be either correctly
nitrogen complete the above sentence?
or sulfur.
35 Use
Which of the halide ions,is chloride, bromide or iodide, acts as a reducing agent when its sodium

A
34 of the Data Booklet relevant to this question.
salt reacts with
Which statements concentrated sulfuric
X about X, Y and Z can acid?
Y be correct?
Which properties would –
be–expected –
for radium, 88Ra, or its compounds?
1
1 1 at
Theleast one ofnumber
energy
oxidation Cl , Br ofand I less by two from Y to Z.
X increases
1 Radium carbonate– would not decompose at the temperature of a Bunsen flame.
2
2 2 at leasthave
Y may two of
anCl
polarity , Br – and
unpaired I – less
electron in its molecule.
2 Radium hydroxide –
is very insoluble.
3 3 all
Y isthree of Cl , Br – and I –

length
a polar molecule. greater
3 Radium does not react with cold water.
[J‘11 12 Q36]

9 In
36
37
36 a carstatements
Which engine, non-metallic
compounds cantrue
are element
be obtained
about thefromX forms
Haberethenea pollutant
in a for
process singleoxide
the Y.
reaction?
manufacture of ammonia?
35 When a firework is lit, a fuel and an oxidising agent react together.
11 CH
Further 3 CH3 temperatures, the yield goes down but the rate of production of ammonia is faster.
oxidation of Y to Z occurs spontaneously in the atmosphere. In this further oxidation,
At higher
In oneofsuch
1 mol firework,
Y reacts withmagnesium is the fuel
0.5 mol of gaseous and barium nitrate is the oxidising agent.
oxygen.
22 At( higher
CH2 CH 2 )
pressures,
n
the yield goes down but the rate of production of ammonia is faster.
13
Which solids are produced
statements about X,when
Y andthe firework
Z are is lit?
correct?
3 HOCH2 CH2 OH
3 In the presence of a catalyst, the yield goes down but the rate of production of ammonia is

:
35 Solids
1 BaO W, X, aY basic
faster.
X forms and Zhydride.
are compounds of two different Group II metals. Some of their applications
are described below.
2 MgO Y is a diatomic molecule.
Compound
37 Which compounds W is used canasbea obtained
refractoryfromliningpropene
materialininakilns.
single reaction?

3 Mg(NO 3)2
Z is a polar molecule.
Compound
1 CH2OHCHOHCH X is used3 as a building material. It can also be heated in a kiln to form compound [N‘11 11 Q36]
Y.
When Y is hydrated, it forms compound Z which is used agriculturally to treat soils.
10
36
37 2In a(car
CHengine,
2CH(CHC
Disaccharides, non-metallic
3)12)Hn22O11, areelement X forms
important a pollutant
in the human oxide Y. example, sucrose is found in
diet. For
pastries
Which and lactose
statements occurs
about in milk
these products.
compounds are correct?
3 CH2BrCH
Further 2CH2Br
oxidation of Y to Z occurs spontaneously in the atmosphere. In this further oxidation,
molMore
11Both of these
of reacts
Y acid with 0.5 mol
is neutralised
compounds can ofbe
by 1gaseous
ghydrolysed.
of W thanoxygen.
by 1 g of X.

38 2What
The
Whicharemetallic
the same
statements
sucrose element
+forHa2O
about in→
YWof
pair
X, reacts
and
CH with
optical
Z are water more quickly than the metallic element in Y.
isomers?
correct?
2OH(CHOH)4CHO + CH2OH(CHOH)3COCH2OH

31 Adding Z to a soil
theiroxidation
The empirical decreases
formula
number the pH
of X increases ofbythe
glucose soil. Y to Z.
2 from fructose
© UCLES 2011 9701/12/M/J/11 [Turn over
2 The
theirmolecule
functional ofgroups
lactose Y+has
H 2Ono→ unpaired electrons.4CHO + CH2OH(CHOH)4CHO
CH2OH(CHOH)
36 When a red-hot platinum wire is plunged into a test tube of hydrogen iodide, the gas is
3 The
theirmolecule
decomposedstructural offormula
into its Z contains Ifthree
elements. glucose
the oxygen atoms.
experiment is repeated with hydrogen chloride, no change

galactose
occurs. [N‘11 12 Q36]
Which statements about these hydrolysis products are correct?
11 Which
39 Which factors
statements about to
contribute thethis
photochemical
behaviour? chlorination of ethane are correct?
1 Glucose and fructose have structural isomers.
11 the
c
Hydrogen
strength gas
of is
theone of the products. bond
hydrogen-halogen
2 Glucose and galactose are optical isomers.
A propagation
2 the step in the
size of the halogen mechanism is C2H6 + Cl • → C2H5• + HCl.
atom
3 Glucose and galactose are ketones.
Thestandard
3 the initiationenthalpy
step is theof homolytic
formation, fission
, ofofeach
chlorine.
of the products of decomposition

