1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20

atomic number

What is the property?

A atomic radius MCQ MADNESS 2

B first ionisation energy
C ionic radius SECTION A
D melting point
1 [N’09 p11 q13]

13 Which statement correctly describes what happens when silicon tetrachloride is added to water?

A The SiCl4 dissolves to give a neutral solution only.

B The SiCl4 reacts to give an acidic solution only.
C The SiCl4 reacts to give a precipitate and an acidic solution.
D The SiCl4 reacts to give a precipitate and a neutral solution.

14 The oxide and chloride of an element X are separately mixed with water. The two resulting
solutions have the same effect on litmus.
2 [N’09 p11 q18] 9
What is element X?
18 Most modern cars are fitted with three-way catalytic converters in the exhaust system.
A sodium
Which three gases are removed by such a catalytic converter?
B magnesium
A carbon monoxide, hydrocarbons, nitrogen oxides
C aluminium
B carbon monoxide, carbon dioxide, nitrogen oxides
D phosphorus
C carbon monoxide, nitrogen oxides, sulfur dioxide
D hydrocarbons, nitrogen oxides, sulfur dioxide

19 In an historically famous experiment Wöhler heated ‘inorganic’ ammonium cyanate in the

absence of air. The only product of the reaction
© UCLES 2009
was ‘organic’ urea, CO(NH2)2. No other
9701/11/O/N/09
products
[Turn over
were formed in the reaction.

What is the formula of the cyanate ion present in ammonium cyanate?

A CNO– B CNO2– C CO– D NO–

20 The drug cortisone has the formula shown.

CH2OH

CO
CH3 OH
O
CH3

In addition to those chiral centres marked by an asterisk (*), how many other chiral centres are
present in the cortisone molecule?

A 0 B 1 C 2 D 3
3 [N’09 p11 q21] 10

21 The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision.

The structure of retinal includes an aldehyde group, a cyclohexene ring and a long aliphatic side
chain, in which a carbon-carbon double bond exists between carbons numbered 11 and 12.

Which pair of statements about 11-cis retinal could be correct?

arrangement around
total number of
the adjacent carbons
>C=C< double bonds
11 and 12
R1 R2
A 5 C C
H H
R1 H
B 5 C C
H R2

R1 R2
C 6 C C
H H
R1 H
D 6 C C
H R2

22 What is the least number of carbon atoms in a non-cyclic alkane molecule that has a chiral
centre?

A 7 B 8 C 9 D 10

23 The following diagram represents the structure of a possible polymer.

OH OH OH OH OH OH

C C C C C C

H H H H H H

By which method might this polymer be made?

A polymerise ethene followed by hydration

B polymerise ethene followed by oxidation with cold acidified KMnO4
C polymerise 1,2-dichloroethene followed by hydrolysis
D polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO4

© UCLES 2009 9701/11/O/N/09

4 [N’09 p11 q29] 13
5
29 The characteristic odour of rum is attributed to the compound 2-ethyl-3-methylbutanoic acid.
9 Four reactions of the type shown are studied at the same temperature.
CH3 C2H5
X (g) + Y (g) → Z (g)
H 3C C C C OH
Which is the correct reaction pathway diagram for the reaction that would proceed most rapidly
and with the highest yield? H H O

A 2-ethyl-3-methylbutanoic acid B
Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with
alcoholic sodium cyanide and subsequent acid hydrolysis of the reaction product?

CH3
energy energy
A CH3 CH CH2 CHBr CH3

CH3

B reactant product reactant product

CH3 CH CHBr CH2 CH3

CH3 C 2 H5 C D

C CH3 CH CH CH2Br

CH3 CH2Br
energy energy
D CH3 CH CH2 CH CH3

30 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be
reactantwith acid.
product reactant product
5 [N’09 p12 q10]
destroyed by hydrolysis

CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C H
10 Photochromic glass, used for sunglasses, darkens when exposed to bright light and becomes
more transparent again when the light is less bright. The depth O
of colour of the glass is related to
the concentration of silver atoms.
A simplified formula for lardolure may be written as follows.
The following reactions are involved.
RCH(CH 3)O C H
reaction 1 Ag+ + Cl – Ag + Cl
O
reaction 2 Cu+ + Cl → Cu2+ + Cl –
What are the productsreaction Cu2+ + Ag → Cu+ + Ag+
of its hydrolysis?
3
A RCH(CH
Which 3)CO
statement 2H + CH
about 3OH
these reactions is correct?
B RCH(CH3)CO 2+ 2H + HCO2H
A Cu+ and Cu ions act as catalysts.
C RCH(CH )OH + CO2
B Cu+ ions 3act as an oxidising agent in reaction 2.
D RCH(CH )OH + HCO H
C Reaction 32 is the one 2in which light is absorbed.
D Ag+ ions are oxidised in reaction 1.

© UCLES 2009 9701/11/O/N/09 [Turn over

© UCLES 2009 9701/12/O/N/09 [Turn over
 A atomic radius
B first ionisation energy
C ionic radius
D melting point
6 [N’09 p12 q12]

12 Which statement correctly describes what happens when silicon tetrachloride is added to water?

A The SiCl4 dissolves to give a neutral solution only.

B The SiCl4 reacts to give an acidic solution only.
C The SiCl4 reacts to give a precipitate and an acidic solution.
D The SiCl4 reacts to give a precipitate and a neutral solution.

