Halogenoalkanes Answers

C CH3CO2H + CH3CH2CHCH2OH
CH3
D CH3CO2H + CH3CHCH2CH2OH
HALOGENOALKANES WS 1
CH3
SECTION A
1 The hydrolysis of 1-chloropropane to produce propan-1-ol is much slower than the corresponding
23
hydrolysis of 1-iodopropane. 11
Whichmany
29 How statement explains
geometrical this observation?
(cis-trans) isomers are there of hex-2,4-diene, CH3CH=CHCH=CHCH3?
Chlorine is more electronegative 8
thangeometric
iodine.
A none; hex-2,4-diene does not show isomerism
19 B The
Use 2 bond
of the strength
Data of is
Booklet C – I bond
therelevant is less
to this than that of the C – Cl bond.
question.
C The
3
In an carbon atom0.125
experiment, in themol
C – of
Cl chlorine
bond is more
gas,δ+Clthan that in the C – I bond.
2, is reacted with an excess of cold aqueous
sodium
Thehydroxide. One of the products isaddition
a compound of sodium, oxygen, and chlorine.

D
D 4 hydrolysis involves a nucleophilic reaction.
Which mass of this product is formed? [S'14 P11 Q23]
2 Butanoic
30 A 9.31 g acid can beBproduced
13.3 g from 1-bromopropane
C 18.6 g using reagents
D 26.6Xgand Y as shown below.
reagent X reagent Y
20 The diagram shows the skeletal formula ofcompound
1-bromopropane 9 Q
phenazine. butanoic acid
© UCLES 2014 9701/11/M/J/14 [Turn over
23 What N heated with an aqueous solution of sodium
couldofbestructural
An ester reagents formula
X and Y?CH3CO2CH3 is
hydroxide.
X Y
N
What are the two organic products of this reaction?
A KCN in ethanol HCl (aq)
A ethanoic acid and methanol
B KCN in ethanol phenazine
NaOH(aq)
B methanoic acid and ethanol
C is the
What NH 3 in ethanol
empirical HCl (aq)
formula of phenazine?
C sodium ethanoate and methanol
+ 2–
A D C6H4N NaOH(aq) B C6H6N H / Cr2OC 7 (aq)
C12H8N2 D C12H12N2
D sodium methanoate and ethanol

[S'17 P13 Q29]
3 Halogenoalkanes
21
24 Ethene reacts withundergo
aqueousabromine
range of
tonucleophilic substitution
give two products, CH2BrCHreactions.
2Br and CH2BrCH2OH.
Which
Which reaction
statementproceeds
about these by an SisN1correct?
onlyproducts mechanism?
A
A CH 3CH
Both 2Br + are
products NH3obtained in this reaction by electrophilic substitution.
–
B
B CH 3CH
Both 2CH2I are
products + OH
obtained in this reaction by nucleophilic addition.
C
C CH 3CHBrCH
Both + NH
products3 can be 3hydrolysed to form the same organic compound.
D Both3)products – form hydrogen bonds with water.

can
D (CH 3CI + OH
[S'14 P12 Q21]
4 Which
25
22 Which alcohol
statement does
has not correctly
a chiral describe
centre and can bea problem
oxidisedrelated to the disposal of PVC?
to a ketone?
A
A PVC is slowly degraded in the environment by bacteria and fungi.
pentan-2-ol
B
B PVC is slowly degraded in the environment by sunlight.
pentan-3-ol
C When PVC is burnt, a significant amount of ethene gas is present in the products.
C 3-methylhexan-1-ol
D
D
When PVC is burnt, a significant amount of HCl gas is present in the products.
3-methylhexan-3-ol
[S'14 P12 Q25]
26 Compound X, C4H8O, produces an orange precipitate when it is reacted with

2,4-dinitrophenylhydrazine reagent. Compound X produces a carboxylic acid when heated under
reflux with an acidified solution of potassium dichromate(VI).
What could be compound X?
A butanal
B butanone
© UCLES
C 2014 9701/11/M/J/14 [Turn over
CEDAR COLLEGE 261 HALOGENOALKANES WS 1
2-methylbutanal
D 4-hydroxybut-1-ene
© UCLES 2014 9701/12/M/J/14

109
5 Dichlorodifluoromethane,
24
27 Coniine is the major constituent
CCl 2F2of the been
, has poison ‘oil of
used hemlock’.
in aerosol propellants and as a refrigerant.
Which statement helps to explain why dichlorodifluoromethane is chemically inert?
A All fluorine compounds are non-flammable.

N CH2CH2CH3
B Fluorine is highly electronegative.
H
C The carbon-fluorine bond energy is large.
coniine
D The carbon-fluorine bond has a low polarity.
9 [S'14 P12 Q27]

Coniine can be synthesised by reacting ammonia with a dibromo compound, X.
6 The
23
28 A compound Y, C4Hthe
diagram shows 9Br,structure
undergoes hydrolysis inacid.
of ethanedioic aqueous alkali to form an alcohol, C4H9OH. The
NH + C8H16Br2 → coniine + 2HBr
rate of this reaction is found to3 be unaffected by changes in the concentration of OH– ions
present. HO
X OH
Whichisisthe
What thename
most of
likely X?structureCof Y?C
molecular
compound
A CH3CH2CH2CH2Br
1,1-dibromo-2-propylcyclopentane O O
B CH3CH2acid
Ethanedioic CHBrCH
B 1,2-dibromo-2-propylcyclopentane
reacts
3 with ethanol in the presence of a few drops of concentrated sulfuric acid
to form a diester. The molecular formula of the diester is C6H10O4.
C (CH3)2CHCH2Br
C 1,4-dibromooctane
What is the structural formula of the diester?
DD 1,5-dibromooctane
(CH 3)3CBr

A CH3CH2CO2CO2CH2CH3 [W'14 P13 Q23]
7 B
24
25 Compound
CH3CH2XOCOCO
canreacts
2-bromopropane be made fromhot
2CHwith
2CHa3
2-hydroxybutanoic acid. of sodium hydroxide in ethanol.
concentrated solution
C CHsubstance
Which 3CH2O2COis 2CCH CH3 product of thisOreaction?
the 2major
H
D CH 3CO2CH2CH2OCOCH3 C
A propan-1-ol
C O
CH3 CH2
B propan-2-ol CH2 CH3
29 When heated with KOH dissolved in O ethanol,Chalogenoalkanes can undergo an elimination
C
H
C 2-hydroxypropene
reaction to form alkenes.
O
are the possible elimination products when 2-bromobutane is heated with KOH dissolved in
D propene
What
compound X
9 [S'15 P11 Q25]
ethanol?
8 A
24
26 Coniine
The
WhatCH is the major
presence
3CH=CHCH
should
constituent
of a 3halogen
be heatedonly of the
in an poison
organic ‘oil of hemlock’.
compound may be detected by warming the organic
with 2-hydroxybutanoic acid in order to make compound X?
compound with aqueous silver nitrate.
B CH3CH2CH=CH2 only
A acidified potassium dichromate(VI)
Which compound would be the quickest to produce a precipitate?
C CH3CH=CHCH3 and CH3CH2CH=CH2
B aluminium oxide
A B N CH2CH
C 2CH3 D
D CH3CH=CHCH 3 and CH2=CHCH=CH2
C concentrated sulfuric acid
Cl F H F Cl
D dilute sodium hydroxide
coniine
Cl Cl F Br
Coniine
25 The can be synthesised
compound by reacting ammonia
known as ‘gamma-linolenic with
acid’ is a dibromo
found in the compound,
seeds of theX.evening primrose
I
plant.
Cl NH3 + C8HF F
16Br2 → coniine + 2HBr
CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H
X
gamma-linolenic acid
What is the name of compound X?
How many cis-trans isomers are there with this structural formula?
A 1,1-dibromo-2-propylcyclopentane
A 3 B 6 C 8 D 12
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B 2014
1,2-dibromo-2-propylcyclopentane 9701/12/M/J/14
C 1,4-dibromooctane
D 1,5-dibromooctane
[S'15 P11 Q24]
25 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol.
Which substance is the major product of this reaction?

CEDAR
A COLLEGE
propan-1-ol 262 HALOGENOALKANES WS 1
© UCLES 2014 9701/13/O/N/14 [Turn over
B propan-2-ol
C 2-hydroxypropene
D propene
99
9 The
26 presence of a halogen in an organic compound may be detected by warming the organic
Four students,
students, W,
22 compound
Four W, X,
X, Y
Y and
and Z,
Z, made
made thethe following
following statements
statements about
about alkanes
alkanes and
and alkenes.
alkenes.
with aqueous silver nitrate.
W ‘Bromine
W ‘Bromine
Which compound reacts
wouldreacts with
be thewith alkanes
alkanes
quickest by electrophilic
by electrophilic
to produce substitution.’
substitution.’
a precipitate?
X
X ‘Bromine reacts
‘Bromine reacts with
with alkenes
alkenes by
by aa free-radical
free-radical addition
addition mechanism.’
mechanism.’
A B C D
Y
Y Cl
‘Alkenes
‘Alkenes can
can be
be oxidised
oxidised Fby
by acidified
acidified manganate(
manganate( FVII
VII )
) ions.’
ions.’ Cl
Z
Z ‘Alkenes are
‘Alkenes are formed
formed from
from alkanes
alkanes by
by cracking.’
cracking.’
Cltwo
Which
Which two students
students are Cl
are correct?
correct? F Br
A
A W
W and
and X
X Cl B
B W
W and
and ZZ FC
C X
X and
and Y
Y DI Y
D Y and
and ZZ F
[S'15 P11 Q26]
10
23 Butanedioic
Butanedioic acid
acid may
may be
be synthesised
synthesised in
in two
two steps
steps from
from 1,2-dibromoethane.
1,2-dibromoethane.
step
step 11 step
step 22
BrCH
BrCH22CH
CH22Br
Br X
X HO
HO22CCH
CCH22CH
CH22CO
CO22H
H
© UCLES 2015 reagents

Which
Which reagents could
could be
be used
used for
for this 9701/11/M/J/15
this synthesis?
synthesis? [Turn over
step
step 11 step
step 22
A
A HCN(g)
HCN(g) HCl
HCl(aq)
(aq)
B
B HCO
HCO22Na(aq)
Na(aq) HCl
HCl(aq)
(aq)
C
C KCN(alcoholic)
KCN(alcoholic) H
H22SO
SO44(aq)
(aq)
D
D NaOH(aq)
NaOH(aq) K
K22Cr
Cr22O
O77//H
H22SO
SO944(aq)
(aq)
[S'15 P12 Q23]
21 The diagram shows a molecule that has σ bonds and π bonds.
11
24 Which
Which reaction
reaction would
would not
not give
give propene?
propene?
O
A
A adding
adding excess
excess hot
hot concentrated
concentrated sulfuric
sulfuric acid
acid toto propan-1-ol
propan-1-ol
B adding CH 2 CH CH 2 C O CH 2 CH CH2
B adding warm
warm aqueous
aqueous sodium
sodium hydroxide
hydroxide to
to 2-bromopropane
2-bromopropane
C
C adding
How many σwarm
adding bondsethanolic
warm ethanolic sodium
sodium
are present hydroxide
hydroxide
in this to
molecule?to 1-bromopropane
1-bromopropane
D passing
passing propan-2-ol vapour
vapour over
over heated aluminium oxide

D 15
A propan-2-ol
B 17 heated
C 18aluminium oxideD 21
[S'15 P12 Q24]
12
22 The Finkelstein reaction occurs when NaI in propanone reacts with a chloroalkane or
bromoalkane. The halogen is directly replaced by I and the reaction only works for primary
halogenoalkanes.
Which halogenoalkane would produce compound X?
compound X
A (CH3)2CHCH(CH3)CH2CH2Br
B (CH3)2CHCH(CH3)CH2Br
C (CH3)2CHCH2CH2CH(CH3)Cl
© UCLES
D 2015
(CH3)2CHCH2CH(CH3)CH2Cl 9701/12/M/J/15 [Turn
[Turn over
© UCLES 2015 9701/12/M/J/15

over
[S'15 P13 Q22]
23 An ester P with a fruity odour has the following structural formula.
CH3 C
CEDAR COLLEGE OCH2 CH263

2 CH(CH3 )2 HALOGENOALKANES WS 1
Which compounds are produced when P is hydrolysed using hydrochloric acid?

C butan-2,3-diol
D 2-methylbutan-2-ol
13
25 A student prepares pentan-1-ol by the alkaline hydrolysis of 1-iodopentane. She gently warms the
reaction mixture for 20 minutes.
CH3CH2CH2CH2CH2I + OH– → CH3CH2CH2CH2CH2OH + I–
When the student uses 1-chloropentane to prepare the same alcohol she has to change the
condition of the reaction.
Which change in condition should she use and what is the correct reason for its use?
change in condition reason
A heat under reflux C–Cl bond is more polar than the C–I bond
B heat under reflux C–Cl bond is stronger than the C–I bond
C room temperature C–Cl bond is more polar than the C–I bond
D room temperature C–Cl bond is shorter than the C–I bond

12 [S'16 P11 Q25]
28 A tertiary bromoalkane, indicated here by C– Br , reacts with aqueous NaOH. The mechanism
14
has the reaction pathway below.
© UCLES 2016 9701/11/M/J/16
Y
energy C– Br + OH–
C– OH + Br –
extent of reaction
Which point in the diagram is correctly identified?
A X is C+
–
B X is HO C Br
C Y is C+
–
D Y is HO C Br
[S'15 P13 Q28]

29 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three
test-tubes containing 1.0 cm3 of aqueous silver nitrate at 60 °C.
In each case, a hydrolysis reaction occurred. R represents the butane chain C4H9 and X the
halogen atom.
H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq)
The rate of formation of cloudiness in the test-tubes was in the order RCl < RBr < RI.
Why is this?
CEDAR
A COLLEGE 264
The bond energy of R–X decreases from RCl to RI. HALOGENOALKANES WS 1
B The first ionisation energy of the halogen decreases from Cl to I.
D Y is HO C Br
15
29 Four drops of 1-chlorobutane, 1-bromobutane and 1-iodobutane were put separately into three
3
test-tubes containing 1.0 cm of aqueous silver nitrate at 60 °C.
In each case, a hydrolysis reaction occurred. R represents the butane chain C4H9 and X the
halogen atom.
The rate of formation of cloudiness in the test-tubes was in the order RCl < RBr < RI.
Why is this?
A The bond energy of R–X decreases from RCl to RI.
B The first ionisation energy of the halogen decreases from Cl to I.
C The solubility of AgX(s) decreases from AgCl to AgI.
D The R–X bond polarity decreases from RCl to RI.
99 [S'15 P13 Q29]
16
24
24 Which
Whichcompound
compoundundergoes
undergoesan
anSSNN11substitution
substitutionreaction
reactionwith
withNaOH(aq)?
NaOH(aq)?
AA CH CH CH
© UCLES 2015 3 3
CH2 2CH
CH2 2Br
Br 9701/13/M/J/15
BB (CH
(CH3 3))3 3CCH
CCH2 2II
CH3 3 Cl
CH Cl 9
23 CCompound
C Q can be made from propanone.
DD CH2 2=CHCl
CH =CHCl
[W'15 P13 Q24]

Q
17
25
25 If
If the
the starting
starting material
material isisiodoethane,
iodoethane, which
whichsequence
sequenceofofreactions
reactionswill
willproduce
producepropanoic
propanoicacid
acidasas
the
themain
Which main final
finalofproduct
types product ininwill
reaction goodQ yield?
good yield?
undergo?
A
A add
A addNaOH(aq),
NaOH(aq),
nucleophilic isolate
isolate
addition the
andtheorganic
organicproduct,
product,
electrophilic add
addition acidifiedKK2Cr
addacidified 2Cr2O
2O7 7and
andboil
boilunder
underreflux
reflux
B
B add
B addNaOH(aq),
NaOH(aq),
nucleophilic isolate
isolate
addition the
andtheorganic
organicproduct,
product,
nucleophilic addHH2SO
add
substitution 2SO4(aq)
4(aq)and
andboil
boilunder
underreflux
reflux
C
C heat
C heatwith
withHCN
nucleophilic
HCN ininethanol,
addition only isolate
ethanol, isolatethe
theorganic
organicproduct, addHH2SO
product,add 2SO4(aq) and boil under reflux
4(aq) and boil under reflux
D
D heat
D heatwith
withKCN
nucleophilic
KCN ininethanol,
substitution isolate
and
ethanol, the
theorganic
electrophilic
isolate product,
addition
organic addHH2SO
product,add 2SO4(aq) and boil under reflux
4(aq) and boil under reflux
[W'15 P13 Q25]
18
26
26 Which
24 The compound
depletion
Which cannot
of the
compound ozonebe
cannot oxidised
layer
be in the by
oxidised byacidified
upper potassium
atmosphere
acidified dichromate(
reduces
potassium VIVI) )solution
the Earth’s
dichromate( natural but
butdoes
solutionprotection
does
react
from with
withsodium
reactharmful metal?
ultraviolet
sodium metal?radiation.
A
A (CH
Which 33))33COH
compound
(CH COH would cause the most depletion of the ozone layer?
B CH33COCH
B CH 22CH
3COCH CH33B