[J‘12 12 Q39]

12
37 Which molecules would be present in the mixture produced by the photochemical chlorination of
© UCLES 2012 9701/12/M/J/12 [Turn over
methane?
© UCLES 2011 9701/11/O/N/11 [Turn over

C
1 hydrogen
© UCLES 2011
2 hydrogen chloride 9701/12/O/N/11 [Turn over

3 dichloromethane

[J‘13 11 Q37]

38 In which reactions is the organic compound oxidised by the given reagent?

1 CH3CH2CHO + Fehling’s reagent

CEDAR
2 COLLEGE
CH3CH2CH2CHO + Tollens’ reagent 136 ALKANES WS 3

3 CH3CHO + 2,4-dinitrophenylhydrazine reagent

 ALKANES WS 4
4 A
SECTION For
Examiner’s
Use
21 A car can be considered to run on octane, C8H18.

(a) Write an equation for the complete combustion of octane.

Cry His t
12.502 →
802 + 9h20
......................................................................................................................................[1]

The composition of the exhaust gases (fumes) from a petrol (gasoline) engine is given
below.

Percentage
Gas by volume

carbon dioxide 9
water vapour 8
oxygen 4
hydrogen 2
carbon monoxide 3–6
hydrocarbons 0.2
nitrogen oxides 0.4–0.05

(b) (i) What gas, omitted from the table, makes up most of the remainder of the exhaust
fumes?

Nitrogen
...................................................................................................................................

(ii) Explain why there is always water vapour in the exhaust fumes.
water is formed as a result of the
...................................................................................................................................
combustion .
[2]

(c) (i) State two gases in the exhaust fumes which are poisonous to humans. Also state
briefly for each the particular effect on humans.
Carbon monoxide
gas I ..........................................................................................................................
with
Bonds
haemoglobin
to
fatally reduce
effect .........................................................................................................................
NO I
absorption of 02
gas II .........................................................................................................................
causes
respiratory problems
effect .........................................................................................................................

(ii) The two gases you have given in (c)(i) can be removed by reaction in a platinised
catalytic converter. The products of the reaction in the converter are not hazardous.
For each of your gases in (c)(i) give an equation which shows how it is removed to
form less harmful substances.

CO t 11202 → CO2
I .................................................................................................................................
NO t Hz → H2O t
42142
II ................................................................................................................................

CEDAR COLLEGE 137 ALKANES WS 4

9701/02/O/N/03
 5 For
Examiner’s
Use
(iii) Suggest one reason why the exhaust fumes from a car fitted with a catalytic
converter are still hazardous to human health to some degree.
There is much CO removed
too to
completely
be .

...................................................................................................................................
OR .

...................................................................................................................................
2
Some 802 parser through and causes acid rain
...............................................................................................................................[5]
Answer all the questions in the space provided. For
[W‘03 Q2] Examiner’s
[Total : 8]
12 Most submarines travel under water using electrical power from batteries. The German Use

engineer Helmut Walter designed a diesel engine that could be used to propel a submarine
beneath the surface of the sea. Instead of taking air from above the surface of the sea,
Walter’s engine used hydrogen peroxide, H2O2, to provide oxygen for a conventional diesel
engine.

Hydrogen peroxide may be catalytically decomposed to give water and oxygen.

(a) (i) What is meant by the term catalyst?

..................................................................................................................................

..................................................................................................................................

(ii) Construct a balanced equation for the decomposition of H2O2.

............................................................................................................................. [3]

Diesel fuel may be considered to consist of the hydrocarbon C15H32 which reacts completely
with oxygen according to the following equation.

C15H32 + 23O2 → 15CO2 + 16H2O

(b) (i) To which homologous series does C15H32 belong?

................................................

(ii) Use the equation above and your answer to (a)(ii) to calculate the amount, in moles,
of H2O2, that will provide sufficient oxygen for the complete oxidation of one mole
of C15H32.

amount of H2O2 = ................................. mol

[3]

CEDAR COLLEGE 138

9701/02/O/N/03
ALKANES WSover
[Turn 4
 3

A submarine equipped with a Walter engine used 212 tonnes of diesel fuel during an For
underwater voyage. The submarine also carried concentrated aqueous H2O2. Examiner’s
[1 tonne = 106 g] Use

(c) (i) Calculate the amount, in moles, of diesel fuel used during the underwater voyage.

amount of diesel fuel = ................................. mol

(ii) Use your answers to (b)(ii) and (c)(i) to calculate the mass, in tonnes, of hydrogen
peroxide used during the underwater voyage.

mass of H2O2 = ................................. tonnes

[4]

(d) The exhaust products of the Walter engine were passed into the sea.