13 The oxide and chloride of an element X are separately mixed with water. The two resulting
7 [N’09 p12 q20]
solutions have the same effect on litmus.
9
What is element X?
20 The presence of 11-cis retinal, C20H28O, in cells in the eye is important for vision.
A sodium
The structure of retinal includes an aldehyde group, a cyclohexene ring and a long aliphatic side
B magnesium
chain, in which a carbon-carbon double bond exists between carbons numbered 11 and 12.
C aluminium
Which pair of statements about 11-cis retinal could be correct?
D phosphorus
arrangement around
total number of
the adjacent carbons
>C=C< double bonds
11 and 12
R1 R2
A 5 C C
© UCLES 2009 H H
9701/12/O/N/09

R1 H
B 5 C C
H R2

R1 R2
C 6 C C
H H
R1 H
D 6 C C
H R2

21 What is the least number of carbon atoms in a non-cyclic alkane molecule that has a chiral
centre?

A 7 B 8 C 9 D 10

22 The following diagram represents the structure of a possible polymer.

OH OH OH OH OH OH

C C C C C C

H H H H H H

By which method might this polymer be made?

A polymerise ethene followed by hydration

B polymerise ethene followed by oxidation with cold acidified KMnO4
C polymerise 1,2-dichloroethene followed by hydrolysis
D polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO4
8 [N’09 p12 q28] 12

28 The characteristic odour of rum is attributed to the compound 2-ethyl-3-methylbutanoic acid.

CH3 C2H5

H 3C C C C OH

H H O
2-ethyl-3-methylbutanoic acid

Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with
alcoholic sodium cyanide and subsequent acid hydrolysis of the reaction product?

CH3

A
8
CH3 CH CH2 CHBr CH3
18 Mohr’s salt is a pale green crystalline solid which is soluble in water. It is a ‘double sulfate’ which
contains twoCH 3
cations, one of which is Fe2+.

B
The CH 3
identity CH
of the CHBr CH2 was
second cation CHdetermined
3 by heating solid Mohr’s salt with solid sodium
hydroxide and a colourless gas was evolved. The gas readily dissolved in water giving an alkaline
CH3 C2H5
solution. A grey-green solid residue was also formed which was insoluble in water.

C CH3 CH CH CH2Br
What are the identities of the gas and the solid residue?

gas residue
CH3 CH2Br
A H2 FeSO4
D CH3 CH CH2 CH CH3
B NH3 Na2SO4
C NH3 Fe(OH)2
29 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be
D
destroyed bySO 2
hydrolysis Fe(OH)
with acid. 2
9 [J’09 p11 q19]
CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C H
19 In recent years a number of athletes have been banned from sports because of their illegal use of
synthetic testosterone, a naturally occurring hormone in the body.O

OH
CH
A simplified formula for lardolure may be written as follows.
3

RCH(CH3)O C H
CH3
O

What are the products of its hydrolysis?

O
A RCH(CH3)CO2H + CH3OH
testosterone
B RCH(CH3)CO2H + HCO2H
How many chiral centres are present in a testosterone molecule?
C RCH(CH3)OH + CO2
A
D 1
RCH(CH3)OH +BHCO
2H C 3 D 6
2

20 The compound known as ‘gamma-linolenic acid’ is found in significant amounts in the seeds of
the Evening Primrose plant. There is evidence that the compound may help patients with
diabetes.
© UCLES 2009
CH3(CH2)4CH=CHCH29701/12/O/N/09
CH=CHCH2CH=CH(CH2)4CO2H
gamma-linolenic acid

How many cis-trans isomers does gamma-linolenic acid have?

A 3 B 6 C 8 D 12
 B adding warm aqueous sodium hydroxide to 2-bromopropane
testosterone
C adding warm ethanolic sodium hydroxide to 1-bromopropane
Howpassing
D many chiral centresvapour
propan-2-ol are present in a testosterone
over heated aluminiummolecule?
oxide
A 1 B 2 C 3 D 6
10
26 [J’09 p11
Glycol, q20]
used in anti-freeze, has the formula HOCH2CH2OH. It can be oxidised to give a number of
products.
20 The compound known as ‘gamma-linolenic acid’ is found in significant amounts in the seeds of
the Evening
What Primroseformula
is the molecular plant. ofThere is evidence
an oxidation that
product the compound
of glycol may
that will not help
react withpatients
sodium?with
diabetes.
A C 2H 2 O2 B C 2H 2 O3 C C 2H 2 O4 D C 2H 4 O2
CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H
gamma-linolenic acid
27 Which ester is formed when the alcohol CH3CH2OH is reacted with CH3CH2CH2CO2H?
Howethyl
A many cis-trans isomers does gamma-linolenic acid have?
propanoate
A
B 3
ethyl butanoate B 6 C 8 D 12

C propyl ethanoate
D butyl ethanoate
11 [J’09 p11 q28]
28 Carvone gives the characteristic flavour to caraway and spearmint.

O
© UCLES 2009 9701/01/M/J/09 CH3

H3C
C

CH2

carvone

Prolonged heating of carvone with hot concentrated acidified potassium manganate(VII)

produces carbon dioxide and a compound X.

X contains nine carbon atoms and reacts with 2,4-dinitrophenylhydrazine reagent.

What is the maximum number of molecules of 2,4-dinitrophenylhydrazine that will react with one
molecule of X?

A 1 B 2 C 3 D 4

© UCLES 2009 9701/01/M/J/09

 Titanium(IV) oxide, TiO2, is brilliantly white and much of the oxide produced is used in the
manufacture of paint.

What is the maximum amount of TiO2 obtainable from 19.0 tonnes of the ore ilmenite, FeTiO3?

A 10.0 tonnes B 12.7 tonnes C 14.0 tonnes D 17.7 tonnes

12 [N’08 p11 q2]
2 Carbon disulphide vapour burns in oxygen according to the following equation.

CS2(g) + 3O2(g) → CO2(g) + 2SO2(g)

A sample of 10 cm3 of carbon disulphide was burned in 50 cm3 of oxygen. After measuring the
volume of gas remaining, the product was treated with an excess of aqueous sodium hydroxide
and the volume of gas measured again. All measurements were made at the same temperature
and pressure, under such conditions that carbon disulphide was gaseous.

What were the measured volumes?