A CCl F CF4 C CO2 D SO2

CH33CH
CC CH CH22CH
CH22CH
CH22OH
OH [W'15 P12 Q24]
CH33CH
DD CH CH22CH(OH)CH
CH(OH)CH33
27
27 Butan-2-ol
Butan-2-olcan
canbe
bemade
madeby
byreducing withHH2 2/ /Ni.
reducingXXwith Ni.
Butan-2-ol
Butan-2-olcan
canbe
bedehydrated
dehydratedtotoform
formYYand
andZZwhich
whichare
arestructural
structuralisomers
isomersofofeach
eachother.
other.
Which
Whichrow
rowisiscorrect?
correct?
cis-transisomerism
cis-trans isomerism
XXisis
isisshown
shownbyby
AA an
analdehyde
aldehyde both
bothYYand
andZZ
CEDAR B
COLLEGE 265 HALOGENOALKANES WS 1
B an
analdehyde
aldehyde only
onlyone
oneofofYYand
andZZ
CC aaketone
ketone both
bothYYand
andZZ
DD aaketone
ketone only
onlyone
oneofofYYand
andZZ
extent of reaction
10
The four reactions that follow are all exothermic.
19
25 Which
Structural isomerism
reaction wouldand stereoisomerism
not should
10 be considered in answering this question.
have such a pathway?
ACompound
CH3I +J NaCN
is reacted
→ with
isKOH
CH3CN +dissolved
NaI in ethanol. Three isomeric alkenes with molecular
25 A reaction pathway diagram shown.
formula C4H8 are formed.
What is J? CH3 CH3

B + 2NH3 → + NH4Br
A CH3 CH2Br CH2 CH
energy
2 Br NH2
B CH3 CH CH2 CH3

C + HBr → Br
Br extent of reaction
The four reactions that follow are all exothermic.

C CH3 CH CH2 Br conc. H2SO4 OH
D CH3 not
+ Hhave
2O such
Which reaction would heat
a pathway?
CH3 CH3
A CH3I + NaCN → CH3CN + NaI
CH3
26 Which volume CHof oxygen,
3 CH3 and pressure, is needed for complete combustion
at room temperature
BD 1.0CH
of mol
3 C
of Br + 2NH →
methylpropan-1-ol?
3 + NH4Br
Br NH2
108 dm3CH3 144 dm3 156 dm3 288 dm3

A B C D
[M'16 P12 Q25]
C + HBr → Br
2726 An
20 Which row correctly
unknown organic shows a primary,
compound a secondary
reacts and atotertiary
with sodium give aalcohol?
combustible gas as one product but
does not give a yellow precipitate with alkaline aqueous iodine.
primary secondary
conc. H SO OH tertiary
2 4
D
What CH3identity
is a possible + H2O of the unknown organic compound?
heat
CH2OH CH2OH CH3 CH2OH
A propanal
A CH2 CHOH CHOH
B propan-1-ol
CH3 CH3 CH2OH
26 Which volume of oxygen, at room temperature and pressure, is needed for complete combustion
of 1.0
C mol of methylpropan-1-ol?
propan-2-ol
A
D 108 dm3 CH2OH
propanone B 144 dm3 CH3 C 156 dm3 CH
D 3 288 dm3
B CH3 C H CH3 C OH CH3 C H [S'16 P13 Q28]
21 CH3 CH3 CH2OH

27 An unknown organic compound reacts with sodium to give a combustible gas as one product but
does not give a yellow precipitate with alkaline aqueous iodine.
CH2OH
What is a possible CH2OHorganic compound?
identity of the unknown CH2OH
A C propanal
CH3 C H CH3 C CH2OH CH3 C CH2OH
B propan-1-olH H CH2OH
© UCLES 2016 9701/13/M/J/16
C propan-2-olH CH3 CH3
D
D CH3 C
propanone
OH CH3 C OH 10 CH3 C OH
[S'16 P13 Q27]

H 3 H CH
22 The reaction CH3CH2CH2CH2Br + OH– → CH3CH2CH2CH2OH
22 + Br– proceeds via an SN2
mechanism.
The reaction (CH3)3CBr + OH– → (CH3)3COH + Br– proceeds via an SN1 mechanism.
© UCLES 2016 9701/12/F/M/16
Which statement about these two reactions is correct?
A Both reactions involve homolytic bond fission.

© UCLES 2016 9701/13/M/J/16
B Both reactions involve hydroxide ions acting as electron pair donors.
C Both reactions involve the formation of a positively-charged intermediate.
D Both reactions occur in a single step.
[W'16 P12 Q22]
23 The equation shows a reaction that occurs between carbon monoxide and nitrogen monoxide in a
CEDAR COLLEGE
catalytic converter. 266 HALOGENOALKANES WS 1
2CO(g) + 2NO(g) → 2CO2(g) + N2(g)

R
Which statement is correct? R
A They are chain isomers of each other. OH
B They are geometrical isomers of each other.

24 Chloroethane can be used to make sodium propanoate.
23
C They are optical isomers of each other.
D chloroethane
They are positional isomers Q10
of each other. sodium propanoate
24 The intermediate,
A sample Q, ofis ethanol
of 2.76 g hydrolysed
was with boiling
mixed with aqueous
an excesssodium hydroxide
of aqueous to give
acidified sodium
potassium
propanoate.
22 Which
dichromate( VI). The
equation represents
reactionthe initiation
mixture wasstep
thenofboiled
the substitution reaction
under reflux for onebetween
hour. Themethane and
required
chlorine?
organic product was then collected by distillation.8
Which reagent would produce the intermediate, Q, from chloroethane?
A CH CH3•ammonia
The concentrated
yield
4 of product +was
H• 75.0%.
22 A
Which compound wouldsolution
produce two different carboxylic acids when treated with hot,
acid was collected?VII) ions?
– +
concentrated,
B CH
Which
B mass
dilute
4 CHacidified
+
of product
sulfuric
3 H manganate(
C
C
A Cl 2 gA 2Cl
hydrogen
1.26 • B in 1.98
cyanide waterg B C 2.07 g CD 2.70 g D
+ –
D Cl 2 Cl cyanide
potassium + Cl in ethanol
25 Compound X is a single, pure, optical isomer. X is heated with an excess of concentrated H2[W'16
SO4.P11 Q24]
Only one organic product is formed.
23 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol.
24
What could X be?
What should be included in a diagram of the first step in the mechanism?
23 A Which A of bond are broken
types B C D of alkenes?
a curly
© UCLES 2016
arrow from a lone pair and formed
on the in the
OH– ion addition
to the
9701/13/O/N/16
polymerisation
C + atom of 1-bromopropane
OH
arrowoffrom the C +type
B a curly type atom
ofof 1-bromopropane to the
–
OH OH ion
HO CH2OH
bond
C a curly broken
arrow from thebond
C–Br formed
bond to the C atom
π only fission of the
D A the homolytic σ C–Br
only bond
[S'17 P12 Q23]

B π only σ and π
26 2-bromo-2-methylpropane undergoes nucleophilic substitution when heated under reflux with an
25 C σ and π σ only
aqueous solution of sodium hydroxide.
D σ and π σ and π
Which row is correct?
mechanism for (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO4. The product
24 2,3-dimethylpent-2-ene, reason
this reaction
of this reaction is treated with an excess of concentrated H2SO4 at 180 °C, giving a mixture of
isomeric
A hydrocarbons
SN1 withthe
molecular formula
hydroxide C7H12.in its approach to
ion is helped
the central carbon atom by the methyl groups
What
© UCLES 2017is the name of one of the isomeric9701/12/M/J/17
hydrocarbons? [Turn over
B SN1 the intermediate carbocation is stabilised
A by the inductive effect of the methyl groups
2,3-dimethylpenta-1,2-diene
SN2 the hydroxide ion is hindered in its approach to
B C cis-2,3-dimethylpenta-1,3-diene
the central carbon atom by the methyl groups
C 2,3-dimethylpenta-1,4-diene
D SN2 the intermediate carbocation is destabilised
D by the inductive effect of the methyl groups
3,4-dimethylpenta-1,3-diene

[S'17 P12 Q26]
25 Equal volumes of aqueous silver nitrate were added to separate small volumes of bromoethane
26
and iodoethane in two test-tubes. The test-tubes were shaken.
Which row about the observations made for bromoethane is correct?
colour of precipitate rate of reaction
A cream faster than for iodoethane

B cream slower than for iodoethane
C yellow faster than for iodoethane
© UCLES 2017 9701/12/M/J/17
D yellow slower than for iodoethane

[W'17 P12 Q25]
© UCLES 2017 9701/12/O/N/17

C CH3CHCHCl
● can be dehydrated to form two alkenes only.
D CHCl CHCH2CH2Cl
What could be the identity of compound X?
A CHorganic
24 Which 3CH2CH(CH3)CH2OH
reaction is an example of nucleophilic substitution?
27
B CH3CH2CH(OH)CH2CH3
A CH3CH2Br + NaOH → CH2CH2 + H2O + NaBr
C (CH3)2CHCH(OH)CH3
B CH3CH2Br + NaOH → CH3CH2OH + NaBr
D CH3CH2CH2CH(OH)CH3 7
C CH2CH2 + HCl → C2H5Cl
20 Fructose is a sugar with more than one chiral centre. The fructose molecule is shown with X, Y
D C2H6 + Cl 2 → C2H5Cl + HCl
25 Which volume of
and Z indicating hydrogen,
three measured under
carbon atoms. 7 room conditions, is produced when 0.160 g of
methanol reacts with an excess of sodium? [W'17 P13 Q24]
21 Citric
28
25 An organic
acid ion containing a carbon a OH
atom withacidnegative charge is called a carbanion.
A 60 cm3can be converted
B 120intocm3tricarballylic
C 240 cm in two
3 stages.
D An intermediate,
480 cm3 Q, is formed.
An organic ion containing a carbon H aC
atom with H charge is called a carbocation.
positive
CH CO
2 H 2 CH CO H 2 2
26 Compound X produces stage

X 1 hydroxide
a carboxylic Ostage
acidC when 2
The reaction
HO between
C CO aqueous
H sodium Q and heated under reflux
1-bromobutane
CH COproceeds
H
withby acidified
an SN2
potassium
mechanism. dichromate(VI). Compound X does not react with sodium metal.
2 2
HO C H
CH2 CO2H CH2 CO2H
What
What could
is the be
firstthe identity
step in theof compound X?
mechanism?
H C OH
citric acid tricarballylic acid
A propanal
A attack by a nucleophile on a carbon atom with a partial positive charge
Y H C OH
Which
B reagents
propanone are needed for each stage?
B heterolytic bond fission followed by attack by an electrophile on a carbanion
H C H
C
C propan-1-ol
heterolyticstage
bond1fission followed bystage attack2 by a nucleophile on a carbocation
Z OH
D propan-2-ol
A homolytic bond fission
concentrated H2SO4followed H by(g)
2
attack
and byNi a nucleophile on a carbocation
fructose [M'18 P12 Q21]

B concentrated H2SO4 LiAl H4
27
22 A
29 reactionX occurs
Compound can when a into
be converted sample
compoundof 1-chloropropane
Y in a single step. is heated under reflux with
Which
C carbon atoms are
LiAldissolved
H4 chiral centres?
H2SO4(aq)
sodium hydroxide in ethanol.
A D X, Y andNaOH(aq)
Z B X and Y only
H2(g)CandXNionly D Y only
Which row is correct? OH
X
typeofofalcohols
21 Which pair reactionare isomers
name ofofproduct
each other?
O O
A A butan-1-ol
elimination propan-1-ol
and 2,2-dimethylpropan-1-ol Y
B B butan-2-ol
What couldelimination
andidentity
be the of X? propene
2-methylpropan-2-ol
C C pentan-1-ol
substitution propan-1-ol
and 2-methylpropan-2-ol
A B C D
D D propan-2-ol
substitution propene
and 2-methylpropan-2-ol
[M'18 P12 Q27]

22 Sodium methoxide, Na+CH3O–, reacts with 2-chloro-2-methylpropane in a nucleophilic
30 –
substitution reaction. The nucleophile is the CH3O ion.
&
Which row is correct? c
© UCLES 2018 9701/12/F/M/18
23 Which compound reacts with
intermediate or 2,4-dinitrophenylhydrazine reagent but does not react with Tollens’
reagent? product C
transition state c
-
A A CH3COCO2H
(CH3)3C+ (CH3)3COCH3
O
B B CH3CH(OH)CHO
(CH3)3C+ (CH3)3CCH2OH ,
3COCHO
C C CH[HOCH 2- - -C(CH3)3- - -Cl ]
–
HOCH2C(CH3)3
CHS
CH(OH)CH
D D CH3[H3CO- - -C(CH
3 3)3- - -Cl ]
–
H3COC(CH3)3

[S'18 P11 Q22]

C HO2CCH2CH(OH)CO2H
D HO2CCOCOCO2H
23 Primary halogenoalkanes undergo hydrolysis reactions.