What would happen to them?

..................................................................................................................................... [1]
[W‘08 Q1]
[Total: 11]

© UCLES 2008 9701/02/O/N/08 [Turn over

CEDAR COLLEGE 139 ALKANES WS 4

 ⑧ The sub uses Hzoz to
get 02 so the fuel

com burn .

burn
Questions
asking
how much HPa is required to

I Md of the diesel ( Go Hss )

required
to burn
need out how much 02 is
figure
First to
Ii) I

combustion
Cis Has
completely
.
I use the
hydrocarbon eg .

Cx ( H2O
£
02 CO2
Ly )
t Xt → t
Hy x

x = 15

32
y
=
.

2) 15 23
tf
X t
y
= =
=
32g
.

,
,

( 15h32 : 02

23
°

I . .

ii If out how much H2O , is

required to produce 23 and of 02
figure
I .
. .

that'll be the same amount of HD2 required to

produce
02 to combust I met of Cis Hzz
enough
.

02 : H2O ,
⑤
I
2
°

: 46
23

I
✓

46 moles are required to

produce
23 moles of 02 .
.
.

that 'll burn I mole of cis Azz .

Fant
 of deisel
② pretty
much moles in 212 tonnes .

45 Azz burnt
212 tonnes of was .

⑧
45432 : H 202

tonnes 212 : ?

ratio 46
°

more I .

1000,000 4600,000 moles

mores present → .

all
maths tells I need 46 million motel of HD2 to burn
simple me

denise
my
.

46,000,000 motel in mass =

46,000,000 x ( Mr of Hzoz)

46,000,000×1341=1.564×109

divided 106
g. y by

1564 tonnes
=
 7

3 (b) (i) By using equations, describe the mechanism of the reaction between chlorine and For
methane to form chloromethane, CH3Cl. Examiner’s
Use
Identify, by name, the separate steps of the overall reaction.

..................................................................................................................................
Mr au .

Initiation :
Cl Cl
-
2cL .

..................................................................................................................................
-

:O Hzc HCl
.
→ +
Propagation
. .

..................................................................................................................................
② itzc.hr#1-cHzUt Cl
..................................................................................................................................
.

Termination : Cl .MG → 2cL .

..................................................................................................................................

..................................................................................................................................

(ii) What is the intermediate organic species in this reaction?

CHS
.

.............................................. [7]

(c) The energy of activation for the formation of CH3Cl is 16 kJ mol–1.

Use this figure and your answer to (a)(i) to complete the reaction pathway diagram
below showing the formation of CH3Cl from CH4 and Cl2.
Show clearly the intermediate organic species and the final products.
Indicate on your sketch the relevant enthalpy changes and their values.

enthalpy

CH4 + Cl 2
HCl
AH CHU t .

progress of reaction
[4]
[W’09 21 Q3]
[Total: 16]

© UCLES 2009 9701/21/O/N/09 [Turn over

CEDAR COLLEGE 140 ALKANES WS 4

 2

Answer all the questions in the space provided. For

Examiner’s
1 4 In 1814, Sir Humphrey Davy and Michael Faraday collected samples of a flammable gas, A, Use

from the ground near Florence in Italy.

They analysed A which they found to be a hydrocarbon. Further experiments were then
carried out to determine the molecular formula of A.

(a) What is meant by the term molecular formula?

..........................................................................................................................................

..........................................................................................................................................

...................................................................................................................................... [2]

Davy and Faraday deduced the formula of A by exploding it with an excess of oxygen and
analysing the products of combustion.

(b) Complete and balance the following equation for the complete combustion of a
hydrocarbon with the formula CxHy .

CxHy + x + ( y
)
O
4 2
................................ + ................................
[2]

(c) When 10 cm3 of A was mixed at room temperature with 50 cm3 of oxygen (an excess)
and exploded, 40 cm3 of gas remained after cooling the apparatus to room temperature
and pressure.
When this 40 cm3 of gas was shaken with an excess of aqueous potassium hydroxide,
KOH, 30 cm3 of gas still remained.

(i) What is the identity of the 30 cm3 of gas that remained at the end of the
experiment?