3
volume of gas volume of gas after
3
after burning / cm adding NaOH(aq) / cm3
5 Which quantity would best indicate the relative strengths of the hydrogen bonds between the
molecules
A in liquid 30
hydrogen halides? 0
A B bond dissociation
30 energies 20
B C enthalpy changes
50 of solution 20
C D enthalpy changes
50 of formation 40
D enthalpy changes of vaporisation
3 In which pair do both atoms have one electron only in an s orbital in their ground states?

136 [N’08
A
p11
Ca, Scq5]
A substance commonly
B found in the house
Cu, Be C or H,
garden
3 He
has the D
following
Li, Crproperties.
• It is combustible.
5 Which quantity would best indicate the relative strengths of the hydrogen bonds between the
4 Use of •theItin
molecules Data anBooklet
isliquid is insulator.
hydrogen
electrical relevant to this question.
halides?

AHardbond
water contains
It melts overcalcium
• dissociation a range ions
energies and hydrogencarbonate ions arising from dissolved calcium
of temperature.
hydrogencarbonate, Ca(HCO3)2.
B
Whatenthalpy
could thechanges of solution
substance be?
How many electrons are present in the hydrogencarbonate anion?
C
A enthalpy
brass changes of formation
A 30 B 31 C 32 D 33
D
B enthalpy
paper changes of vaporisation
C poly(ethene)
6 A substance commonly found in the house or garden has the following properties.
D silicon(IV) oxide
14 [N’08 p11
• Itq7]
is combustible.
7© UCLES
Which of the following would behave most9701/01/O/N/08
2008• It is an electrical insulator.
like an ideal gas at room temperature?

A carbon
• It dioxide
melts over a range of temperature.
B helium
What could the substance be?
C hydrogen
A brass
D nitrogen
B paper
C poly(ethene)
8 Red lead oxide, Pb3O4, is used in metal priming paints. It can be made by heating PbO in air.
D silicon(IV) oxide
6PbO(s) + O2(g) → 2Pb3O4(s)

7 Which of
twothe following
values would behave
are needed mostthe
to calculate likeenthalpy
an ideal change
gas at room temperature?
for this reaction?

A carbon
enthalpydioxide
change of combustion of lead and enthalpy change of formation of Pb3O4
B helium
enthalpy change of combustion of PbO and enthalpy change of formation of Pb3O4
C hydrogen
enthalpy change of formation of PbO and enthalpy change of atomisation of O2
D enthalpy change of formation of PbO and enthalpy change of formation of Pb3O4
nitrogen

8 Red lead oxide, Pb3O4, is used in metal priming paints. It can be made by heating PbO in air.
 A CH3CH(OH)CO2H
B CH3CH2CH2CO2H
10
C (CH3)2CHCONH2
24 Mevalonic
D (CH3)2acid, 3,5-dihydroxy-3-methylpentanoic
C(OH)CO acid, is involved in cholesterol formation in the
2H
15 [N’08
body. p11
It is q30]
an oil that occurs as a mixture of the two interchanging molecules shown in the
diagram.
30 Use of the Data Booklet is relevant to this question.
HO CH3 HO CH3
C
C
Ethyl ethanoate can be obtained from ethanoicI acid and ethanol by the following reaction.
CH2 CH2
CH2 CH2
CH3CH2OH + CH3CO2H II CH3CO2CH 2CH3 +CH2O
CH 2
CH2OH CO2H O
Ethanol (30 g) and ethanoic acid (30 g) are heated under refluxO together, and 22 g of ethyl
ethanoate are obtained.
What names are used to describe the pair of interchanging reactions I and II?
What is the yield of the ester?
A condensation and addition
A
B 25 %
dehydrogenationBand38 %
hydrogenation C 50 % D 77 %
11
C esterification and hydrolysis
27 Compound X
D neutralisation and acidification
16 [J’08 p11 q25]
• has the molecular formula C10H14O;
is unreactive
25 Halogenoalkanes are• important towardsinmild
molecules oxidising
organic agents.reactions. In particular they
synthetic
undergo a range of nucleophilic reactions.
What
© UCLES is the structure of the compound formed
2008 by dehydration of X?
9701/01/O/N/08
Which reaction proceeds only by an SN1 mechanism?
A B
A CH3CH2Br + NH3
CH2 CH2 CH CH2 CH2 CH CH CH3
B CH3CH2CH2I + OH–
C CH3CHBrCH3 + NH3
C D
D (CH3)3CI + OH–
CH3 CH3

26 CHformula
An alcohol of molecular CH CCH
4H10 C CH CH3
2 O2 contains two OH groups and has an unbranched carbon
atom chain.
17 [J’08 p11 q28]
On reaction with an excess of hot MnO− / H+ this alcohol is converted into a compound of
28 Ethanal, CH3CHO, can be reduced using4 an aqueous methanolic solution of NaBH4 as the
molecularagent.
reducing formula C4H6O4.

To which
This two carbon addition
is a nucleophilic atoms inreaction.
the chain of the alcohol are the two OH groups attached?

A 1st and 2nd

What could be the first step of this mechanism?
B 1st and 3rd
A attack of an H+ ion at the carbon atom of the carbonyl group
C 1st and 4th
B attack of an H+ ion at the oxygen atom of the carbonyl group
D 2nd and 3rd
C attack of an H– ion at the carbon atom of the carbonyl group
D attack of an H– ion at the oxygen atom of the carbonyl group

29 Which compound is both chiral and acidic?

A B C D

H CO2H CH3 OH CH2Br CH(OH)CO2H

© UCLES 2008
C HCO2CH
9701/01/M/J/08
CH2CO2H
C CH3
H CO2H
 B Br2(g) → 2Br(g)