31
Which reaction would occur most rapidly if they are all warmed to the same temperature?
A C2H5Br with H2O

B C2H5Br with NaOH(aq)
C C2H5Cl with H2O
D C2H5Cl with NaOH(aq) 8
8
[S'18 P12 Q23]
24 Structural
24 Structural isomerism
isomerism and
and stereoisomerism
stereoisomerism should
should be
be considered
considered when
when answering
answering this
this question.
question.
32
A colourless
A colourless liquid,
liquid, C
C55H
H11 Cl ,, exists
11Cl exists as
as a
a mixture
mixture of
of two
two optical
optical isomers.
isomers.
When heated
When heated with
with sodium
sodium hydroxide
hydroxide in
in ethanol,
ethanol, a a mixture
mixture of
of only
only two
two alkenes
alkenes is
is formed.
formed.
What could
What could the
the colourless
colourless liquid
liquid be?
be?
A
A (CH CH22))22CHCl
(CH33CH CHCl
B
B CH33CH
CH CH22CH
CH22CHCl
CHCl CH
CH33
C
C (CH33))22CHCHCl
(CH CHCHCl CH
CH33
D
D CH33CH
CH CH22CCl
CCl (CH
(CH33))22

si carbocation .
[S'18 P12 Q24]

,
25 When
25
33 When warm
warm water
water is
is added
added to
to halogenoalkane
halogenoalkane X,
X, an
an S 1 reaction
SNN1 reaction occurs.
occurs.
AgNO33(aq)
AgNO (aq) is
is then
then added;
added; a
a yellow
yellow precipitate
precipitate is
is formed.
formed.
\
Iodine
What could
What could be
be X?
X?
A
A 1-chlorobutane
1-chlorobutane
B
B 1-iodobutane
1-iodobutane
C
C 2-chloro-2-methylpropane
2-chloro-2-methylpropane
D
D 2-iodo-2-methylpropane
2-iodo-2-methylpropane
9
[S'18 P12 Q25]
22
26 Which
34 Which statement is not
alcohol will
will correct?
react with an
an acidified
acidified solution
solution of
of potassium
potassium dichromate( VI)) to
dichromate(VI to produce
produce a
a
26 Which alcohol react with
ketone containing
ketone containing six carbon
carbon atoms?
atoms?
A Combustion ofsix
PVC produces a highly acidic gas.
A
A
B 2,2-dimethylbutan-1-ol
2,2-dimethylbutan-1-ol
PVC molecules are saturated.
B
B
C 2-methylpentan-3-ol
2-methylpentan-3-ol
The empirical formula of PVC is the same as the empirical formula of its monomer.
C
C
D 3,3-dimethylpentan-2-ol
3,3-dimethylpentan-2-ol
The repeat unit of PVC is (CHCl CHCl ) .
D 3-methylpentan-3-ol
D 3-methylpentan-3-ol [S'18 P13 Q22]
23 The presence of a halogen in an organic compound may be detected by warming the organic
27 Which
27 Which statement
statement about
about butanone
butanone isis correct?
correct?
Which compound would be the quickest to produce a precipitate?
A Butanone
A Butanone can
can be
be dehydrated
dehydrated by by concentrated
concentrated sulfuric
sulfuric acid
acid to
to give
give CH =CHCH=CH22..
CH22=CHCH=CH
B
B A gives
Butanone
Butanone gives a
a positive B with
positive result
result with Tollens’ C
Tollens’ reagent.
reagent. D
Cl F F Cl
C
C Butanone reacts
Butanone reacts with
with HCN
HCN byby an
an electrophilic
electrophilic addition
addition mechanism.
mechanism.
D
D Butanone reacts
Butanone reacts with
with NaBH to give
NaBH44 to give a
a chiral
chiral product.
product.
Cl Cl F Br
CEDAR COLLEGE Cl F 269 I HALOGENOALKANES

F WS 1
C The empirical formula of PVC is the same as the empirical formula of its monomer.
D
D The repeat
The repeat unit
unit of
of PVC
PVC is
is (CHCl CHCl)) ..
(CHCl CHCl
23 The
23
35 The presence
presence of
of aa halogen
halogen in
in an
an organic
organic compound
compound may
may be
be detected
detected by
by warming
warming the
the organic
organic
compound with
compound with aqueous
aqueous silver
silver nitrate.
nitrate.
Which compound
Which compound would
would be
be the
the quickest
quickest to
to produce
produce aa precipitate?
precipitate?
A
A B
B C
C D
D
Cl
Cl FF FF Cl
Cl
Cl
Cl Cl
Cl FF Br
Br
Cl
Cl FF II FF
[S'18 P13 Q23]
24 Halogenoalkanes
36
24 Halogenoalkanes react
react with
with NaOH(aq)
NaOH(aq) either
either by
by an
an S
SNN11 mechanism
mechanism or
or by
by an
an SSNN22 mechanism.
mechanism.
The mechanism
The mechanism followed
followed by
by the
the reaction
reaction depends
depends on
on the
the structure
structure of
of the
the halogenoalkane.
halogenoalkane.
This question
This question is
is about
about the
the reaction
reaction of
of 3-bromo-3-ethylpentane,
3-bromo-3-ethylpentane, (C (C22H
H55))33CBr.
CBr.
1010
Which statement
Which statement is
is correct?
correct?
2424AnAnorganic
organicmolecule
moleculeW Wcontains
contains3 3carbon
carbonatoms.
atoms.It Itrequires
requires4.54.5molecules
moleculesof ofoxygen
oxygenforfor
A complete
The
complete combustion.
mechanism
combustion. is S 1, due to the stabilisation of an intermediate
A The mechanism is SN1, due to the stabilisation of an intermediate anion by three alkyl
N anion by three alkyl
groups.
groups.
What
What could
could WW be?be?
B The
B The mechanism
mechanism is is S
SNN1,
1, due
due to
to the
the stabilisation
stabilisation of
of anan intermediate
intermediate cation
cation by
by three
three alkyl
alkyl
A A groups.
propane
propane
B B The
C propanoic acid is SNN2, due
mechanism
propanoic acid due to
to the
the stabilisation
stabilisation of
of an
an intermediate
intermediate anion
anion by
by three
three alkyl
alkyl
groups.
C C propanone
propanone
D The mechanism is SNN2, due due to
to the
the stabilisation
stabilisation of
of an
an intermediate
intermediate cation
cation by
by three
three alkyl
alkyl 024
D D groups.
propan-1-ol
propan-1-ol

/
[S'18 P13 Q23]
2525Which
37
25
CompoundJ, J,C15CH1523HBr
Compound 232Br
compound is a secondaryC2l,Clis
, isreacted
reacted
alcohol
alcohol that
with
with
that can
can
anexcess
anbe
be excessof ofatoahot
dehydrated
dehydrated
hotconcentrated
form
to form
concentrated
an
an alkene with
alkene Msolution
withsolution
M 70?of of
= 70?
rr =
sodium
sodium hydroxide
hydroxide in in ethanol.
ethanol. OneOne
of of
thethe products
products is X.
is X.
A B
B CC D
D
excess
excess NaOH NaOH
Cl Cl
Br Br in in ethanol
ethanol
XX OH
OH
Br Br
OH OH
OH OH
OH
compound
compound J J
What
What could
could bebe
thethe skeletal
skeletal formula
formula of of
X?X?
AA BB CC DD
© UCLES 2018 9701/13/M/J/18
9701/13/M/J/18 [Turn over
[Turn over
x x
[W'18 P11 Q25]
2626Sodium
Sodium reacts
reacts with
with 1 mol
1 mol of of compound
compound Y to
Y to produce
produce 1 mol
1 mol of of
H2H 2(g).
(g).
Which
Which compound
compound could
could Y be?
Y be?
A A CHCH 3CH
3CH 2CH
2CH 2CH
2CH 2OH
2OH
B B (CH
(CH 3)3COH
3)3COH
C C CHCH 3CH
3CH 2CH
2CH 2CO
2CO 2H2
H
D D CHCH 3CH(OH)CO
3CH(OH)CO 2H2
H
CO2 CH3 H
25 A halogenoalkane has the molecular formula C5H11Br. The halogenoalkane does not form an
38
alkene when treated with ethanolic sodium hydroxide.
What could be the halogenoalkane?
A 1-bromo-2-methylbutane
B 2-bromo-2-methylbutane
C 3-bromopentane
D bromodimethylpropane

[W'18 P12 Q25]

For each of the questions in this section, one or more of the three numbered statements 1 to 3 may
be correct.
15
Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against
the
36 statements
Element X isthat you consider
a solid. It is foundtoinbe correct).
some SECTION B
fuels.
The responses
Its oxide Y isAformed
to D should
in car be selected
engines. Y ison the basis of
acidic.
A B
Further oxidation of Y to Z can occur in the atmosphere.
C D
Which1,statements
2 and 3 about Y and
1Zand
are2correct? 2 and 3 1 only
14
are only are
1 Molecule Y has lone pairs of electrons. only are is
correct correct correct
The responses A to D should be selected on the basis of correct
2 13
The atmospheric oxidation of Y to Z is a catalysed reaction.
No
381 other
3 is Ycombination
X is organic
an of statements
aAcolourless is used
B gives
gas. that
compound as a correct
a precipitate response.
Cwith aqueous silver Dnitrate. This precipitate
remains undissolved when concentrated aqueous ammonia is added.
Use of the1,Data Booklet may be1 appropriate for some questions.
D
2 and 3 and 2 2 and 3 1 only
37 What aare
Whichisstatements
possible about the
identity only
X?are
photochemical
for only are
chlorination is
of ethane are correct?
correct correct correct correct
31 Which statements step
1 iodomethane
A propagation aboutin the atoms 23Naisand
the mechanism C2H245Mg
• + are
Cl 2correct?
→ C2H5Cl + Cl •.
No other combination
Butane of statements
is present is used as a correct response.
in the products.
1 They have the same number of filled electron orbitals.
2 2-bromobutane
The initiation step is the heterolytic fission of chlorine.
3 2-chlorobutane
38 2An organic
They have the same
compound, number
X, will react of neutrons.
with [W'14 P11 Q38]
calcium metal to produce a salt with the empirical formula
16
3 They are both reducing agents.
CaC H O
4 4 4 .
2 For
38
39 Which compounds
which mixtures produce pent-2-ene
of reagents as either
are the colour one ofdescribed
changes the products, or as the only product, on
correctly?
The heating
What withAbe
responses
could potassium
tothe
D should hydroxide
identitybe X? in ethanol?
of selected on the basis of
32 Which compounds contain covalent bonds?
c
reagents colour change
1 CH 3CH2CH
ethanoic 2CH2CH2Br
A acid B C D
122 1 aluminium
CH 3CHBrCH
butanedioic chloride
pentanal + hot,
2CH2CH3
acid acidified potassium dichromate( VI) orange to green
1, 2 and 3 1 and 2 2 and 3 1 only
2 pentan-2-one + warm
are Fehling’s reagent no
is change
23 CH ammonia
are2CHBrCH
3CH only
2CH3 acid
2-methylpropanedioic only are
3 cyclohexane + cold, acidified potassium manganate( VII) purple to colourless [W'14 P13 Q38]
3 calcium fluoride
3 other
39
No
Which reactions
compounds
combination
have areact
ofwill
coloured
withisorganic
statements HBr product?
to as
used give the compound
a correct R?
response.
40 A1 reaction pathway diagram is shown.
33 Ethylene glycol,
ethanal HOCH2CH2OH, is usedreagent
+ 2,4-dinitrophenylhydrazine Br
as a de-icer. It allows ice to melt at temperatures below
°C.ethanol
38 02Which changes in bonding
+ acidified occur during
potassium the reaction
dichromate( VI) of propanal and hydrogen cyanide?
Which
3 statements
1 ethene + cold are correct?
dilute
A carbon-hydrogen acidified
bond potassium manganate(VII)
is broken.
12 Ethylene glycol changes

An oxygen-hydrogen the
energy
bond extensive network
is formed.
R of hydrogen bonds in ice.
A
40 Propanal will react with hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for
2this
3 Ethylene
reaction isglycol
A carbon-carbonmolecules
sodium cyanide. form hydrogen bonds with other ethylene glycol molecules.
bond is formed.
3 Ethylene glycol molecules

1 will dissolveNaCN
in
2 the water formed from
3 the ice.
39 Which pairs of reagents will react together in a redox reaction?
CH3CH OH 2CHO + HCN extent of reaction
CH3CH2CH(OH)CN
1 CH3CHO + Fehling’s reagent
Which statements
Which abouthave
the reaction of propanal with hydrogen cyanide are correct?
2 C2reactions would
H4 + Br2(aq) this profile?
1 The sodium cyanide provides a stronger nucleophile than HCN.
13 (CH
CH43)+ 3CBr
Cl 2+
(g)NaOH → (CH3)3COH + NaBr
2 The reaction mechanism involves two steps. [S'15 P11 Q9]
2 CH3CH2Br + NaOH → CH3CH2OH + NaBr
4 33Which
40 The
(CH
product
types of the reaction
of reaction has a chiral
are undergone carbon
by CH atom.
2BrCHCH2?
3)3CCH2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl
B
1 hydrolysis
2 free radical substitution
3 2014
© UCLES nucleophilic addition 9701/13/O/N/14
[S'15 P13 Q40]
© UCLES 2015 9701/11/M/J/15

© UCLES 2014 9701/11/O/N/14
Which changes will move the position of the equilibrium to the right?
13 increasing the pressure

phosphorous pentachloride
15
2 increasing the temperature
5 3X
38
35 isusing
The an twice astatine,
organic
element as much catalyst
compound.At,Xisgives a precipitate
below iodine in with aqueous
Group 17 of silver nitrate. Some
the Periodic or all of this
Table.
precipitate remains undissolved when excess dilute aqueous ammonia is added.
Which statements concerning At are likely to be correct?
35 Water is added
What could to anhydrous
be the identity of aluminium
X? chloride to make a 0.1 mol dm–3 solution.
11 2-chlorobutane
It is a dark-coloured solid at room temperature.
Which observations are correct?
22 2-bromobutane
It is a more powerful oxidising agent than14
1 The reaction is endothermic.
iodine.
c
33 iodomethane
The 2responses
The
Its solution
hydrideisisacidic.
thermally stable.
A to D should be selected on the basis of
[W'15 P12 Q38]
3 The solution contains the ion [Al (H2O)6]3+.
6
39
36
Which compounds, on heating with excess concentrated sulfuric acid, produce only one product
Which A of reaction can occur
types B with 1-bromobutane? C D
with molecular formula C7H10?
36 Catalytic
1, converters
2 and 31 are used to modify exhaust emissions
2 from motor vehicles. 1 only
A
1 elimination 1 and 2 2 and 3 3
are only are
Which reactions occur in catalytic converters?
only are is
correct OH
2 hydrolysis correct correct correct
1
1 8 18CH + 12 O
2 2 2 8CO + 9H O
2 OH

No other combination ofNstatements

2 2NO + 2CO
is used as a correct response.
2 + 2CO2
[S'16 P11 Q36]
3 NO + SO3 NO2 + SO2 OH
7 Halogenoalkanes show trends in their physical and chemical properties.
37
OH OH OH
37 Which compounds would produce a carboxylic acid and a ketone when treated with hot,
concentrated, acidified
Which properties KMnO4increase
steadily ? from C2H5Cl to C2H5Br to C2H5I ?
40 Compound Z is heated with concentrated acidified potassium manganate(VII). This produces an
1equimolar
the polarity
2Whatthe
1 2 carbon-halogen
of the
mixture of CO and CH3COCH2CH22CH(COCH3)CH2CO2H. 3
bond
boiling point of the halogenoalkane
C
could be the structural formula of Z?
3 the rate 1of reaction of the halogenoalkane
2 3
with nucleophiles

[S'16 P13 Q37]

38 Ethanal and hydrogen cyanide react together to form a compound used in the production of
38
8 Bromoethane reacts with NaOH in different ways depending on the solvent used.
acrylic fibres. The reaction mechanism 13 involves cyanide ions.
Which statements about these reactions are correct?
37 P and Q are a pair of cis-trans isomers.
CH3 H3C
–
O H3C OH
What mustsolvent used for P and
mainQ?
organic product
:
be the same
C O C H CN C + CN–
1 1 their
© UCLES water
2016 empirical formula ethane-1,2-diol9701/11/M/J/16
CN – H CN H CN
2 2H ethanol
their functional groups ethene
3 3 theirstatements
Which water
skeletal formula ethanol are correct?
about this mechanism
[W'16 P11 Q38]
1 CN– acts as a catalyst.
38
9 The following statements are about the reaction of NaOH(aq) with the three chloroalkanes
shown.
© UCLES
2 2016
CN–is a nucleophile. 9701/11/O/N/16 [Turn over
3 CH3CH
It is an addition 2CHCl CH3
reaction. (CH3)2CHCH2Cl (CH3)3CCl
Which statements are correct?
1 (CH3)2CHCH2Cl reacts with NaOH(aq) by an SN2 mechanism.