...................................................

(ii) The combustion of A produced a gas that reacted with the KOH(aq).

What is the identity of this gas?

...................................................

(iii) What volume of the gas you have identified in (ii) was produced by the combustion
of A?

...............................cm3

(iv) What volume of oxygen was used up in the combustion of A?

...............................cm3 [4]

© UCLES 2010 9701/21/O/N/10

CEDAR COLLEGE 141 ALKANES WS 4

 3

(d) Use your equation in (b) and your results from (c)(iii) and (c)(iv) to calculate the For
molecular formula of A. Examiner’s
Show all of your working. Use

[3]
[W‘10 21 Q1]
[Total: 11]

© UCLES 2010 9701/21/O/N/10 [Turn over

CEDAR COLLEGE 142 ALKANES WS 4

 6

35 Crude oil is a naturally occurring flammable liquid which consists of a complex mixture of For
hydrocarbons. In order to separate the hydrocarbons the crude oil is subjected to fractional Examiner’s
distillation. Use

(a) Explain what is meant by the following terms.

(i) compound containing only

C Md
hydrocarbon .............................................................................................................

It
..................................................................................................................................

(ii) separation of comp bonds

by
fractional distillation ..................................................................................................

their
boiling points
..............................................................................................................................
.

[2]

(b) Undecane, C11H24, is a long chain hydrocarbon which is present in crude oil.
Such long chain hydrocarbons are ‘cracked’ to produce alkanes and alkenes which have
smaller molecules.

(i) Give the conditions for two different processes by which long chain molecules
may be cracked.
and
High temperature high
process 1 ..................................................................................................................

pressure
..................................................................................................................................
.

and
High pressure a
catalyst
process 2 ..................................................................................................................

..................................................................................................................................

(ii) Undecane, C11H24, can be cracked to form pentane, C5H12, and an alkene.
Construct a balanced equation for this reaction.

Cll H 24 → C 5h12 t
2cg Hb
.............................................................................................................................. [3]

Pentane, C5H12, exhibits structural isomerism.

(c) (i) Draw the three structural isomers of pentane.

CH3
I

Chest
CHS
CHzCHzCHzCHzCH3 CH3CHzCftCH3
-

CHL CH3

isomer B isomer C isomer D

© UCLES 2010 9701/21/O/N/10

CEDAR COLLEGE 143 ALKANES WS 4

 For
(ii) Use relevant data from the Data Booklet to calculate the amount of heat released in Examiner’s
this experiment. Use
7

(ii) The three isomers of pentane have different boiling points. For
Examiner’s
Which of your isomers has the highest boiling point? Use

isomer .........
(iii) Use the data above and your answers to (i) and (ii) to calculate the energy produced
by the burning
Suggest of 1 mol offor
an explanation propane.
your answer.

..................................................................................................................................

..................................................................................................................................

[5]
.............................................................................................................................. [6]

The unsaturated hydrocarbon, E, is obtained by cracking hexane and is important in the

chemical
(e) industry.
The boiling points of methane, ethane, propane, and butane are given below.

The standard enthalpy change of combustion of E is –2059 kJ mol–1.

compound CH4 CH3CH3 CH3CH2CH3 CH3(CH2)2CH3
(d) Define the term
boiling pointstandard
/K enthalpy
112 change of 185
combustion. 231 273

..........................................................................................................................................
(i) Suggest an explanation for the increase in boiling points from methane to butane.

...................................................................................................................................... [2]
....................................................................................................................................
When 0.47 g of E was completely burnt in air, the heat produced raised the temperature of
....................................................................................................................................
200 g of water by 27.5 °C. Assume no heat losses occurred during this experiment.
....................................................................................................................................
(e) (i) Use relevant data from the Data Booklet to calculate the amount of heat released
in this experiment.
(ii) The isomer of butane, 2-methylpropane, (CH3)3CH, has a boiling point of 261 K.
Suggest an explanation for the difference between this value and that for butane in
the table above.

....................................................................................................................................
(ii) Use the data above and your answer to (i) to calculate the relative molecular mass,
....................................................................................................................................
Mr, of E.

....................................................................................................................................
[4]
[W‘10 22 Q3]
[Total: 15]
[4]

(f) Deduce the molecular formula of E.

[1]

[Total: 18]

© UCLES 2013 9701/21/O/N/13 [Turn over

© UCLES 2010 9701/21/O/N/10 [Turn over

CEDAR COLLEGE 144 ALKANES WS 4

 4

26 Crude oil contains a mixture of hydrocarbons together with other organic compounds which For
may contain nitrogen, oxygen or sulfur in their molecules. Examiner’s
Use

At an oil refinery, after the fractional distillation of crude oil, a number of other processes may
be used including ‘cracking’, ‘isomerisation’, and ‘reforming’.