1
C 2
Br2(l) → Br(g)

1
D 2
Br2(g) → Br(g)
18 [N’07 p11 q9] 7

9 Which
19 In an molecules,
experiment,each cm3aoflinear
50.0with a 0.10 mol dm
carbon –3
chain, solution
can have of an
a metallic
optically salt reacted
active exactly with
isomer?
3 –3
25.0 cm of 0.10 mol dm aqueous sodium sulphite.
I II III IV
The half-equation for oxidation of sulphite ion is shown below.
C3 H6 BrI C3 H4 BrI C3 H6 I 2 C3 H4 Br2
SO 32− (aq) + H2O(I) → SO 24− (aq) + 2H+(aq) + 2e–
A I and II only
BIf the
I, IIoriginal
and III oxidation
only number of the metal in the salt was +3, what would be the new oxidation
number of the metal?
C II and III only
A +1 B +2 C +4 D +5
D I, II and IV only

10 Nitrogen dioxide decomposes on heating according to the following equation.

20 In which pair do the isomers have identical boiling points?
19 [N’07 p11 q19] 2NO2(g) 2NO(g) + O2(g)
A CH3 CH2 CH2 CH2 OH and (CH3 )2 CHCH2 OH
7

19 Which 4 mol of nitrogen

When molecules, each withdioxide
a linearwere
carbonputchain,
into acan dm3 container
1 have an opticallyand heated
active to a constant
isomer?
temperature, the equilibrium mixture contained 0.8 mol of oxygen.
B CH3 (CH2 )4 CH3 andI (CH3 )2 CHCH(CH II 3 )2 III IV
What is the value of the equilibrium constant, Kc, at the temperature of the experiment?
C3 H6 BrI C3 H4 BrI C3 H6 I 2 C3 H4 Br2
2
A 0 .8 ×CH 0 .8 B 1 .6 × 0 .8 CCH 1 .6 2 × 0 . 8 2
D 1 .6 × 20 .8
2 3 2 3 2
A I and4 II only 2 .4 4 2 .4
C H C and C H
B I, II and III only
Cl CH Cl Cl H 2 C Cl
C II and III only 2
I, II and IV only H
CH3 CH3 CH3
D

D C C and C C
H H H
20 In which pair do the isomers have identical boiling points?
CH3
20© UCLES
[N’07
A CH p11
2007
q21]
3 CH2 CH2 CH2 OH and (CH3 )2 CHCH2 OH
9701/01/O/N/07

21 Tetramethyl-lead(IV), (CH3 )4 Pb, increases the rate of the reaction of methane with chlorine.
B CH3 (CH2 )4 CH3 and (CH3 )2 CHCH(CH3 )2
CH4 (g) + Cl2 (g) → CH3 Cl(g) + HCl(g)

CH3 CH3
Why can tetramethyl-lead(IV) behave in this way?

C C and C
A It is a source of methyl radicals.
H H
B ItClreleasesCH
CHCl
+
(g) . Cl H 2 C Cl
23

C It reacts with chloromethane and prevents equilibrium being established.

CH3 H CH CH3
D Metal ions catalyse the reaction.3
D C C and C C
H CH3 H H

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?

© UCLES
A 2007
It is a source of methyl radicals. 9701/01/O/N/07 [Turn over

B It releases CH3+ (g) .

C It reacts with chloromethane and prevents equilibrium being established.

D Metal ions catalyse the reaction.
21 [N’07 p11 q28] 10

28 Hept-4-enal is present in cow’s milk.

CH3 CH2 CH=CHCH2 CH2 CHO

hept-4-enal

What is formed when hept-4-enal is reduced with either hydrogen and a nickel catalyst or
sodium borohydride?

A with H2 / Ni CH3 (CH2 )5 CH2 OH

B with H2 / Ni CH3 (CH2 )5 CH3
C with NaBH4 CH3 (CH2 )5 CH2 OH
D with NaBH4 CH3 (CH2 )5 CHO

29 Which of these reactions is shown by butanone, CH3 COCH2 CH3 ?

22 [J’07
A On p11 q17] with acidified potassium dichromate(VI)
warming 8 the solution turns green.

17 BMethyl
On mercaptan,
heating withCH Fehling’s reagent a red precipitate is formed.
3SH, is one of the substances responsible for bad breath and is often used
to impart a smell to natural gas in a pipeline.
C With 2,4-dinitrophenylhydrazine reagent an orange precipitate is formed.
DWhat will hydrogen
With be formedcyanide
when CHan3SH is burned
aldehyde in an excess of air?
is formed.
A CO CO2 H2 S
30 The
B ester
CO CH CH2 CH
H23 O SO23CO2 CH3 is responsible for the aroma of apples.
C CO
When this
2 ester
H2 O is SO
hydrolysed
2 by acid in the stomach, what is the empirical formula of the organic
acid produced?
D CO2 H2 O SO3
A CH4O B C2 H4 O C C 2 H 4 O2 D C 3 H 7 O2
18 A solid nitrate fertiliser reacts with an alkali to produce a gas which turns damp pH paper blue.

What is the empirical formula of this fertiliser?

A NO3 B NHO3 C NH2 O D N 2 H 4 O3

19 Glucose, C6 H12 O6 , is a product of photosynthesis.

It has the following structure.

H C O

H C OH

HO C H

H C OH

H C OH

H C OH

How many chiral centres does the molecule have?

© UCLES 2007 9701/01/O/N/07

A 1 B 2 C 4 D 6
23 [N’06 p11 q4] 4

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 and the total volume, V, of residual gas measured
again at room temperature and pressure.

Which graph represents the results that would be obtained?

A B
V / cm 3
V / cm 3

X
80 80
X
60 60
X
40 X 40
X X
20 X 20
X
0 0
CH4 C3 H 8 CH4 C3 H8
C 2H 6 C4H10 C 2H 6 C4H10

C D
V / cm 3
V / cm 3

80 80

60 60 X
X
X X
X
40 X 40
X
20 X 20

0 0
CH4 C3 H 8 CH4 C3 H8
C 2H 6 C4H10 C 2H 6 C4H10

© UCLES 2006 9701/01/O/N/06

24 [N’06 p11 q5] 5

5 Which diagram describes the formation of a π bond from the overlap of its orbitals?

D 8

15 Which of the following is not a correct statement about iodine?

A A crystal of iodine contains covalent bonds and van der Waals’ forces.