2 The tertiary chloroalkane reacts more quickly than the others because the carbon atom
bonded
© UCLES 2015 to the Cl atom is more positive in this molecule.
9701/12/O/N/15
3 The Cl atoms in the three chloroalkanes are attacked by OH–.
[S'17 P11 Q38]
39 For which reactions are the colour changes described correctly?
reagents colour change
1 pentanal + hot, acidified potassium dichromate(VI) orange to green

273
CEDAR 2COLLEGE pentan-2-one + warm Fehling’s reagent noHALOGENOALKANES
change WS 1
3 cyclohexane + cold, acidified potassium manganate(VII) purple to colourless
No other combination of statements
statements is
is used
used as
as aa correct
correct response.
response.
10
38 Which statements help
help to
to explain
explain the
the mechanism
mechanism of
of the
the reaction
reaction between
between 1-chloropropane
1-chloropropane and
and
ammonia?
1 1-chloropropane has
in ammonia.
has aa δ–
δ– chlorine
chlorine atom
atom that
that forms
forms hydrogen
hydrogen bonds
bonds with
with aa δ+
δ+ hydrogen
hydrogenatom
atom
c
2 1-chloropropane is
is aa polar
polar compound
compound with
with aa δ+
δ+ carbon
carbon atom.
atom.
15
3 There is a lone pair
pair of
of electrons
electrons on
on the
the nitrogen
nitrogen atom
atom in
in ammonia.
ammonia.
[M'17 P12 Q38]

37 Which mechanisms are represented in this sequence of reactions?
11 Which compounds react
39 react with
with alkaline
alkaline aqueous
aqueous iodine
iodine to
to give
give aa pale
pale yellow
yellow precipitate
precipitate of
of
CH3CH2CH3
tri-iodomethane? CH3CH2CH2Cl CH3CH2CH2OH CH3CHCH2 CH3CHBrCH2Br
E
11
22
electrophilic addition
butanone
nucleophilic substitution
ethanal
A
OF
propan-2-ol
[M'17 P12 Q39]
38 Propanoic
12
40
40 Which compounds,
Propanoic acid onnaturally
acid occurs
occurs heating as
naturally with
as ethanolic
aa result
result of NaOH,
of the
the produce
bacterial
bacterial more than
fermentation
fermentation of oneand
of milk
milk product
and with
isis partly
partly
molecular formula
responsible
responsible for the C
for the 4H8? of Swiss cheese.
flavour
flavour of Swiss cheese.
D
1 2-bromobutane O
O
2 2-bromo-2-methylpropane
OH
OH
3 1-bromo-2-methylpropane propanoic acid
propanoic13
acid
13
[S'17 P13 Q38]
37 Whichstarting
statements are correct
correct for an
antoS
Sproduce
22 mechanism?
mechanism?
Which starting materials can be used to produce propanoic acid?
37
13 Which
39 Which statements
Substance M is are
refluxed
materials with
can for
beaqueous
used Nsodium
N hydroxide.acid?
propanoic One of the products of this reaction
reacts with
1 alkaline aqueous iodine to give a pale yellow precipitate.
11 CH
CH 33CH
One
22CH
bond
CH OH
CH22is
OHbeing broken at the same time as another bond is being formed.
1 One bond is being broken at the same time as another bond is being formed.
Which
2
22
2 CHcompounds
CH 3CH 2CHO
3CH2CHO
The
could be substance M?
The formation
formation of
of the
the intermediate
intermediate involves
involves the
the collision
collision of
of two
two molecules
molecules or
or ions.
ions. A
1
3
3 CH333CH
CH
CH CO222CN
CH CH3
CN
33 A carbon
A carbon atom
atom in
in the
the transition
transition state
state is
is bonded,
bonded, either
either fully
fully or
or partially,
partially, to
to five
five atoms.
atoms.

2 CH3CO2CH2CH3 [W'17 P12 Q37]

3 HCO CH(CH )
38 Bromoethane
Bromoethane
2 is heated
3heated
2 under reflux
reflux with
with concentrated
concentrated aqueous
aqueous NaOH.
NaOH.
38
14 is under
Which statements
statements areare correct?
40 Which
Propanal will react withcorrect?
hydrogen cyanide to form 2-hydroxybutanenitrile. A suitable catalyst for
this reaction is sodium cyanide.
1 The major product is a primary alcohol.
1 The major product is a primary alcohol.
22 The major
The major reaction
reaction is
is hydrolysis
hydrolysis by anNaCN
by an SNN22 mechanism.
S mechanism.
Be
CH3CH2CHO + HCN CH3CH2CH(OH)CN
3
3 2017
© UCLES
The major
The major product
product would
would be
be the
the same
same ifif the
the NaOH
9701/12/F/M/17
NaOH is
is dissolved
dissolved in
in ethanol.
ethanol.
Which statements about this reaction of propanal with hydrogen cyanide are correct?
© UCLES 2017 9701/12/F/M/17
[W'17 P12 Q38]
39 The CN–M
1Compound
39 Compound Mion
is attacks
is an the propanal
an important
important molecule
ingredient
ingredient to form an intermediate ion.
in perfume.
in perfume.
2 The product of the reaction has a chiral carbon atom.
O
O
–
3 The CN ion is a stronger electrophile than the HCN molecule.
O
O O
O
compound M
compound M
M reacts
M reacts with
with HCN.
HCN.
Which statements
Which statements about
about this
this reaction
reaction are
are correct?
correct?
11 2017
© UCLES AA small
small amount
amount ofof NaOH
NaOH will
will speed
speed up the
up the reaction.
reaction.
9701/13/M/J/17
22 The
The reaction
reaction is
is initiated
initiated by
by the
the transfer
transfer of
of aa proton
proton to
to one
one of
of the
the C=O
C=O groups.
groups.
33 Both of
Both of the
the C=O
C=O groups
groups react
react with
with HCN.
HCN.
Which oxidation states does chlorine show in the products of this reaction?
No other
1 –1 14
combination of statements is used as a correct response.
The 2 +3
responses A to D should be selected on the basis of
38 A reaction
15 3 +1 pathway diagram is shown.
A B C D
1, 2 and 3 1 and 2 2 and 3 1 only
36 In which are
different forms does nitrogen
only are exist in compounds?
only are is
1 correct
bonded correct
by a triple covalent bond correct correct
energy
2 as part of a cation
No other combination of statements is used as a correct response.
3 in an oxidation state of +5
Dr
38 Limonene is found in lemons.
progresspolymers.
37 Poly(ethene) and PVC are examples of addition of reaction
reactions would
Which statements have this reaction pathway diagram?
are correct?
1 On 3)3CBr + NaOH
(CHcombustion, → (CH
PVC can 3)3COH
produce + NaBr
carbon monoxide, carbon dioxide and hydrogen chloride.
2 When
CH3CHpoly(ethene)
2CH2Br + NaOH → inCH
is buried a 3landfill
CH2CHsite,
2OHit +
willNaBr
not significantly biodegrade.
3 The
(CH3empirical
)3CCH2CH formula
2Cl + of
2NHan3 addition
→ (CHpolymer is the
3)3CCH2CH 2NHsame as 4that
2 + NH Cl of the monomer.
limonene [W'17 P13 Q38]
38
39 Organic
16 compound
The compounds X are
below gives
useda toprecipitate when warmed with aqueous silver nitrate. This
make perfumes.
Limonene
precipitateisdissolves
heated with concentrated
when concentratedacidified
aqueouspotassium is added. VII).
ammoniamanganate(
Which compounds will produce a yellow precipitate with alkaline aqueous iodine?
Which compounds
What could X be? are produced?
1 2 3
pg
1
1 CH 3COCH2CH2CH(CH2CO2H)2
1-bromopropane
OH
2
2 CO2-chlorobutane
2
OH
HO O
3 CH COCH CH CH(COCH
3 2-iodo-2-methylpropane
3 2 2 3)CH 2CO 2H
[M’18 P12 Q38]
OH
39
17 Chlorofluoroalkanes have been used as the refrigerant in refrigerators but care has to be taken in
disposing of old refrigerators.
OH
Which statements about chlorofluoroalkanes are correct?
1 C–Cl bonds more readily undergo homolytic fission than C–F bonds. Be
2 Care is taken in the disposal of old refrigerators because of possible ozone depletion.
3 C2H4Cl F is more volatile than C2H6. 15
15
© UCLES 2018 15
9701/12/F/M/18 [Turn over
[S'17 P11 Q39]
37 2-methylpropene can react in more than one way with chlorine.
3737The
40
18 2-methylpropene
2-methylpropene
Mr of compound cancan
X react
react
is in in
72. more
more
The than
than oneway
one
composition way withchlorine.
bywith
mass chlorine.
of X is 66.7% carbon, 11.1% hydrogen
and
One 22.2% oxygen. follows
of the reactions X gives thean orangeshown.
pathway precipitate with 2,4-dinitrophenylhydrazine reagent.
X
© UCLESOne
does
One of of
2017 thethe
not reactions
react follows
with follows
reactions Fehling’s the the pathway
reagent.
pathway shown.
9701/11/O/N/17
shown.

CH3 CH3 CH3

What can CH beCHdeduced from this information?+ CH
3 3
CH3
3
CH3
CH 3
CH2 C + Cl 2 → Cl CH2 C+ + + Cl –
→ Cl CH 2 C + HCl
1 CH Ccarbonyl +compound.
Cl 2 →→ ClCl CH2 C C + ClCl → ClClCH
CH2 CC + HCl HCl
–
CH 2 X C
2 is a + Cl 2 CH 2 + –
→ 2 +
CH3 CH3 CH2
2 X is aCH CH3
ketone. CHCH3 CH2
CH
3
2-methylpropene intermediate 3 product 2
2-methylpropene
3 X is butanone.
2-methylpropene intermediate
intermediate product
product
Which statements about this mechanism are correct?

Which
Which statements
statements about
about this
this mechanismare
mechanism arecorrect?
correct?
1 The intermediate has all carbon atoms in the same plane.
Be
© UCLES 2018 9701/11/M/J/18
1 1 The The intermediate
intermediate has hasallall carbon
carbon atomsininthe
atoms thesame
sameplane.
plane.
2 There is an electrophilic attack on the double bond.
2 2 ThereThere is an electrophilic attack on the double bond.
is an electrophilic attack on the double bond.
3 It is a free radical mechanism.

3 It is a free radical mechanism. [S'18 P11 Q37]
38 The halogenoalkanes listed below all react with NaOH(aq).

38 The
CEDAR halogenoalkanes listed below all react 275
COLLEGE with NaOH(aq). HALOGENOALKANES WS 1
Which reactions proceed mainly by an SN1 mechanism?
Which reactions proceed mainly by an S 1 mechanism?
Which reactions proceed mainly by an SN1N mechanism?
2 There is an electrophilic attack on the double bond.
14
The responses A to D should be selected on the basis of
19
A B C D
Which reactions proceed mainly by an SN1 mechanism?
1, 2 and 3 1 and 2 2 and 3 1 only
are
1 1-iodopropane only are only are is
correct
correct correct correct c
3 2-bromo-2-methylbutane
[S'18 P11 Q38]
38
39 Halogenoalkanes
20 can
3-oxobutanoic acid undergo
can reaction with
be synthesised hydroxideprocess.
in a two-step ions.
si
RBr + OH– → ROH O+ Br – O
,
X Y
The reaction of some halogenoalkanes proceeds by the SN1 mechanism.
Dr
OH
Which statements about the SN1 mechanism are correct?
3-oxobutanoic acid
1 A carbocation is formed which is stabilised by the inductive effect of the alkyl groups present.
What could be the structure of X?
2 Only tertiary halogenoalkanes are hydrolysed in this way.
1 OH
3 The intermediate formed includes a carbon atom with five bonds attached to it.
[S'18 P12 Q38]

Cl O
39 Which statements about 2-methylbutan-1-ol are correct?
2
1 It can give HClOH
(g) on reaction with PCl 5.
2 Br be oxidised
It can O to give an aldehyde.
33 It displays optical isomerism.
H
40 The compound cis-hex-3-enal is responsible for the characteristic smell of cut grass.
O
© UCLES 2018 cis-hex-3-enal
9701/11/O/N/18 [Turn over
Which reagents will react with cis-hex-3-enal?
1 sodium
2 sodium borohydride
3 Fehling’s reagent
© UCLES 2018 9701/12/O/N/18

SECTION
8 A
1 (d) Chloroethene can be polymerised to form a polymer commonly known as PVC.
Draw a diagram of the structure of PVC including three repeat units.
[2]
(e) Chloroethane undergoes a series of reactions as shown in the diagram below.
H H H H
reaction 1
product Q H C C H C C
NaCN
Cl H H H
OH– (aq)
product P
(i) Give the reagent and conditions necessary for reaction 1.
.............................................................................................................................................
....................................................................................................................................... [2]
(ii) Give the skeletal formula of product P.
[1]
(iii) Give the displayed formula and the name of product Q.
....................................................................................................................................... [2]

[S'14 P21 Q4]

[Total: 20]
Permission to reproduce items where third-party owned material protected by copyright is included has been sought and cleared where possible. Every
reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included the
publisher will be pleased to make amends at the earliest possible opportunity.
Cambridge International Examinations is part of the Cambridge Assessment Group. Cambridge Assessment is the brand name of University of Cambridge Local
Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.
© UCLES 2014 9701/21/M/J/14

9
2 (c) (i) Give the structures of the four structural isomers of C4H9Br and identify each as primary,
secondary or tertiary.
........................................................ ........................................................
........................................................ ........................................................
[4]
(ii) Name the isomer of C4H9Br that contains a chiral centre and draw the three-dimensional
structures of the two optical isomers.
name ...................................................................................................................................
structures
[3]
(d) Aqueous silver nitrate solution was added to separate tubes containing chloroethane,
bromoethane and iodoethane. The tubes were heated in a water bath.
A yellow precipitate appeared ﬁrst in the tube containing iodoethane, followed by a cream
precipitate in the tube containing bromoethane and ﬁnally a white precipitate appeared in the
tube containing chloroethane.
Explain these observations.
....................................................................................................................................................
....................................................................................................................................................
....................................................................................................................................................
....................................................................................................................................................
....................................................................................................................................................
.............................................................................................................................................. [2]

10
(e) (i) Give the full name of the mechanism for the reaction between aqueous sodium hydroxide
and bromoethane.
....................................................................................................................................... [2]
(ii) Complete the diagram below to represent this mechanism. Include all necessary curly
arrows, partial charges and lone pairs.
H H H H
H C C Br H C C OH + Br –
H H H H
HO–
[2]
(f) In the past, CFCs such as CF3Cl were widely used as refrigerants.
(i) State a property of CFCs which makes them suitable for use as refrigerants.
....................................................................................................................................... [1]
(ii) State the damaging effect of CFCs in the upper atmosphere.
.............................................................................................................................................
Explain your answer.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
[2]
[S'14 P23 Q4]
[Total: 24]
© UCLES 2014 9701/23/M/J/14

8
43 Halogenoalkanes are useful intermediates in the synthesis of a wide variety of compounds.
(a) 2-bromobutane reacts in two different ways with sodium hydroxide depending on the conditions.
When warmed with aqueous sodium hydroxide, 2-bromobutane produces an alcohol that
exists as a pair of optical isomers.
(i) Give the name of the mechanism of the reaction between 2-bromobutane and aqueous
sodium hydroxide.
....................................................................................................................................... [1]
(ii) Explain why the alcohol produced exists as a pair of optical isomers.
.............................................................................................................................................
....................................................................................................................................... [1]
(iii) Draw the three-dimensional structure of the two optical isomers of the alcohol produced in
(ii).
[2]
Heating 2-bromobutane with ethanolic sodium hydroxide produces a mixture of three alkenes,
two of which are a pair of geometrical isomers.
(iv) Give the name of the mechanism of the reaction between 2-bromobutane and ethanolic
sodium hydroxide.
.......................................................................................................................................
9 [1]
(v) Draw and name the structures of the pair of geometrical isomers formed by reaction of
2-bromobutane with ethanolic sodium hydroxide.
name .............................................................
© UCLES 2015 name .............................................................

9701/22/O/N/15
[2]
(vi) Name the third alkene produced by reaction of 2-bromobutane with ethanolic sodium
hydroxide and explain why it does not show geometrical isomerism.
.............................................................................................................................................
.............................................................................................................................................
CEDAR COLLEGE 280 HALOGENOALKANES

....................................................................................................................................... [2] WS 2
(b) Some reactions involving 2-bromopropane are shown.
name .............................................................
reaction 1 reaction 2 [2]
CH3CHBrCH3 CH3CH(NH2)CH3 X
(vi) 2-bromopropane
Name the third alkene produced by reaction of 2-bromobutane with ethanolic sodium
hydroxide and explain why it does not show geometrical isomerism. reaction 3
reaction 6 hydrolysis
.............................................................................................................................................
HBr
reaction 5 reaction 4
Y CH3CH2CH2OH CH3CH2CO2H
.............................................................................................................................................
(and CH3CH(NH2)CH3
10 which is removed)
....................................................................................................................................... [2]
(b) (i)
Some reactions
State involving
the reagent 2-bromopropane
needed for reaction 1.are shown.
....................................................................................................................................... [1]
CH3CHBrCH3 CH3CH(NH2)CH3 X
2-bromopropane
(ii) State the reagent needed for reaction 2.
reaction 3
reaction 6 hydrolysis
....................................................................................................................................... [1]
HBr
(iii) Give the structural reaction formula
5 of X. reaction 4
Y CH3CH2CH2OH CH3CH2CO2H
(and CH3CH(NH2)CH3
which is removed)
(i) State the reagent needed for reaction 1.
....................................................................................................................................... [1]
(ii) Name
(iv) State the type
reagent needed involved
of reaction for reaction 2.
in reaction 4 and suggest a suitable reagent.
....................................................................................................................................... [1]
.............................................................................................................................................
(iii) .......................................................................................................................................
Give the structural formula of X. [2]
(v) State the name of a solid catalyst for reaction 5.
.......................................................................................................................................
11 [1]
(vi)
© UCLES 2015 Complete the mechanism for the production of 2-bromopropane from Y in reaction
9701/22/O/N/15 6
[Turn over
shown below. [1]
(iv) Name
Includethe thetype of reaction
structure of Y andinvolved in reactionlone
any necessary 4 and suggest
pairs, curly aarrows,
suitable reagent.
charges and partial
charges.
.............................................................................................................................................
Y intermediate
....................................................................................................................................... [2]
(v) State the name of a solid catalyst for reaction 5.