(a) (i) What is meant by the term ‘cracking ’ and why is it carried out?

..................................................................................................................................

..................................................................................................................................

..................................................................................................................................

..................................................................................................................................

(ii) Outline briefly how the cracking of hydrocarbons would be carried out.

..................................................................................................................................

..................................................................................................................................

(iii) Construct a balanced equation for the formation of heptane, C7H16, by cracking
tetradecane, C14H30.

..................................................................................................................................
[4]

One of the sulfur-containing compounds present in crude oil is ethanethiol, C2H5SH, the
sulfur-containing equivalent of ethanol. Ethanethiol is toxic and is regarded as one of the
smelliest compounds in existence.

(b) The boiling point of ethanol, C2H5OH, is higher than that of C2H5SH.
Suggest a reason for this difference.

..........................................................................................................................................

...................................................................................................................................... [1]

© UCLES 2011 9701/21/M/J/11

CEDAR COLLEGE 145 ALKANES WS 4

 5

When ethanethiol is burned in an excess of air, three oxides of different elements are For
formed. Examiner’s
Use

(c) (i) Construct a balanced equation for this reaction.

..................................................................................................................................

(ii) Two of the oxides formed cause serious environmental damage.

For each of these oxides, identify the type of pollution caused and describe one
consequence of this pollution.

..................................................................................................................................

..................................................................................................................................

..................................................................................................................................

..................................................................................................................................

..................................................................................................................................
[6]

(d) A small amount of ethanethiol is added to liquefied gases such as butane that are widely
used in portable cooking stoves.

Suggest a reason for this.

...................................................................................................................................... [1]

Sulfur-containing compounds are removed from oil products at the refinery. The sulfur is
recovered and converted into SO2, which is then used in the Contact process.

(e) State the main operating details of the formation of SO3 in the Contact process.

..........................................................................................................................................

..........................................................................................................................................

..........................................................................................................................................

..........................................................................................................................................

...................................................................................................................................... [3]

[Total: 15]
[S‘11 21 Q2]

© UCLES 2011 9701/21/M/J/11 [Turn over

CEDAR COLLEGE 146 ALKANES WS 4
 8
For
57 Propane, C3H8, and butane, C4H10, are components of Liquefied Petroleum Gas (LPG) which Examiner’s
is widely used as a fuel for domestic cooking and heating. Use

(a) (i) To which class of compounds do these two hydrocarbons belong?

......................................................

(ii) Write a balanced equation for the complete combustion of butane.

....................................................................................................................................
[2]

(b) When propane or butane is used in cooking, the saucepan may become covered by a
solid black deposit.

(i) What is the chemical name for this black solid?

......................................................

(ii) Write a balanced equation for its formation from butane.

....................................................................................................................................
[2]
[W‘13 21 Q5]

(c) Propane and butane have different values of standard enthalpy change of combustion.

Define the term standard enthalpy change of combustion.

...........................................................................................................................................

...........................................................................................................................................

..................................................................................................................................... [2]

(d) A 125 cm3 sample of propane gas, measured at 20 °C and 101 kPa, was completely burnt
in air.
The heat produced raised the temperature of 200 g of water by 13.8 °C.
Assume no heat losses occurred during this experiment.

(i) Use the equation pV = nRT to calculate the mass of propane used.

© UCLES 2013 9701/21/O/N/13

CEDAR COLLEGE 147 ALKANES WS 4

 4
For
28 Petrol and diesel fuel are both used in internal combustion engines. Examiner’s
Petrol may be regarded as having the formula C9H20 and diesel fuel as having the formula Use
C14H30.

(a) (i) To which class of compounds do these two hydrocarbons belong?

......................................................

(ii) Write a balanced equation for the complete combustion of petrol.

....................................................................................................................................
[2]

(b) When petrol or diesel fuel are used in internal combustion engines, several different
products of the incomplete combustion of the fuel may be formed.

(i) Name two of these products that do not contain hydrogen.

.................................. and ..................................

(ii) Choose one of these and state a hazard it causes.

product .......................................................................................................................

hazard ........................................................................................................................

(iii) Write a balanced equation for the formation of one of the products in (i) from diesel
fuel.

....................................................................................................................................
[4]
[W‘13 23 Q2]

© UCLES 2013 9701/23/O/N/13

CEDAR COLLEGE 148 ALKANES WS 4