6 BFor Iodine vapour

an ideal is purple.
gas, the plot of pV against p is a straight line. For a real gas, such a plot shows a
Cdeviation from ideal behaviour.
energy ofThe plotsisof against
pV than forbromine.
thatpof three real gases are shown below.
25 [N’06 p11 q11]
The first ionisation iodine less7
DTheThe
gases represented
hydride are
of iodine is ammonia,
of greater hydrogen and nitrogen.
thermal stability than that of bromine.
11 The equilibrium constant, Kc, for the reaction to form ethyl ethanoate from ethanol and ethanoic
acid, C2H5OH + CH3CO2H CH3CO2C2H5 + H2O, at 60 oC is 4.00.
16 Mixing aqueous silver nitrate and aqueous sodium chloride produces a precipitate.
When 1.00 mol each of ethanol and ethanoic acid are allowed to reach equilibrium at 60 oC, what
Xa colourless solution?
is the number
Addition of moles
of which of ethyl
reagent to theethanoate formed?
mixture gives
Y Z
A aqueous
1 ammonia 2 1 3
A
3 pV 3
B C
4
D
ideal
4 gas
B aqueous potassium iodide
C dilute hydrochloric acid
12 The diagram shows the Maxwell-Boltzmann energy distribution curves for molecules of a sample
D a gas
dilute
at nitric acid
26 [N’06 p11 q17]
of two different temperatures.
0
Which letter on the axes p
0 represents the most probable energy of the molecules at the lower
17 temperature?
Which is the complete list of all the products from the reaction of concentrated sulphuric acid with
potassium bromide?
What are the identities of the gases X, Y and Z?

A
A potassium hydrogensulphate and hydrogen bromide
X Y Z
B potassium hydrogensulphate, hydrogen bromide and bromine
A ammonia nitrogen hydrogen
B hydrogen B
C potassium hydrogensulphate,
nitrogen
hydrogen bromide, bromine and water
ammonia
D potassium hydrogensulphate, hydrogen bromide, bromine, water and sulphur dioxide
C nitrogen ammonia hydrogen
D nitrogen hydrogen ammonia
18 Sulphur dioxide is an important food preservative.

Which property makes sulphur dioxide useful in this role?

A It is a gas.
© UCLES 2006 9701/01/O/N/06 [Turn over
B It is a reducing agent. C D
C It reacts with oxygen to form sulphur trioxide.
13 Steam is passed
D It reacts withover heated
water magnesium
to form to give compound X and hydrogen.
an acidic solution.

What is not a property of compound X?

A It has a high melting point.

 A potassium hydrogensulphate and hydrogen bromide
B potassium hydrogensulphate, hydrogen bromide and bromine
C potassium hydrogensulphate, hydrogen bromide, bromine and water
D potassium hydrogensulphate, hydrogen bromide, bromine, water and sulphur dioxide
27 [N’06 p11 q18]

18 Sulphur dioxide is an important food preservative.

4

8 Which
In property makes
the conversion sulphur dioxide
of compound useful in this
X into compound Z, role?
it was found that the reaction proceeded by
way of compound Y, which could be isolated. The following steps were involved.
A It is a gas.
B It is a reducing agent. X → Y ; ∆H, positive
Y → Z ; ∆H, negative
C It reacts with oxygen to form sulphur trioxide.
Which reaction profile fits these data?
D It reacts with water to form an acidic solution.
A B C D

Y
Y Y
energy

energy

energy

energy
28 [N’06 p11 q19] 9 Z X
X
X Z
X acid, sulphur dioxide is mixedY with air and
Z of sulphuric
Z
19 In the Contact process for the production
passed over a vanadium(V) oxide catalyst at about 450 o C and a pressure slightly above
progress pressure.
atmospheric of progress of progress of progress of
reaction reaction reaction reaction
2SO2 + O2 2SO3 ; ∆H negative

9 The nickel-cadmium
What rechargeable
affects the choice battery
of conditions is based
for this upon the following overall reaction.
reaction?

A Cd +would
A lower temperature 2NiOOH 4H2 O
not +raise →concentration
the Cd(OH)2 + 2Ni(OH)
of SO32 .H
at2 O
equilibrium.
© UCLES 2006 9701/01/O/N/06
o
B
WhatAtisathe
lower temperature
oxidation numberofof300 C the
nickel V2 Obeginning
at the 5 catalystand
would not end
at the be effective.
of the reaction?
C At 450 o C nitrogen and oxygen from the air combine to form nitrogen oxides which are
neededbeginning end
as additional catalysts.
D A The heat +1.5 +2
generated by the reaction raises the temperature of the catalyst bed to 600 o C at
B which temperature
+2 the reaction+3begins to take place.

C +3 +2
20 In which class of compound, in its general formula, is the ratio of hydrogen atoms to carbon
D the highest?
atoms +3 +4
29 [J’06 p11 q10]
A alcohols
10 At a total pressure of 1.0 atm, dinitrogen tetraoxide is 50 % dissociated at a temperature of 60 o C,
B aldehydes
according to the following equation.
C carboxylic acids N 2 O4 2NO2
D halogenoalkanes
What is the value of the equilibrium constant, Kp, for this reaction at 60 o C?