Br
....................................................................................................................................... [1]
H3 C C CH3
H
H
Br
© UCLES 2015 9701/22/O/N/15
[4]
(vii) Give the name of the mechanism in (vi).
....................................................................................................................................... [1]
(viii) 1-bromopropane is a minor product of reaction 6.
Explain why 2-bromopropane is the major product of reaction 6.
.............................................................................................................................................
© UCLES 2015 .............................................................................................................................................

9701/22/O/N/15
.............................................................................................................................................
....................................................................................................................................... [2]
Br
[4]
(vii) Give the name of the mechanism in (vi).
....................................................................................................................................... [1]
(viii) 1-bromopropane is a minor product of reaction 6.
Explain why 2-bromopropane is the major product of reaction 6.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
10
....................................................................................................................................... [2]
5 A reaction sequence is shown.
1010 [W'15 P22 Q4]

[Total: 22]
5 A reaction sequence is shown. O
3 54 A reaction sequence is shown.
H3C CH2 Br H3C CH2 CN H3C CH2 C O
O
bromoethane
H 3C CH2 Brreaction 1 propanenitrile
H 3C CH2 CN reaction 2 H3C CH2 C OH
HC CH2 Br H 3C CH2 CN H3C CH2 C
reaction3 bromoethane reaction propanenitrile propanoic acid
OH
4 bromoethane 5 propanenitrile
reaction reaction propanoic acid OH
H3C reaction
CH2 4 OH H2reaction
C CH 52
LiAl H4 reaction
propanoic acid 3
4 5 LiAl H4 reaction 3
H3C
ethanol CH2 OH ethene H 2C CH2 LiAl H4W reaction 3
H3C CH2 OH H 2C CH2
ethanol ethene W
ethanol
(a) Complete the diagram ethene to show the mechanism of reaction 1. Include all necessary Wcharges,
partial charges, lone pairs and curly arrows.
(a) Complete the diagram to show the mechanism of reaction 1. Include all necessary charges,
(a) Complete
partial the diagram
charges, lonetopairs
show andthe mechanism
curly arrows. of reaction 1. Include all necessary charges,
partial charges,Hlone pairs and curly arrows. H
H H
H 3C C H Br H 3C C H CN + H nor
H 3C C Br H 3C C CN +
H 3C H C Br H 3C HC CN +
H H
H
–
CN H [Turn over
© UCLES 2015 –
CN 9701/22/O/N/15
[2]
–
CN [2]
(b) (i) Give the name of the type of reaction involved in reaction 3. [2]
(b) (i) Give the name of the type of reaction involved in reaction 3.
(b) (i) Give Reduction

.......................................................................................................................................
.
the name of the type of reaction involved in reaction 3.

....................................................................................................................................... [1]
[1]
[S'16 P21 Q5]
The .......................................................................................................................................
infra-red
The infra-red spectrum
spectrum of the propanoic
of the propanoic acid
acidproduced
producedbybyreaction
reaction22isisshown.
shown. [1]
100
The infra-red 100
spectrum of the propanoic acid produced by reaction 2 is shown.
100
transmittance
transmittance
50 50
transmittance
50
0
0 4000 3000 2000 1500 1000 500
4000 3000 2000 1500 1000 500
0 wavenumber / cm –1
wavenumber / cm–1
4000 3000 2000 1500 1000 500
(ii) Describe and explain the main difference between the–1infra-red spectrum of W and that of
(ii) Describe and explain
propanoic acid. the main differencewavenumber / cminfra-red spectrum of W and that of
between the
propanoic acid.
CEDAR COLLEGE
(ii) Describe and explain the main difference 282 between the infra-red spectrum HALOGENOALKANES
of W and that of WS 2
.............................................................................................................................................
propanoic acid.
.............................................................................................................................................
....................................................................................................................................... [2]
.............................................................................................................................................
....................................................................................................................................... [2]
11
11
5 (c)
(c) (i)
(i) Reactions
Reactions 4
4 and
and 5
5 use
use the
the same
same reagent.
reagent.
Give
Give the
the reagent
reagent and
and conditions
conditions needed for reaction
needed for reaction 4.
4.
NAOH Chop
reagent
reagent ...............................................................................................................................
...............................................................................................................................
conditions Heat under reflux
conditions ..................................................................................................................... [2]
..................................................................................................................... [2]
(ii)
(ii) Give
Give the
the conditions
conditions needed
needed for
for reaction 5.
reaction 5.
in ethanol Heat
NaOH under reflux
....................................................................................................................................... [1]
....................................................................................................................................... [1]
(d)
(d) Under
Under appropriate
appropriate conditions,
conditions, ethanol
ethanol and
and propanoic acid undergo
propanoic acid undergo a
a condensation
condensation reaction.
reaction.
(i)
(i) State
State the
the condition
condition necessary
necessary for
for the
the reaction.
reaction.
CONC .
HzSO4 Heat
....................................................................................................................................... [1]
....................................................................................................................................... [1]
(ii)
(ii) Draw
Draw the
the skeletal
skeletal formula
formula of
of the
the organic product of
organic product of this
this reaction.
reaction.
propanol -
Nov
11
I [1]
O [1]
(iii)
ethanol
(iii) Name
Name the
the organic
organic product
product of
of this
this reaction.
reaction.
Ethylprropomoate 12
....................................................................................................................................... [1]
....................................................................................................................................... [1]
(e) V VII) ions in two different ways depending on the conditions,
as shown in the reaction sequence below.
O
hot, concentrated cold, dilute
H3 C CH2 C V T
MnO4 – / H+ MnO4 – / H+
OH
propanoic acidQuestion
Question 5
5 continues over the
continues over the page.
page.
V decolourises bromine water.
VII) is hot and concentrated, propanoic acid is the only organic

product.
VII) is cold and dilute, the organic product is T which has two
chiral centres.
(i) Give the structural formulae of V and T.
UtgCHzUH=CHCHzCH3 CHSCHZCHCOHICHCOHIOHZOHZ
V ................................................................... T .................................................................
[2]
CEDAR COLLEGE
© UCLES (ii) Identify the types of stereoisomerism
2016 shown by V and T.
9701/21/M/J/16 ALKENES WS
over 2
[Turn over
[Turn
© UCLES 2016 9701/21/M/J/16
V ................................................................... T .................................................................
[2]
[Total: 15]

carbonyls
11
(c) (i) Complete the reaction mechanism for reaction 5. Include all relevant lone pairs, curly
arrows, charges and partial charges. 8
-87
4 In each section of this question the structural CH3YH2
8
formula of an organic compound is shown. For each
CH 3CHanswer
compound the questions about it. OH
2 It 8
4 In each section of this g question thenostructural
.
c
formula of an organic compound is shown. For each
Canswer O of CH 3CH 2is shown. C CN
/
-
4compound
(a) In
CHeachCH section
CHBrCH thethis
questions
question about
the it.
structural formula of an organic compound For each
compound ht
3 2 3
answer the questions about it.I
H H
(a) (i)
CH3Name
. .
CH2CHBrCH this compound.
3 H
NC(a) CH3CH2CHBrCH3
−
(i) .......................................................................................................................................
Name this compound. [1]
[4]
(i) Name this compound.
(ii) .......................................................................................................................................
The This
product compound
of reaction shows stereoisomerism.
5 exhibits stereoisomerism. [1]
....................................................................................................................................... [1]
HE
(ii) Draw
(ii) This compound
Draw the two
the shows stereoisomerism.
two stereoisomers in the
the conventional
conventional way. way.
(ii) This compound shows stereoisomerism.
Iii:
OH
'd
Draw the two stereoisomers in the conventional way. OH
Draw the two stereoisomers in the conventional way.
§
+
CHzCHz .
ik
a '
CHIH 's
[2]
I
[2]
[2]
[2]
E (iii) Give the structures of three other structural isomers of C4H9Br.
(iii) Suggest why a mixture of the two stereoisomers is formed by reaction 5.
(iii) (iii)
Give the the
Give structures
structures of three
of three other
otherstructural
structural isomers
isomersofofCC 4HH 9Br.
4 9Br.
Nucleophile can attach itself from either side
.............................................................................................................................................
as the
carbonyl is planar
.............................................................................................................................................
.
....................................................................................................................................... [2]
C
[3]
i
[Total: 13]
[3]
[3] P21 Q5]
[S'16
(b) (C2H5)3CBr
I
6 (b) (b)(C2H (C H5)3CBr
5)23CBr
(i) Name this compound.
C
(i) (i) Name thisthis compound. C C c -
Name compound.
-
-
-
....................................................................................................................................... [1]
3- bromo ethyl pentane
I
3-
.......................................................................................................................................
.......................................................................................................................................
-
.
[1]
[1]
(ii) (C2H5)3CBr reacts with aqueous OH–. Br
(ii) (ii)
(C2H (C)2HCBr
5 3
5)3CBr reacts
reacts with with aqueous
aqueous OHOH – –.
.
Complete the mechanism for this reaction including all necessary curly arrows, charges,
partialComplete
Complete thethe
charges and mechanism
lone pairs.
mechanism forforthisthis reaction
reaction includingallallnecessary
including necessarycurly curlyarrows,
arrows, charges,
charges,
partial charges and
partial charges and lone pairs. lone pairs.
CH3CH2 CH3fHz
CH3CHCH32CH2 At CHFa OH
CH3CH2C Br
-
C
EH
'
→ CASH,
-
CH CH C Br C ①
-
CH3CH32C 2 Br CASH
-
I
It
CH3CH2 I
CH3CH2 CHZCHZ
CH3CH2 CHZCHZ [3]
[3]
[3]
(iii) What type of mechanism occurs in (ii)?
© UCLES 2016 (iii) What type of mechanism occurs in (ii)?
(iii) What type of mechanism occurs in (ii)?
Nucleophilic substitution .
....................................................................................................................................... [1]
....................................................................................................................................... [1]
....................................................................................................................................... [1]
© UCLES 2016 2016
© UCLES 9701/22/O/N/16
9701/22/O/N/16
© UCLES 2016 9701/22/O/N/16

9
(c) CH3CH2CH2CHBrCH3
(i) Give the reagents and conditions necessary for the conversion of this compound into a
mixture of alkenes.
NaOH in ethanol .
.............................................................................................................................................
Heat under reflux
....................................................................................................................................... [2]
(ii) Give the name of the mechanism for the conversion in (i).
Elimination .
....................................................................................................................................... [1]
(iii) Draw the skeletal formulae of the three alkenes produced by the conversion in (i).
[3]

[W'16 P22 Q4]

[Total: 17]

11
37 (a) A series of reactions starting from 1-bromobutane is shown.
HCN and KCN reaction 1

1-bromobutane P CH3 (CH2 )3 CO2 H
OH– (aq) reaction 2
polymer
but-1-ene
Q
R
(i) Draw the displayed formula of compound P.
H H H It
I
I I I
H -
C -
C -
C -
C -
CN
I l I
I
H H H -
H
[1]
(ii) Identify the reagent(s) and conditions for reactions 1 and 2.

Ail Hzsoy a heat
reaction 1 ............................................................................................................................
.
NaOH in ethanol heat

reaction 2 ............................................................................................................................
,
[2]
(iii) Draw the structure of the repeat unit of polymer Q.
H
it
C2H5
I I
H It
12 [2]
(b) Complete the reaction scheme to show the mechanism of the reaction of 1-bromobutane with
OH–(aq) to produce R.
Include all necessary charges, dipoles, lone pairs and curly arrows and the structure of R.
CH3CH2CH2
H C Br
–
OH
© UCLES 2017 9701/22/F/M/17 [Turn over

[3]
H H It It
I
I I I
H -
C -
C -
C- C- CN
I I I
I
H H H -
A
feet
ft 4245
H It
Totem
CHGCHZ
/CHzCH2OH3
t a
to
-
→
-
*
ij%Ba.at thiamin
mi
-
OH (aq) to produce R.
Include all necessary charges, dipoles, lone pairs and curly arrows and the structure of R.
6*0,86
I
¥
CASH /CHzCH2OH3
¥aHBBamE
CH3CH2CH2
8th por
d-
HO C
:*
→
-
-
H C Br
HE
.
H imam
–
OH
SAGE
imi
[3]

[M'17 P22 Q3]

(c) But-1-ene reacts with steam as shown to form a mixture of two structural isomers, S and T.
reflux
S U
Cr2O7 2– / H+
major product
but-1-ene + steam
minor product
S VI) to form compound U.

S and U both react with alkaline aqueous iodine.
(i) Identify the type of reaction that occurs when but-1-ene reacts with steam.
....................................................................................................................................... [1]
(ii) State what can be deduced about the structure of S from its reaction with alkaline aqueous
iodine.
....................................................................................................................................... [1]
© UCLES 2017 9701/22/F/M/17

8
8 (b) Complete the diagram to show the SN2 mechanism of reaction 1. R represents the CH3(CH2)2
group.
Include all necessary charges, dipoles, lone pairs and curly arrows.
H H
It I -
R '
C Br R C O H
of H
v
H
• a
HO
[2]
(c) 2-bromo-2-methylpropane is a tertiary halogenoalkane that is a structural isomer of

1-bromobutane.
(i) Define the term structural isomer and name the three different types of structural isomerism.
same molecular formula but different
definition .............................................................................................................................
,
structural formula
.............................................................................................................................................
.
.............................................................................................................................................
.............................................................................................................................................
types of structural isomerism

Chain
1 ..........................................................................................................................................
Positional
2 ..........................................................................................................................................
Functional
3 ..........................................................................................................................................
[4]
(ii) 2-bromo-2-methylpropane is treated with the same reagents as in reaction 1.

Methylpropan-2-ol is formed.
Identify the mechanism for this reaction.

Explain why this reaction proceeds via a different mechanism from that of reaction 1.
Snl
mechanism .........................................................................................................................
2- bromo 2 is able to form
methylal Kane
explanation .........................................................................................................................
-
a carbocation which is stable

tertiary
a
.............................................................................................................................................
,
intermediate because of the 3 Alkyl groups

.............................................................................................................................................
.
In reaction I the oalkome doesnt form

halogen
.............................................................................................................................................
,
A stable embrocation and hence

undergoes
.............................................................................................................................................
[3]
Smd .
[W’17 P21 Q3]
© UCLES 2017 9701/21/O/N/17

8
49 Some reactions are shown, based on methylpropan-2-ol, (CH3)3COH.
(CH3 )3 CBr (CH3 )3 COH (CH3 )2 C=CH2
reaction 2
reaction 4
(CH3 )3 CBr and (CH3 )2 CHCH2 Br
(a) For each of the reactions state the reagent(s), the particular conditions required, if any, and the
type of reaction.
For the type of reaction choose from the list.

Each type may be used once, more than once or not at all.
Each reaction may be described by one or more than one type.
hydrolysis dehydration substitution
oxidation addition condensation
reaction reagent(s) and conditions type(s) of reaction
P and Bk
1 Red substitution
2 NaOH cage substitution
HzS04
3 conc .
Dehydration
4
Hmr in
organic Addition .
solvent
[5]
(b) Draw a diagram to show the SN1 mechanism of reaction 2.

Include all necessary charges, dipoles, lone pairs and curly arrows.
-0
Br
guts
CHS
HE
my
\
IIE c
→
Ho
-
→ -
,
ax .
*
.
HE ! Wb
OH
Uts
Utz
[3]
© UCLES 2017 9701/22/O/N/17

3 ..........................................................................................................................................
[4]
(ii) 1-bromobutane is treated with the same reagents as in reaction 2. Butan-1-ol is formed.
Identify the mechanism of this reaction.