A 1 / atm B 2 / atm C 4 /3 atm D 2 atm

21 What 3 is the total number3 of different chloroethanes, formula C2 H6-nCln, where n can be any
integer from 1 to 4?

A 4 B 6 C 7 D 8

22 Which reaction is an example of nucleophilic substitution?

A CH3 CH2 Br → CH2 =CH2 + HBr

B CH2 =CH2 + HBr → CH3 CH2 Br

C C3 H7 Br + H2 O → C3 H7 OH + HBr

D C2 H6 + Br2 → C2 H5 Br + HBr
© UCLES 2006 9701/01/M/J/06
 14

SECTION
Section B
14 B
For each of the questions in this section, one or more of the three numbered statements 1 to 3 may
The
beresponses
correct. A to D should be selected on the basis of
Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against
A that you consider to be
the statements B correct). C D
1, 2 and
The responses 3 D should be selected
A to 1 and 2 on the 11
basis of 2 and 3 1 only
are only are only are is
Section B
correct
A correct
B Ccorrect D correct
For each of the questions in this section, one or more of the three numbered statements 1 to 3 may
be correct. 1, 2 and 3 1 and 2 2 and 3 1 only
No other combination
are of statements is used as a correct
only are only areresponse. is
Decide whethercorrect correctis or is not correct
each of the statements correct correctto put a tick against
(you may find it helpful
the statements that you consider to be correct).
38NoLimonene is foundofinstatements
other combination lemons. is used as a correct response.
21
The [N’09 p11Aq31]
responses to D should be selected on the basis of

31 A monomer B polymerisation. AC1 mol sample of theDmonomer is completely

A undergoes addition
polymerised.
1, 2 and 3 1 and 2 2 and 3 1 only
How many
are moles of polymer might,
only are theoretically,only
be formed?
are is
correct correct correct correct
1 1
2 10–6
No other combination of statements is used as a correct response.
3
1 limonene
6 .02 × 1023
31 Limonene
Kevlar hasistheheated with
structure concentrated acidified potassium manganate(VII).
below.

O physical properties
O are due to hydrogen O
bonding betweenOwater molecules?
Which compounds are produced?
32 Which
22 [N’09 p12 q35]
1 C Water C boiling
has a higher N point than N 15 C
H2 S. C N N
1 CH3COCH2CH2CH(CH2CO2H)2
2 Icestatements
floats on water.
about H
35 Which
2 correct?
CO2 H sodium bromide with concentrated
the reaction of solid H sulfuricHacid are
3 The H−O−H bond angle in water is approximately 104°.
3COCH
3Compared
1 CH 2CH2rope
CH(COCH
to a bromide
Hydrogen steel is of 3)CH
similar
a product COreaction.
of 2the 2H
dimensions, a Kevlar rope is both lighter and stronger.

33 Which
2Which properties
Sulfuric acid of
equilibria, which help
isinKevlar
oxidised to explain
alltospecies
sulfur are these
dioxide. facts?
gaseous, would have equilibrium constants, Kp, with no
39 Chlorofluoroalkanes
units?
13 TheBromide
fibresions are have
of Kevlar alignbeen
reduced used
to bromine.
due to as thebonding.
hydrogen refrigerant in refrigerators but care has to be taken in
disposing of old refrigerators.
1 sulfur dioxide and oxygen in equilibrium with sulfur trioxide
2 The mass per unit length is less in a Kevlar rope than in a steel rope.
36 Which
Which statements
2 hydrogen andare
statements about
iodine chlorofluoroalkanes
truein equilibrium
for are correct?
with hydrogen
an SN2 reaction? iodide
3 The Kevlar molecule has no permanent dipole.
23 [N’08
13 One p11
carbon q32]
monoxide and
as steam in bond
equilibrium with carbon dioxide and hydrogen
1 C–Cl bonds more readily undergo homolytic fission than C–F bonds.
bond is broken another is formed.
2 The
32 Which formation
of the of acan
following transition
act as astate involves the collision
Bronsted-Lowry acid? of two molecules or ions.
2 Care is taken in the disposal of old refrigerators because of possible ozone depletion.
13 HA3O
carbon
+ atom in the transition state is bonded, either fully or partially, to five other atoms.
3 C2H4Cl F is more volatile than C2H6.
+
2 NH 4
37 The chlorine free radical takes part in the destruction of the ozone layer.
40 The M
3 H2r Oof compound X is 72. The composition by mass of X is 66.7% carbon, 11.1% hydrogen
and 22.2%
Which oxygen.
statements aboutXthis
gives an orange
free radical precipitate with 2,4-dinitrophenylhydrazine reagent.
are correct?
X 1does isnot
It given reactbywith
formed the Fehling’s
heterolytic reagent.
fission
33 Under conditions, what governs theofrate
theofcovalent bond
a forward in a chlorine-containing molecule.
reaction?
© UCLES 2009 9701/11/O/N/09
What Itcan
12 the hasbe deduced
a single
activation from
unpaired
energy this information?
electron.
of the reaction
3 It has the same electron arrangement as a chlorine atom.
12 Xthe
is enthalpy
a carbonyl compound.
change of the reaction

23 Xthe
is equilibrium
a ketone. constant of the reaction
38 The diagram shows an experiment.
3 X is butanone.
silica, alumina
or baked clay
liquid
© UCLES 2008 X on 9701/01/O/N/08 [Turn over
mineral
© UCLES 2018 wool gas collected
9701/11/M/J/18
 1 H 3O+
+
2 NH 4

3 H 2O
24 [N’08 p11 q33]

33 Under given conditions, what governs the rate of a forward reaction?

1 the activation energy of the reaction 13

38 2Which
theofenthalpy change
the following of the
would be reaction
suitable for use in a fire extinguisher?
31 the
CBrFequilibrium constant of the reaction
3

2 CH3(CH2)5CH2Br
3 HCl
25© UCLES
[N’08 p11 q39]
2008 9701/01/O/N/08 [Turn over

39 During the bromination of methane, the free radical CH•3 is generated and a possible terminating
step of this reaction is the formation of C2H6 by the combination of two free radicals.

What could be produced in a terminating step during the bromination of propane?

11
CH3
1 CH3CH2CH2CHCH3 Section B
14
CHquestions
For each of the 3
in this section, one or more of the three numbered statements 1 to 3 may
The responses ACH
be correct. to3D should be selected on the basis of
2 whether
Decide CH3CHCHCH
each of3 the statements is or is not correct (you may find it helpful to put a tick against
the statementsAthat you consider to Bbe correct). C D
CH3
3 CH 1, 2CH
The responses3
A CHCH
and
2CH3
to3 D should be1selected
and 2 on the basis2 ofand 3 1 only
are2 only are only are is
correct correct correct correct
A B C D
40 The structure of the antioxidant vitamin C is shown in the diagram.
1, 2 and 3 of statements
No other combination 1 and
is 2 2 and
used as a correct 3
response. 1 only
26 [J’08 p11are q34] only HO
are OH only are is
correct correct C C correct correct
34 Water is added to anhydrous aluminium chloride to make a 0.1 mol dm-3 solution.
O C CHCH(OH)CH2OH
No other
Whichcombination
observations are correct?is used O
of statements as a correct response.

1On the
Thebasis
reaction
of thisis endothermic.
structure, which properties is vitamin C likely to have?
31 What are assumptions of the kinetic theory of gases and hence of the ideal gas equation,
21 =The
PV is solution
ItnRT ?
soluble iniswater.
acidic.
3 The solution contains the ion [Al(H2O)6]3+.
12 Molecules moveaqueous
It decolourises without bromine
interacting with one another except for collisions.
rapidly.
23 Intermolecular forcesreagent.
It reduces Fehling’s are negligible.
35 The electronic structure of the outer shell of the element radium is 7s2.
3 Intermolecular distances are much greater than the molecular size.
27 [N’07
Whichp11 q32] will be correct for radium within its group?
statements

32 1
Carbon
Themonoxide burns
element will readily inwater,
decompose oxygen to form carbon
liberating dioxide.
hydrogen.
2
WhatThe
canelement will show
be deduced from an
thisoxidation number of +2 in all its compounds.
information?
3
1 Radium has the highest
The +4 oxidation state offirst ionisation
carbon energy.
is more stable than the +2 state.
2 The standard enthalpy change of formation of carbon dioxide is more negative than that of
36 When the yellow
carbon liquid NCl3 is stirred into aqueous sodium hydroxide, the reaction that occurs
monoxide.
can be represented by the following equation.
3 The value of the equilibrium constant for the reaction, 2CO(g) + O2(g) 2CO2(g), is likely to
be high.2NCl3(l) + 6NaOH(aq) → N2(g) + 3NaCl (aq) + 3NaOCl (aq) + 3H2O(l)

What will be the result of this reaction?

© UCLES 2008 9701/01/O/N/08
1 The nitrogen is oxidised.
2 A bleaching solution remains after the reaction.
3 The final solution gives a precipitate with acidified silver nitrate.
 A B C D

1, 2 and 3 1 and 2 2 and 3 1 only

are only are only are is
correct correct correct correct

13
No other combination of statements is used as a correct response.
28 [N’07 p11 q33]
34 Two bulbs R and S, connected by a mercury manometer, are held in a thermostat, as shown. The
volume of R is twice that of S. R contains gas, X, at the same pressure as the nitrogen in S.
33 Phosphorus pentachloride is introduced into an empty gas syringe which has a movable, tightly-
fitting plunger. The gas is allowed to expand until equilibrium is reached at a temperature at
R
which the phosphorus pentachloride partially dissociates.
S
PCl5(g) PCl3(g) + Cl2(g)
X nitrogen
13 thermostat
self-sealing
35 When a fireworkcapisfor
lit a fuel and an oxidising agentmanometer
react.
introducing
gas plunger
sample
In such a firework, magnesium is the fuel and mercury
barium nitrate is the oxidising agent.

Which the
When solidtemperature
products are
is produced
increased,when thegases
which firework is lit?R would cause the mercury level in the
in bulb
syringe
right-hand limb of the manometer to rise? oven
1 BaO
1
2 an
MgOequilibrium mixture N2F4(g) 2NF2(g); ∆H positive
Which statements are correct?
2
3 an equilibrium
Mg(NO 3)2
mixture CH3NC(g) CH3CN(g); ∆H negative
1 The equilibrium pressure inside the syringe will be greater than atmospheric pressure.
3 nitrogen
2 When the plunger is pushed in the equilibrium adjusts to produce more PCl5(g).
36 Why is the addition of concentrated sulphuric acid to solid potassium iodide unsuitable for the
preparation
3 The volume of hydrogen
of gas iodide?
in the syringe at equilibrium will be greater than if no dissociation had
35 Which statements concerning the third period elements (sodium to argon) and their compounds
occurred.
are
1 correct?
Hydrogen iodide is not displaced by sulphuric acid.
1
2 TheIodideelements
ions arebecome
oxidisedmore electronegative from sodium to chlorine.
to iodine.
34 Which statements are correct about the activation energy of a reaction?
2
3 Aluminium
The productoxide is the only oxide
is contaminated which compounds.
by sulphur is insoluble in water.
29 [N’07
1 It isp11 q37]for the forward and back reactions in an exothermic process.
different
3 The maximum oxidation state is shown by silicon.
2 It is low for a reaction that takes place slowly.
37 Which mixtures, on heating, produce the gas ND3?
2
3 =It of
[D
36 Use is unaffected
, anData
1Hthe isotopebyofthe
Booklet ispresence
hydrogen] of this
relevant to a catalyst.
question.