Explain why this reaction proceeds via a different mechanism from that of reaction 2.
SN 2
mechanism .........................................................................................................................
No stable carbocation intermediate
explanation .........................................................................................................................
formed it doesn't
as have
enough alkyl
.............................................................................................................................................
groups
and hence is not stable .
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
[3]
(d) The product of reaction 3, methylpropene, does not show stereoisomerism.
(i) Give two reasons why methylpropene does not show stereoisomerism.
°
NO Chiral center
.............................................................................................................................................
identical
As it has two
methyl
.
.............................................................................................................................................
groups
....................................................................................................................................... [2]
[N'17 P22 Q4]

A It is a gas.
B It is a reducing agent.
C It reacts with oxygen to form sulphur trioxide.
D
It reacts with water to form an acidic solution.
SECTION A
19
1 The anaesthetic halothane, CF3CHBrCl , is made industrially as shown below.
HF Br2
CCl2=CHCl ⎯⎯→ CF3CH2Cl ⎯⎯→ CF3CHBrCl
stage 1 stage 2
What type of reaction is occurring in stage 2?
A electrophilic addition
B electrophilic substitution
9
C free radical substitution 9
25 Which reaction is not an electrophilic addition?
D nucleophilic
24 Compound addition
X undergoes the following reactions.
A CH2 =CH2 + HI ⎯→ CH3 CH2 I 8 [S'02 Q19]

NaOH(aq) / heat 2– +
Cr2O7 , H (aq) / heat
B4H9CH
C Br ⎯⎯⎯⎯⎯⎯⎯⎯→ O ⎯⎯⎯⎯⎯⎯⎯⎯⎯→
C4H10CHBrCH C4H8O only
3 CH=CH2 + Br2 ⎯→ CH Br
23
2 2-Bromopropane, (CH3 )2CHBr, may be used2 as the starting point for making (CH3 )2CHCO2H.
3
X conc H2 SO4
C CH3 CH=CH2 + H2 O ⎯⎯⎯→ CH3 CH(OH)CH3
Whichis of
What X?the following sequences would be most suitable?
D CH 3 CHO + HCN ⎯→ CH3 CH(OH)CN
9701/1/M/J/02
AA (CH3 )2CHBr → (CH3 )2CHOH → (CH3 )2CHCO2H
1-bromobutane
26 B
The reaction scheme outlines the production of one of the monomers of nylon 66 from
3 )2CHBr → (CH3 )2CHCN → (CH3 )2CHCO2H
B 2-bromobutane
(CH
compound X.
(CH3 )2CHBr → (CH3 )2CHOH → (CH3 )2CHCN → (CH3 )2CHCO2H
CC 1-bromo-2-methylpropane
KCN reduction
D compound
(CH ) CHBrX→ (CH ) CHCNNCCH
→ (CH CH) CH2 CH→
CHOH CN
(CH H2 N(CH2 )6NH2
D 2-bromo-2-methylpropane 3 )2CHCO2H
in ethanol 2 2 2
3 2 3 2 3 2
[S'02 Q23]
24 Which
Whichcompound
substance could be X? exhaust results from incomplete combustion of a hydrocarbon fuel?
in (CFCs)
a vehicle
25
3 Chlorofluorocarbons have been widely used in aerosol sprays, refrigerators and in making
foamed plastics, but are now known to destroy ozone in the upper atmosphere.
A BrCH2 CH2 CH2 CH2 Br
A CO B H2O C N2 D NO
Which
B CHof2 =CHCH=CH
the following2 will not destroy ozone, and therefore can be used safely as a replacement
for CFCs?
25 C HOCH
Which 2 CH2 CH
compound 2 CH
on 2 OH with hydrogen cyanide produces a compound with a chiral centre?
reaction
A CHBr
D HO2 CCH 3 B CCl
CH2 CH2 CH23COCBr3H C CHClFCClF2 D CH3CH2CH2CH3
A CH3 CHO2 2
[W'02 Q25]
26 B CH3 CH
Oxidation 2COCH
of an 2CH
alkene Y 3gives a diol; further oxidation gives a diketone.
27
4 Chlorofluoroalkanes, commonly known as CFCs, undergo homolytic fission by ultraviolet
C CH3 CO
irradiation CHstratosphere.
in 2the 3
What could be Y?
D HCHO
Which radical could result from this irradiation of CHFClCF2 Cl ?
A CH3CH=C(CH3)2
A (CH
CHFCl
·
CFCl =CH
26 BAn organic
) CHCH 2 will decolorise dilute acidified aqueous potassium manganate(VII) on
· 3 2 compound
Bwarming,
C but
HClCF will
Cl
C C6H5CH=2 CHC6H5 not decolorise bromine water.
·
C
D CHFCF
(C Cl
=CHCH
What 6H5)2C
could 2the organic
3 compound be?
· FClCF
D C 2 Cl
A butane
27 Burnt sugar has a characteristic smell caused partly by the following compound. It has two
[S'03 Q27]
B ethanol Q and
28 functional groups
In its reaction withindicated
sodium, 1bymol of a R.
compound X gives 1 mol of H2 (g).
C ethene
Which compound might X be? Q O
D ethanoic acid R
A CH3 CH2 CH2 CH2 OH CH3 C CHO
27 B (CH3 )3 COH
A compound X has all of the following properties:
When this compound is tested in a laboratory with 2,4-dinitrophenylhydrazine and Fehling’s reagent,
C CH
which 3 CH 2 CH
functional CO2 H are responsible for positive tests?
2groups
it is a liquid at room temperature and atmospheric pressure;
DCH3 CH(OH)CO2 H
it does not mix completely with water;
2,4-dinitrophenylhydazine Fehling’s reagent
it does not decolorise acidified potassium manganate(VII).
A Q and R Q and R
What
B
could X be?
R only Q and R
A C17H34 B C17H36 C C19H38 D C19H40
23
5 1,2-Dibromo-3-chloropropane (DBCP) has been used in the control of earthworms in agricultural
land.
What would be the best synthesis of this compound?
A CH3CH2CH2Cl + 2Br2 → DBCP + 2HBr

B CH3CHBrCH2Br + Cl2 → DBCP + HCl
C CH2=CHCH2Cl + Br2 → DBCP
D ClCH2CH=CH2 + PBr5 → DBCP + PBr3
7
9
[W'03 Q23]
24
20 Each of the
Bromine andfollowing
propenecompounds
undergo anisaddition
effectivereaction.
as a refrigerant.
6 A possible mechanism of the hydrolysis of 2-chloro-2-methylpropane is shown.
26
The release
Which of whichofone
is a property theofproduct?
these causes the greatest depletion of the ozone layer?
CH3 CH3
A B CH3OCH3 C D
A It exists in cis-trans isomers.
CCl2F2 CH3CHF2 CH3CH2CH3
slow _
B CH C
It is more volatile than3 propene. Cl CH3 C+ + Cl
25 1,1-Dichloropropane reactscentre.
C It possesses a chiral with aqueous sodium hydroxide in a series of steps to give propanal.
CH3 CH3
D It possesses hydrogen bonding. NaOH(aq)
CH3CH2CHCl2 ⎯⎯⎯⎯→ CH3CH2CHO
CH3 CH3
21 What is the mechanism
Buta-1,3-diene of theobtained
is currently first stepfrom
of this reaction?
fossil fuel sources. In future it may be obtained from
ethanol, which can be produced from non-food _
agricultural
fast crops. The sequence of reactions is
CH3 C+ + OH CH3 C OH
A electrophilic substitution
as follows.
step 1
B elimination CHstep 2 step
CH3 3
3
CH3CH2OH CH3CHO CH3CH(OH)CH2CHO CH2=CHCH=CH2
C nucleophilic substitution
Which diagram represents the reaction profile for this mechanism? buta-1,3-diene
D oxidation 7
Which termAcould be used to describe
B step 1? C D
19 Nitrogen dioxide and sulphur dioxide have some properties in common.
A condensation
Which property is shown by one of these compounds, but not by the other?
energy
energy
energy
energy
B dehydration 9701/1/O/N/03
A forms ‘acid-rain’
C dehydrogenation
B is a reducing agent
D hydrogenation
C is insoluble
reaction in water
path reaction path reaction path reaction path
22 D
Use is
ofused as a Booklet
the Data food-preservative
is relevant to this question. [S'04 Q26]
7 Ethene
27 reacts
Which bond withstructure
in the aqueousbelow
bromine to give
has the twobond
lowest products, CH2BrCH2Br and CH2BrCH2OH.
energy?
20 Which molecule is planar?
H
Which statement is correct for these products? F
A NF3
A Both products are obtained in this A C
B by electrophilic substitution.
reaction
B C2Cl 4 H C C Cl
B
C Both
C products are obtained in this reaction by D
nucleophilic addition.
3H 6
C Both products can be hydrolysed toHform the

H same diol.
D C 3H 8

D Both products can form hydrogen bonds with water. [W'04 Q27]
8 Which
23
21 Ethanal,
of CH 3CHO,
these canapplies
always be reduced using NaBH4 in aqueous ethanol.
to a nucleophile?
A
ThisItisattacks a doubleaddition
a nucleophilic bond. reaction.
B It has a lone pair of electrons.
What could be the first step of this mechanism?
C It is a single atom.
A attack of an H– ion at the carbon atom of the carbonyl group

D It is negatively–charged.
B attack of an H ion at the oxygen atom of the carbonyl group
[S'04 Q21]
C attack of an H+ ion at the carbon atom of the carbonyl group
CEDAR 292
22 Compound P displays cis-trans isomerism and gives a red-brown precipitate with Fehling’s
COLLEGE HALOGENOALKANES WS 3
D attack of an H+ ion at the oxygen atom of the carbonyl group
solution.
What is P?
C phosphorus pentachloride
D sodium
9 Under the Montreal Protocol the use of chlorofluorocarbons is to be phased out. Fluorocarbons
21
are often used to replace them. One chlorofluorocarbon which was widely used as a solvent is
CCl2FCCl F2 and large stocks of it remain. One process to use up these stocks is to convert it into
the fluorocarbon CH2FCF3 by the following route.
7
step 1 step
92 step 3
CCl2FCCl F2 CCl3CF3 9 CCl 2
FCF 3
CH2FCF3
20 When
22 What isbromine
the number of isomers
reacts of C2H2inClan
with propene 2 including solvent isomers?
organiccis-trans at room temperature, what is the
What
the type
19 mechanism
In ofby
Contactreaction
process
which is for
the step 1?production
the
bromine of sulphuric
attacks the propene?acid, sulphur dioxide is mixed with air and
A 2 over a vanadium(V) B 3 C 4at about 450 D o 5 a pressure slightly above
passed oxide catalyst C and
A elimination
electrophilic
atmospheric addition
pressure.
free radical substitution
21 B electrophilic
Which substitution
hydrocarbon, on treatment
2SO2 + with
O2 hot acidified
2SO potassium manganate(VII), would give
3 ; ∆H negative
Cethanoic acid only?
isomerisation
nucleophilic addition
What affects the choice of conditions for this reaction?

DA nucleophilic
CH3CH CH substitution
2
A A lower temperature would not raise the concentration of SO3 at equilibrium. [S'05 Q21]
BB At CHa3CH
lower CHCH 3
temperature of F
300 o
C the V2 used
O5 catalyst would not be effective.
10
23 Dichlorodifluoromethane, CCl , has
2 2 been in aerosol propellants and as a refrigerant.
o
C At CH450
3
C nitrogen and oxygen from the air combine to form nitrogen oxides which are
Which statement helps to explain
needed as additional why dichlorodifluoromethane is chemically inert?
catalysts.
C C CHCH3
A
D The CH3carbon-fluorine
The
© UCLES 2005
heat generatedbond energy
by the raises the temperature of the catalyst bed to 600 o C at
is large.
reaction 9701/01/M/J/05
which temperature the reaction begins to take place.
B The carbon-fluorine bond has a low polarity.
CH3 CH3
C C C
D Fluorine is highly electronegative.
20 In which class of compound, in its general formula, is the ratio of hydrogen atoms to carbon
CH CH3
D
atoms 3 highest?
Fluorine
the compounds are non-flammable.
[S'05 Q23]
A alcohols
11 B
22
24 In the upper
Under atmosphere
identical
aldehydes
conditions,chlorofluoroalkanes (CFCs)byare
even though it proceeds thebroken
same down to give reaction
mechanism, chlorine 1radicals
is faster
but not
than fluorine
reaction 2. radicals.
C carboxylic acids
What is the1best explanation
reaction CH3CHBrCH for
3 +this?
NaCN → CH3CH(CN)CH3 + NaBr
D halogenoalkanes
A reaction 2 is more
Fluorine CHBrCH3 + NaI than
CH3electronegative → CH 3CHICH3 + NaBr
chlorine.
B Fluorinewill
radicals are less stable than chlorine radicals.
21 What
What factor explain
is the total number this result?
of different chloroethanes, formula C2 H6-nCln, where n can be any
integer
Thefrom
C The C–F1 bond
to 4?
A C I bondisisstronger thanbond
a stronger the C–Cl bond.
than the C Br bond.
D
A
B 4The C
The chlorine atom
N bondB isisa6larger than
stronger the C
bond fluorine
than7theatom.
C I bond.D 8
[W'05 Q22]
C The cyanide ion is a stronger nucleophile than the iodide ion.
12
22
23 Which reaction
An amine is an example
is produced of nucleophilic
in the following substitution?
reaction.
D The cyanide ion is a weaker nucleophile than the iodide ion.
A CH3 CH2 Br → CH2 =CH2 + HBr
C2H5I + 2NH3 → C2H5NH2 + NH4I
B CH2 =CH2 + HBr → CH3 CH2 Br
What is the mechanism?
C C3 H7 Br + H2 O → C3 H7 OH + HBr
D C2 H6 + Br2 → C2 H5 Br + HBr
[W'06 Q22]
C nucleophilic addition
D nucleophilic substitution

C The C–F bond is stronger than the C–Cl bond.
C
D ethane
The + bromine
chlorine atom is larger than the fluorine atom.
D ethanol + phosphorus pentachloride
13 An amine is produced in the following reaction.

23
24 Light initiates the following reaction.
C2H5I + 2NH3 → C2H5NH2 + NH4I
alkane + chlorine → chloroalkane + hydrogen chloride
What is the mechanism?
What happens to chlorine in this photochemical reaction?
A heterolytic fission to give an electrophile
B
B
electrophilic substitution
homolytic fission to give an electrophile
C
C nucleophilic addition
heterolytic fission to give a free radical
D
homolytic fission to give a free radical
[W'05 Q23]
14
25 High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes, commonly
known as CFCs.
Which radical could result from this irradiation of CHFClCF2Cl?
A CHFClCFCl
B 2005
© UCLES CHClCF2Cl 9701/01/O/N/05 [Turn over
C CHFCF2Cl
D CFClCF2Cl

9 [S'06 Q25]
15
20 Under the Montreal Protocol, the manufacture of chlorofluorocarbons has been phased out, and
they are being replaced by fluorocarbons.
© UCLES
One2006
chlorofluorocarbon which was widely9701/01/M/J/06
used as a solvent is CCl2FCCl F2. Large stocks of it
remain. One process to use up these stocks is to convert it into the fluorocarbon CH2FCF3 by the
following route.
step 1 step 2 step 3

CCl2FCCl F2 CCl3CF3 CCl2FCF3 CH2FCF3
What type of reaction is step 2?
B free radical reduction
C isomerisation
10 [S'05 Q20]
21 Which
16
24 Which reagent could bethe
term describes used to convert
action CH3COon
of NaOH(aq) 2CH3 into ClCH2CO2CH3?
a bromoalkane?
A concentrated hydrochloric acid at 100 °C
A acid-base reaction
B phosphorus pentachloride at room temperature
C sulphur dichloride oxide (thionyl chloride, SOCl2) at 50 °C
C elimination of HBr
D chlorine in bright sunlight at 100 °C
[S'07 Q24]
22 In which reaction is a carbocation (carbonium ion) an intermediate?
25 X and Y are the reagents required to convert 1-bromopropane into butanoic acid.
A CH2=CH2 + Br2 CH2BrCH2Br
H H H H H H H H H O
X CH CH OH + NaBr Y
H B CCH3CH
C 2BrC+ NaOH
Br 3H 2 C C C CN H C C C C
C HCH3CH
H 3 +H
Cl2 H
CH3CH2Cl + HCl H H H H H OH
CEDAR COLLEGE CN– 294 HALOGENOALKANES WS 3

D CH
What areCHO
3 + HCN identities
the correct CH3CH(OH)CN
of X and Y?
X Y
C elimination of HBr
D D nucleophilic
nucleophilicsubstitution
substitution
2525X X
17 and Y Yare
and arethe
thereagents
reagentsrequired
requiredtotoconvert
convert1-bromopropane
1-bromopropaneinto
intobutanoic
butanoicacid.
acid.