1 CaO(s)
The elementand ND4Cl(s)
astatine lies below iodine in Group VII of the Periodic Table.
2 CH3CN and NaOD in D2O
What will be the properties of astatine?
3 NDH3Cl and NaOD in D2O
1 It forms diatomic molecules which dissociate more readily than chlorine molecules.
2 It reacts explosively with hydrogen.
38 Which structures show a primary alcohol that cannot be dehydrated to form an alkene?
3 It is a good reducing agent.
30 [J’07
1 CH p11
3OHq37]
2 CH CH2OH
37 Nitrogen3 and oxygen react in a hot car engine to form nitrogen monoxide which is a serious
pollutant
3 2007
© UCLES
in our
CH3CH(OH)CH cities3 and in the countryside. However, nitrogen and oxygen do not react at room
9701/01/O/N/07
temperature.

39 Which statements
In the reaction help toan
between explain why and
aldehyde nitrogen
HCNand oxygenby
catalysed doNaCN,
not react at room
which temperature?
statements about the
reaction mechanism are true?
1 The reaction is endothermic.
1
2 A high
A new carbon-carbon bond
activation energy is formed.
is required.
2
3 In the intermediate,
Nitrogen has a high the
bondoxygen carries a negative charge.
energy.
3 The last stage involves the formation of a hydrogen-oxygen bond.
© UCLES 2007 9701/01/M/J/07 [Turn over
 15
1 There is a total of two chiral centres present in the menthol molecule.
37 The On
2 following three
reaction withhydrocarbons
concentratedall occur naturally.
sulphuric acid, menthol produces a mixture of two alkenes.
Which
3 of theseofwill
A solution be splitpotassium
acidified into two organic 15
compounds,
dichromate(VI), both containing
on warming a ketone
with menthol, group, colour
changes when
treated
fromwith hot acidified
orange to green.potassium manganate(VII)?
31
37 [J’07 p11 q40]
The following three hydrocarbons all occur naturally.

Which
40 Fats andof grease
these will
thatbe splitupinto
build on two
pansorganic
used incompounds,
cooking areboth containing
esters. a ketone
Pans which group,
are dirty fromwhen
fats
1
treated
or with
grease mayhot
be 2
acidified
cleaned potassium
by heating 3
manganate(VII)?
them with a reagent that will react with the ester group.

What may be used to clean such pans by this reaction?

11 2 ethanoic acid, CH33CO2H

vinegar - aqueous

38 2 alcohol
Which - ethanol,ofC2fluoroalkanes?
are properties H5OH
3 baking powder - sodium hydrogencarbonate, NaHCO3
1 They are less reactive than the corresponding chloroalkanes.

38 2Which
They
areare non-flammable.
properties of fluoroalkanes?
© UCLES
3 2007
The C-F bond is stronger than a C-Cl9701/01/M/J/07
bond.
32 [N’06 p11are
1 They q39]
less reactive than the corresponding chloroalkanes.
2 They are non-flammable.
39 Which compounds are able to react with concentrated sulphuric acid to give a product that will
3 The C-Facidic
decolourise bondpotassium
is strongermanganate(VII)?
than a C-Cl bond.

1 (CH3)3COH
39 Which compounds are able to react with concentrated sulphuric acid to give a product that will
CH3CH2CH(OH)CH
2decolourise 3
acidic potassium manganate(VII)?
3 CH3CO2H
1 (CH3)3COH
2 CH3CH2CH(OH)CH3
40 Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group.
3 CH3CO2H
33 [N’06 p11 q40] R

40 Rofecoxib, an efficient drug against arthritis, has the following structure. R is an inert group.

CH2 R
C
O
* CH2 C
C
C
O O
* C
C
Which reactions are possible with this structure?
O
1 The bond marked is hydrolysed by heating with aqueous sodium hydroxide.
2Which
Aqueous bromine
reactions is decolourised.
are possible with this structure?
3 An orange precipitate is formed with 2,4-dinitrophenylhydrazine reagent.
1 The bond marked is hydrolysed by heating with aqueous sodium hydroxide.
2 Aqueous bromine is decolourised.
3 An orange precipitate is formed with 2,4-dinitrophenylhydrazine reagent.

© UCLES 2006 9701/01/O/N/06

© UCLES 2006 9701/01/O/N/06

 1, 2 and 3 1 and 2 2 and 3 1 only
are only are only are is
correct correct correct correct

No other combination of statements is used as a correct response.

34 [J’06 p11 q33]

33 Hydrazine, N2H4, is widely used as a rocket fuel because it reacts with oxygen as shown,
producing ‘environmentally friendly’ gases.

N2H4(l) + O2(g) → N2(g) + 2H2O(g) ∆H = –534 kJ mol–1

14
Despite its use as a rocket fuel, hydrazine does not spontaneously burn in oxygen.
The responses A to D should be selected on the basis of
Why does hydrazine not burn spontaneously?

1 The activation
A energy is too high.
B C D
2 The1,N≡N
2 andbond
3 is very strong.
1 and 2 2 and 3 1 only
are
3 Hydrazine is a liquid. only are only are is
correct correct correct correct

34 Compound
No other X
combination of statements is used as a correct response.
35 [J’06 p11 q38]
• does not conduct electricity when in a liquid state,
38 Deuterium, D, is the 21H isotope of hydrogen. DBr has the same chemical properties as HBr.
• when added to water produces a solution that readily conducts electricity.

Whichcould
What compounds
X be? could be made by the reaction of DBr with another compound in a single
reaction?
1 MgCl2
Br
2 SiCl4 D
1
3 PCl3

2 CHBr2CHDBr

OD
3 CH3CH
Br

39 How can the rate of reaction between ethanal and aqueous hydrogen cyanide be increased?

1 by irradiation with ultraviolet light

© UCLES
2 2006
by a rise in temperature 9701/01/M/J/06

3 by the addition of a small quantity of aqueous sodium cyanide

40 Which statements about lactic acid, CH3CH(OH)CO2H, are correct?

1 Lactic acid forms optical isomers.

2 Two hydrogen atoms per lactic acid molecule can be involved in hydrogen bonding.
3 Lactic acid would form an aldehyde when oxidised by acidified potassium dichromate(VI).

© UCLES 2006 9701/01/M/J/06