H H H H H H H H H O
H H H H H H H H H O
X Y
H C C C Br X H C C C CN Y H C C C C
H C C C Br H C C C CN H C C C C
H H H H H H H H H OH
H H H H H H H H H OH
What are the correct identities of X and Y?
What are the correct identities of X and Y?
X Y
X Y
A NH3 HCl(aq)
A NH3 HCl(aq)
B KCN in C2H5OH NaOH(aq)
B KCN in C2H5OH NaOH(aq)
C KCN in C2H5OH HCl(aq)
C KCN in C2H5OH HCl(aq)
D

HCN NaOH(aq)
D HCN NaOH(aq)
99 [S'07 Q25]
18
2526 Chlorofluoroalkanes,
26
An alcohol with molecular formula
CFCs, for can CnHused
be 2n+1OHashas
as a chiral carbon
refrigerants,
refrigerants, atompropellants
aerosol
aerosol but does not
propellants react
and
and firewith
fire
26 Lactic
An acid
−
alcohol
MnO 4 / H .
occurs
+
with
extinguishers.
naturally,
molecular example
formula C n H inOH
2n+1
sour milk.
has a chiral carbon atom but does not react with
MnO −4 / H+. H
CFCs
Whatsuch asleast
is the F and CCl
CCl33number F22 are more
of 22carbon atomsstable than
suchthan chloroalkanes
chloroalkanes
an alcohol such as
such as CCl
could possess? CCl44..
What is the least number of carbon atoms H such
O an alcohol
O
could possess?
What
A is 5 the reason for B
their6greater stability?C 7 D 8
A 5 B 6
A Fluorine has a higher first ionisation C
H energy
C C than
7
thanC chlorine.
chlorine.
D 8
27 B Which reagent
Fluorine givesare
radicals themore
same visible
stable H chlorine
result
than H O H and with propan-2-ol?
with propanal
chlorine radicals.
radicals.
27 Which reagent gives the same visible result with propanal and with propan-2-ol?
C A The
lactic acid
2,4-dinitrophenylhydrazine
C–F bond energy is larger reagent bond energy.
than the C–Cl bond energy.
A 2,4-dinitrophenylhydrazine reagent
D B The
acidified
C–F bondpotassium
is moredichromate(VI) bond.
polar than the C–Cl bond.
What is a property
B acidified potassium of lactic acid?
C sodium
dichromate(VI) [W'07 Q25]
19
26 A
C D It decolourises
Butanedioic
sodium acid
Tollens’ aqueous
occurs
reagent bromine
in amber, rapidly.
algae, sugar cane
lichens, sugar cane and
and beets.
beets. ItIt may
may be
be synthesised
synthesised in
in
two steps from 1,2-dibromoethane.
B
D It is insoluble
Tollens’ in water.
reagent
step 1 step 22
step
C It reducesBrCH CH Br
Fehling’s reagent.
22 22 X HO22CCH
HO CCH22CH
CH22CO
CO22H
H
D Two molecules react with each other in the presence of a strong acid.
Which reagents could be used for this synthesis?
27 Which compound
stepwould
1 undergo nucleophilic
step 2 addition?
A A bromoethane, C2H5Br
HCN(g) HCl (aq)
B Bethanal,
HCOCH23Na(aq)
CHO HCl (aq)
© UCLES 2007 9701/01/M/J/07
C C ethane,
© UCLES 2007
KCN(aq/alcoholic)
C2H6 H22SO44(aq)
9701/01/M/J/07
D Dethene, NaOH(aq)
C2H4 K22Cr22O77 / H22SO44(aq)

(aq)
[S'11 P11 Q21]
20
27 Which
28 Which reaction
compound willundergoes
distinguish an
between and
a primary and
SN1 substitution aa secondary
secondary alcohol?
reaction? alcohol?
warming with H++ / MnO−4−4

A
A
CH 3CH2 CH2 Br
+ 2−
warming with H+ / Cr22O 727−
(CH3)3CCH2 I
B
B
C (aq)
dehydration, followed by reaction with Br22(aq)
CH3 Cl
D (or Tollens’)
oxidation, followed by reaction with Fehling’s (or Tollens’) reagent
reagent
C
D CH2 =CHCl

[W'10 P11 Q28]

diagram.
What is the main product formed initially?
A CaO HO
B Ca(OH) CH23 C CaSO3 HO D CaSOCH3 4
C
C I
CH2 CH2
CH 2 CH 2
21
20 Which pair of reaction types is illustrated II reaction sequence
by the
CH2 C
below?
CH2OH CO2H O
HI in CH3CO2H O
NaOH(aq)
CH3CH=CHCH3 CH3CH2CHICH3 CH3CH2CH(OH)CH3
What names are used to describe the pair of interchanging reactions I and II?
A
A electrophilic
condensationaddition and electrophilic substitution
and addition
B
B electrophilic addition
dehydrogenation and and nucleophilic substitution
hydrogenation 9
C
C nucleophilic
esterificationaddition and electrophilic substitution
and hydrolysis
21 What always applies to a nucleophile?
D
D nucleophilic
neutralisationaddition and nucleophilic substitution
and acidification
A It attacks a double bond.

[S'08 Q20]
B It has a lone pair of electrons.
22
25 Halogenoalkanes are important molecules in organic synthetic reactions. In particular they
undergo
C It is aa single
range atom.
of nucleophilic reactions.
D It isreaction
Which negatively charged.
proceeds only by an SN1 mechanism?
A CH3CH2Br + NH3
22 Trichloroethanoic
© UCLES
acid, –CCl3CO2H, is used in cosmetic surgery to perform a ‘chemical peel’ to
B 2008
CH3dead
remove CH2CH 2I + OH
skin.
9701/01/M/J/08
C CH3CHBrCH3 + NH3
Trichloroethanoic acid can be made by reacting chlorine with ethanoic acid.
D (CH3)3CI + OH–
What is the mechanism of this reaction? 8 [S'08 Q25]
23
23 A alcohol
26 Four
An electrophilic additionformula1-bromobutane
drops ofofmolecular
1-chlorobutane, C4H10O2 contains two
and OH groups and
1-iodobutane has
were putanseparately
unbranched carbon
into three
atom chain.
test-tubes containing
B electrophilic 1.0 cm3 of aqueous silver nitrate at 60 °C.
substitution
+
A
Onhydrolysis
C reaction
free radical
reaction an occurred.
excess of(Rhot
addition
with MnO−4 / H
represents the butane
this chainisC4converted
alcohol H9– and X into
the halogen atom.)of
a compound
molecular formula C4H6O4.
D free radical substitution
To which two carbon atoms in the chain of the alcohol are the two OH groups attached?
The rate of formation of cloudiness in the tubes was in the order RCl < RBr < RI.
23 Polymerisation
A 1st and 2ndof chloroethene gives PVC.
Why is this?
How
B 1stdoes
andthe carbon-carbon bond in PVC compare with that in chloroethene?
3rd
A
C The R–X4th
1st and bond polarity decreases from RCl to RI.
A longer and stronger
B
D
B The solubility
2nd and
longer of AgX(s) decreases from AgCl to AgI.
3rdweaker
and
C
C The ionisation
shorter energy of the halogen decreases from Cl to I.
and stronger
D The bond
shorter energy
and of R–X decreases from RCl to RI.
weaker
[W'08 Q23]
24
24
24 A
In possible mechanism
the hydrolysis of the exothermic
of bromoethane hydrolysis
by aqueous of 2-chloro-2-methylpropane
sodium hydroxide, what is theis nature
shown. of the
attacking group and of the leaving group?
CH3 CH3
attacking group slow
leaving group _
© UCLES 2008 CH3 C Cl 9701/01/M/J/08 CH3 C+ + Cl
A electrophile electrophile
B electrophile CH3 nucleophile CH3
C nucleophile electrophile
D nucleophile CH3 nucleophile CH3

_ fast
CH3 C+ + OH CH3 C OH [S'09 Q24]
CH3 CH3
Which diagram represents the reaction profile for this mechanism?
A B C D
energy energy energy energy
C
C sodium
sodium
H H
D
D reagent HO
Tollens’ reagent
Tollens’
cholesterol
25
21
21 Which
Which halogenoalkane
halogenoalkane will
will undergo an SSNN11 reaction
undergo an reaction and
andproduce
produceaayellow
yellowprecipitate
precipitatewhen
when
AgNO33(aq)
AgNO (aq)
Separate is
is added
added
oxidation to
toit? 9
it? are carried out using
reactions different conditions.
22 A
In 1-chlorobutane
A the general formula
1-chlorobutane
● cold, dilute of which KMnO
acidified class 4of compound, is the ratio of hydrogen atoms to carbon
atoms the highest?
B
B 1-iodobutane
1-iodobutane
● hot, concentrated acidified KMnO4
A alcohols
C
C 2-chloro-2-methylpropane
2-chloro-2-methylpropane
Which statements about the products formed are correct?
B aldehydes
D
2-iodo-2-methylpropane
C carboxylic acids acidified KMnO4:

cold, dilute hot, concentrated acidified KMnO4: [S'11 P12 Q21]
number of hydroxy groups number of 6-membered rings
26
22 D halogenoalkanes
22 Which
Which reaction
reaction will
willgive
give2-chloropropane
2-chloropropaneininthe
present thebest
bestyield?
yield?
remaining
A
A propane
propane gas
gaswith
withchlorine
chlorinegas
gasininthe
thepresence
presenceofofultraviolet
ultravioletlight
light
23 Y A 1
and Z are two widely-used selective weed killers.
10
2
B
B B propan-2-ol
propan-2-ol with
withdilute
dilute NaCl(aq)
NaCl (aq)
1 3
28 C
A reaction pathway diagram OCH
is 2CO2H
shown. OCH2CH2OH
propan-2-ol with SOCl
C C propan-2-ol with SOCl
3 22 CH3 2Cl
D
D D propene
propene with
withdilute
dilute HCl(aq)
3HCl (aq) 3
[S'11 P12 Q22]
Cl Cl
27 energy
21 Many different compounds have been used in aerosol sprays, refrigerators and in making foamed
plastics. Y Z
Which compound
reagent willwill cause the
distinguish Y most ozone depletion?
from Z?
A CCl 3F
acidified AgNO3(aq)
reaction pathway
B CH FCHCl
B 2011
Fehling’s
2 F
solution [Turn
© UCLES
© UCLES 2011
9701/12/M/J/11
9701/12/M/J/11 [Turnover
over
Which
C Nareaction
CH does not have such a profile?
3CH2CH2CH3
D N
Na2O
2CO3(aq) NaCN
A CH3CHO + HCN CH3CH(OH)CN
[W'11 P11 Q21]
28 B C2isH5involved
24 What Br + NaOH theC2mechanism
in → H5OH + NaBr
of the reaction between aqueous sodium hydroxide and
1-bromobutane?
C
A (CH3)3CBr
attack by a +nucleophile
NaOH → (CH on a) COH + NaBr
3 3carbon atom with a partial positive charge
B Br
heterolytic bond fission and attack by a nucleophile on a carbocation
© UCLES
C 2011
homolytic bond fission and attack by 9701/11/O/N/11
an electrophile on a carbanion
D + Br2 Br
D homolytic bond fission and attack by a nucleophile on a carbocation
[W'11 P11 Q24]
29
25
29 Use
The of the DataofBooklet
depletion is relevant
the ozone layer intothe
thisupper
question.
atmosphere reduces the Earth’s natural protection
from harmful ultraviolet radiation.
2.76 g of ethanol were mixed with an excess of aqueous acidified potassium dichromate(VI). The
reaction mixture was
Which compound wouldthen boiled
cause underdepletion
the most reflux for oneozone
of the hour.layer?
The organic product was then
collected by distillation.
A CCl 3F B CF4 C CHCl F2 D CH2F2
The yield of product was 75.0 %.

[S'12 P11 Q29]

30 Whichmass
What statement doeswas
of product not collected?
correctly describe the polymer PVC?
A Combustion
1.98 g of PVC waste
B 2.07 g producesCa highly
2.70 gacidic gas. D 4.80 g
B PVC molecules are saturated.
C The empirical formula of PVC is the same as the empirical formula of its monomer.
© UCLES
D 2011
The 9701/11/O/N/11
repeat unit of PVC is –(CHCl CHCl )–. [Turn over

C X and Z only
D Y and Z only
30
27 The presence of halogen in an organic compound may be detected by warming the organic
Which compound would produce a precipitate quickest?
A B C D
Cl F Cl F
Cl Cl Br F
Cl F F I
9

[S'12 P11 Q27]
31
25 When phenacyl chloride, C6H5COCH2Cl, is reacted with aqueous NaOH, the substitution reaction
follows an SN2 mechanism.
Which structure represents a species formed during the reaction?
A B
H OH H
δ+ δ–
C6H5 C C+ C6H5 C C Cl
O H O– H
C to form 1,2-dibromoethane.
22 Bromine reacts with ethene D
What is the correct description of the–organic intermediate in this reaction? –

H H H H
δ– δ– δ–
A It has a negativeHO Ccharge. Cl HO C Cl
δ–
B It is a free radical.
C O C O
C It is a nucleophile.
C6H5 C6H5
D It is an electrophile.
[S'12 P12 Q25]
26
23 Complete combustion of compound X gives carbon dioxide and water only. A sample of X is
mixed with aqueous potassium(V) dichromate and boiled under reflux for one hour. The mixture
is then distilled and the onlychloroethane
© UCLES 2012
organic substance
→ Q present is collected.
→ sodium
9701/11/M/J/12 propanoate [Turn over
The
The organic substance
intermediate, Q, iscollected reacts
hydrolysed withwith sodium
boiling to givesodium
aqueous hydrogen, but doesto not
hydroxide, givereact with
sodium
2,4-dinitrophenylhydrazine
propanoate. reagent and does not react with ethanol in the presence of
concentrated sulfuric acid to give an ester.
Which reagent would produce the intermediate, Q, from chloroethane?
What can be deduced from this information?
A concentrated ammonia solution
A X is a carboxylic acid.
B dilute sulfuric acid
B X is a ketone.
C hydrogen cyanide
C X is an alcohol.
D potassium cyanide
D X is an alkane.
[S'13 P11 Q23]
24 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol.
How should the first step in the mechanism be described?
A by a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane
B by a curly arrow from the Cδ+ atom of 1-bromopropane to the OH– ion
C by a curly arrow from the C–Br bond to the C atom
D by the homolytic fission of the C–Br bond
25 Pentane, C5H12, is reacted with chlorine in the presence of ultraviolet light. A compound R is
C ethanol
22 Bromine
D ethylreacts with ethene to form 1,2-dibromoethane.
ethanoate
What is the correct description of the organic intermediate in this reaction?

33
28 Coniine is the major constituent of the poison ‘oil of hemlock’.
A It has a negative charge.
B It is a free radical.
C It is a nucleophile.
N CH2CH2CH3
D It is an electrophile.
H
coniine
Coniine can be synthesised by reacting ammonia with a dibromo compound, X.
chloroethane → Q → sodium propanoate
NH3 + C8H16Br2 → coniine + 2HBr
The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide, to give sodium
propanoate. X
Which
What isreagent would
the name produce the
of compound X?intermediate, Q, from chloroethane?
A concentrated ammonia solution

1,1-dibromo-2-propylcyclopentane
B dilute sulfuric acid
1,2-dibromo-2-propylcyclopentane
C hydrogen cyanide
1,4-dibromooctane
D potassium cyanide
1,5-dibromooctane
[S'12 P12 Q28]
34
24
29 Aqueous
A commonsodium hydroxide
industrial reacts
solvent is with 1-bromopropane
a mixture to give
of propanone, CHpropan-1-ol.
3COCH3, and pentyl ethanoate
CH3CO2(CH2)4CH3.
How should the first step in the mechanism be described?
Which reagent would have no reaction with this industrial solvent?
A by a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane
A HCl (aq)
B by a curly arrow from the Cδ+ atom of 1-bromopropane to the OH– ion
B HCN(aq) with a little KCN
C by a curly arrow from the C–Br bond to the C atom
C Na(s)
D by the homolytic fission of the C–Br bond
D NaBH4 99 [S'13 P11 Q24]
35
23 Pentane,
25 Aqueous sodium
C5H12, hydroxide
is reactedreacts with
with 2-bromo-2-methylpropane
with chlorine
reacts to
to give
give 2-methylpropan-2-ol.
in the presence of ultraviolet
2-bromo-2-methylpropane light. A compound R is
2-methylpropan-2-ol.
found in the products. R has molecular formula C5H10Cl 2. Each molecule of R contains one chiral
The2012
reaction
carbon
© UCLES SNN11 mechanism.
atom.proceeds by an S mechanism.
9701/12/M/J/12
How should
Which the first
two atoms of step in the
the mechanism
the pentane mechanism be described?
bebe
chain could described?
bonded to chlorine atoms in this isomer?
–
– δ+
A byand
1 a curly
3 arrow B
from1aand
lone
lone5 pair
pair on
on the
C OH
the OH ion
2 andion3to
to the Cδ+Datom
the C atom of
of 2-bromopropane
2 and2-bromopropane
4
B by a curly arrow from the C–Br
C–Br bond
bond to
to the
the Br
Br atom
atom
C by a curly arrow from the C–Br
C–Br bond
bond to
to the
the C
C atom
atom
D by the homolytic fission of the
the C–Br
C–Br bond
bond
[S'13 P12 Q23]
36
24 Compound Y can be hydrolysed
hydrolysed by
by warm
warm aqueous
aqueous silver
silver nitrate
nitrate to
to form
form aa precipitate
precipitate that
that isis
soluble in dilute aqueous ammonia.
ammonia. Compound
Compound Y
Y can
can undergo
undergo an
an elimination
elimination reaction
reaction to
to form
form an
an
alkene.
© UCLES 2013 9701/11/M/J/13
What could be the skeletal formula
formula of
of compound
compound Y?
Y?
A B
B C
C D
D
Br II Cl
Cl Cl
Cl
[S'13 P12 Q24]

25 The compound shown is menthol,
menthol, aa naturally-occurring
naturally-occurring alcohol
alcohol found
found in
in peppermint
peppermint oil.
oil.
OH
OH
C ethanolic sodium hydroxide, followed by bromine
C D
D ethanolic sodium hydroxide, followed by hydrogen bromide
37
25 A carbanion is an organic ion in which a carbon atom has a negative charge. A carbocation is an
organic ion in which a carbon atom has a positive charge.
What is involved in the mechanism of the reaction between aqueous sodium hydroxide and
2-bromo-2-methylbutane?
A heterolytic bond fission followed by an attack by an electrophile on a carbanion

B heterolytic bond fission followed by an attack by a nucleophile on a carbocation
29 How many isomeric esters, including structural isomers and stereoisomers, can be made with the
C homolytic
molecular bondCfission
formula followed by an attack by an electrophile on a carbanion
5H10O2, if methanoic acid is one of the two reactants used?
D homolytic bond fission followed by an attack by a nucleophile on a carbocation

A 2 B 3 C 4 D 5
[S'13 P13 Q25]

26 Which compound gives an organic product with a lower boiling point when it is heated under
38
30 CCl 2FCCl F2 can be converted into CH2FCF3 by the following route.
reflux with an excess of acidified potassium dichromate(VI)?
A step 1
2-methylbutan-1-ol step 2 step 3
CCl 2FCCl F2 CCl 3CF3 CCl 2FCF3 CH2FCF3
B 2-methylbutan-2-ol
What type of reaction is step 1?
C pentan-1-ol
A
D addition
pentan-2-ol
B elimination
27 C
Use isomerisation
of the Data Booklet is relevant to this question.
Which
D volume of oxygen, at room temperature and pressure, is needed for complete combustion
oxidation
of 0.1 mol of ethanol? 13 [S'13 P13 Q30]

3 3 3 3
A 7.2 dm B 8.4 dm C 14.4 dm D 16.8 dm
39
29 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
© UCLES 2013 2-ethyl-3-methylbutanoic
9701/13/M/J/13 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 CH3 CH CH2 CHBr CH3

CH3
B CH3 CH CHBr CH2 CH3
CH3 C 2 H5
C CH3 CH CH CH2Br
CH3 CH2Br
D CH3 CH CH2 CH CH3

[W'09 P11 Q29]
30 The acarid mite releases Iardolure to attract other mites to a host. This chemical can be
destroyed by hydrolysis with acid.
CH3CH2CH2[CH(CH3)CH2]3CH(CH3)O C H
O
A simplified formula for lardolure may be written as follows.
RCH(CH3)O C H
23 C CH2=CHCH2Cl + Br2CCl
Dichlorodifluoromethane, → DBCP 10 in aerosol propellants and as a refrigerant.
2F2, has been used
26D many
In ClCH 2CH=CH
countries
Which statement 2 + PBr
plastic
helps 5 → DBCP
to waste
explainiswhy + PBr3separately and sorted. Some of this is incinerated to
collected
dichlorodifluoromethane is chemically inert?
provide heat for power stations.
A The carbon-fluorine bond energy is large.
24 Why
40 Eachisofpvc,
the polyvinylchloride,
following compounds is effective
removed as awaste
from any refrigerant.
that is to be incinerated?
B The carbon-fluorine bond has a low polarity.
The Itrelease
A of which
destroys one layer.
of these causes the greatest depletion of the ozone layer?
C Fluorine is the ozone
highly electronegative.
A
B CCl not burnBeasily.
2F2 compounds
ItFluorine
does CH 3OCH C CH3CHF2 D CH3CH2CH3
3
D are non-flammable.
C It is easily biodegradable. [W'03 Q24]
25
41 1,1-Dichloropropane
24 D Its identical
Under combustion reactseven
products
conditions, with aqueous
though it sodium
are harmful. hydroxide
proceeds in a series
by the same of stepsreaction
mechanism, to give 1propanal.
is faster
than reaction 2.
NaOH(aq)
27 Polymerisation
reaction 1 of CH CH3CH
1,1-dichloroethene
3CHBrCH CHCl ⎯⎯⎯⎯→
produces
3 + 2NaCN 2
→ CH3high
a dense,
CH3CH(CN)CH CH
3 +2CHO
melting point substance that does
NaBr
not allow gases to pass through. It is used as cling wrapping.
reaction 2 CH3CHBrCH3 + NaI → CH3CHICH3 + NaBr
What is the mechanism of the first step of this reaction?
Which sequence appears in a short length of the polymer chain?
What factor will explain this result?
A [ CH2CCl2CH2CCl2CH2CCl2 ]
B elimination
A The C I bond is a stronger bond than the C Br bond.
B [ CHClCHClCHClCHClCHClCHCl ]
C
B Thenucleophilic
C substitution
N bond is a stronger bond than the C I bond.
C [The
C CClcyanide
2CCl2CCl 2CCl
is a2CCl ]
2CCl2 nucleophile
D oxidation
ion stronger than the iodide ion.
D
D [The CHcyanide
2CCl2CHClCHClCH 2CClnucleophile
ion is a weaker 2 ] than the iodide ion.

[S'05 Q24]
42
28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form
9701/1/O/N/03
an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration
of OH– ions present. 9
28 Which is the most

reagent likely
could molecular
best be usedstructure of Y? between cyclohexene and cyclohexanol?
to distinguish
+
A CH 3CH32)CH
Ag(NH 2CH
2 in H22O
Br
B Br23in
CH 2CHBrCH
CHCCl 4 3
C (CH 3)2CHCH2Br
2,4-dinitrophenylhydrazine in CH3OH
D (CH3)34
NaBH CBr
in CH3OH
[S'10 P11 Q28]
43
29 Which
29 isomer
Compound X, of C4H10O forms
molecular three
formula C4Halkenes on dehydration?
8, undergoes the following reactions.
A butan-1-ol Br2 aq.NaOH / heat

C4 H8 C4 H8 Br2 C4 H10 O2
B 2005
© UCLES butan-2-ol 9701/01/M/J/05 [Turn over
X Y Z
C 2-methylpropan-1-ol
D 2-methylpropan-2-ol H2 / Ni
C4 H8 methylpropane
X
What is the formula of compound Z?
A CH3CH2CH(OH)CH2OH
B CH3CH(OH)CH(OH)CH3
© UCLES CH3CH(CH2OH)CH2OH
C 2010 9701/11/M/J/10
D (CH3)2C(OH)CH2OH
[W'11 P12 Q29]
30 How many of the isomeric alcohols with the formula C4H9OH will produce an alkene that has cis
and trans isomers, on treatment with conc. H2SO4?
A 1 B 2 C 3 D 4

C CH3 CH=CH2 + H2 O ⎯⎯⎯→ CH3 CH(OH)CH3
D CH
What willCHO + HCN
be formed
3 ⎯→
when ‘leafCH CH(OH)CN
alcohol’
3
is oxidised using an excess of hot, acidified K2Cr2O7(aq)?
A CH3CH2CH(OH)CH(OH)CH2CO2H
26 B
44 The CH
reaction scheme2CO
3CH2COCOCH outlines
2H the production of one of the monomers of nylon 66 from
compound X. 8
C CH3CH2CH=CHCH2CO2H
KCN reduction
compound X and HO CCH NCCH 2 CH2 CH2 CH2 CN H N(CH ) NH
21 D
21 Including
CH
Including structural
3CH 2CO2H and
structural in ethanol
and CO
stereoisomers,
2 2 2 Hhow many isomers are there of C222H22Br22?2 6 2
A 22
A B 3 C 4 D 5
Which compound
23 Which compound exhibits X?
could bestereoisomerism?
22 A
22 A BrCH
CH
Which
Which 2 CHCH
3CHCl
reaction
reaction2 CH
will
will CH2 Br
3 2 give
give the best yield of 2-chloropropane?
B
B
A CH =CHCH=CH
CH32CHCl
chlorine Cl 2propane gas in the presence of uv light
CHwith
gas with
2
A chlorine gas
C
C
B HOCH
CH 3CCl2 CH
chlorine CH2 3CH
gas
2gas 2 CH
with 2 OH
propene gas in the dark
B chlorine with
D CCH
HO22Cl CH22CH CH2 CH2 CO2 H
D
C
C CH
propan-2-ol
propan-2-ol CH 2 Cl
with
2
with dilute NaCl (aq)
[S'03 Q26]
D
D propan-2-ol with
propan-2-ol with PCl 55
27
45 Chlorofluoroalkanes,
24 A commonly
carbanion is an organic known
ion in which as CFCs,
a carbon undergo
atom has homolytic
a negative fission
charge. by ultraviolet
A carbocation is an
irradiation
organic ionininthe stratosphere.
which a carbon atom has a positive charge.
23 Pent-2-ene,
23 Pent-2-ene, CH CH22CH=CHCH33, reacts in a similar way to ethene.
CH33CH
Which
The radical could
reaction between result from thissodium
aqueous irradiation of CHFClCF
hydroxide 2 Cl ?
and 1-bromobutane proceeds by an SN2
mechanism.
Pent-2-ene is
Pent-2-ene
A CHFCl CFCl
·
is reacted
reacted with cold, dilute, acidified manganate( VII ) ions.
How ·will
Whatshould bethe
will be first step
produced in in
thethe mechanism
greatest be described?
amount?
B CHClCF2 Cl
What produced
· 33CH
C CHFCF 2 Cl
AA attack
CH
CH CHby a nucleophile on a33carbon atom with a partial positive charge
CH(OH)CH(OH)CH
22CH(OH)CH(OH)CH
· 33CH
D
B CFClCF
B heterolytic
CH
CH Cl
CH22COCOCH
2
bond fission
COCOCH 33 followed by an attack by an electrophile on a carbanion
C
C heterolytic
aa mixture bond
mixture of
of CH33fission
CH followed 22by
CH22CH(OH)CH CHan attack
33 and CHby3CH
a nucleophile on a 3carbocation
2CH2CH(OH)CH
28 D
In
D itshomolytic
reaction
CH
CH with
bondsodium,
CH22COOH
33CH COOH fission
and CH 1 3mol
followedof a
3COOH bycompound X gives
an attack by a nucleophile on2 (g).
1 mol of H a carbocation
[W'13 P11 Q24]

Which compound might X be?
46
24 Including
24 Including structural
structural and
and stereoisomers, how many isomeric products are produced when alcoholic
A
KOHCH
KOH 3 CH2 CH2 CH2 OH
reacts
reacts with 2-chlorobutane?
with 2-chlorobutane?
B (CH3 )3 COH
A
A 11 B
B 2 C 3 D 4
C CH3 CH2 CH2 CO2 H [W'13 P13 Q24]
47
© D
25UCLES
25 CH3 CH(OH)CO2 HCFCs, can be 9701/11/O/N/13
Chlorofluorocarbons,
Chlorofluorocarbons,
2013 used as refrigerants, aerosol propellants andover
[Turn fire
extinguishers.
extinguishers.
CFCs such
CFCs such as
as CCl F and CCl 22F22 are more stable than chloroalkanes such as CCl 4.
CCl 33F
What is
What is the
the reason
reason for
for their greater stability?
A
A Fluorine has
Fluorine has aa higher
higher first ionisation energy than chlorine.
B
B Fluorine radicals
Fluorine radicals are more stable than chlorine radicals.
C
C The
The C–F
C–F bond
bond energy
energy is larger than the C–Cl bond energy.
D
D The
The C–F
C–F bond
bond is
is more polar than the C–Cl bond.
9 [W'07 Q25]
48
26 Halogenoalkanes react with aqueous NaOH to give alcohols. The mechanism involved is either
SN1 or SN2.
Which halogenoalkane produces the highest percentage of product by an SN1 mechanism, when
treated with aqueous NaOH?
A 2-bromopropane
© B 2013
© UCLES
UCLES 2-chloropropane
2013 9701/13/O/N/13
9701/13/O/N/13
C 1-iodo-2-methylpropane
[W'13 P13 Q26]

27 An alcohol with molecular formula CnH2n+1OH has a chiral carbon atom but does not react with
hot, acidified K2Cr2O7.
What is the smallest possible value for n ?

11
49
28 Which reaction will give 2-chloropropane in the best yield?
A propane gas with chlorine gas in the presence of ultraviolet light

B propan-2-ol with dilute NaCl (aq)
C propan-2-ol with SOCl 2(l)
D propene with dilute HCl (aq)
[S'11 P12 Q22]
29 The ester, CH3CH2CO2CH3, is hydrolysed by boiling with aqueous sodium hydroxide.
Which compound is one of the products?
A ethanol
B propan-1-ol
C sodium methanoate
D sodium propanoate
30 Caprolactone is a cyclic ester. It is being used increasingly for the manufacture of specialist
polymers.
caprolactone
From which compound could caprolactone be made by a single reaction?
A OHCCH2CH2CH2CH2CHO
B HOCH2CH2CH2CH2CH2CH2OH
C HOCH2CH2CH2CH2CH2CO2H
D HO2CCH2CH2CH2CH2CO2H

be correct.
Decide whether each of the statements is or is not correct (you may find it helpful to put a tick against
the statements that you consider to be correct).13
SECTION B
37
The What will always
responses A to Dbe a characteristic
should be selected ofon
a compound
the basis ofcontaining a single carbon atom with four
different groups bonded to it?
A B 13 C D
1 It will have an optical isomer.
37 2Which sodium
It1, and salts
2 have
will formcentre.
3a chiral a precipitate
1 and 2 when AgNO3(aq) followed
2 and 3 by dilute NH 3(aq) is added to its
1 only
aqueous solution?
are only are only are is
3 It will have a structural isomer.
1 chloride
No 2 bromide
1 other
38 combination
Chloroethane of statements
can be formed fromisbromoethane
used as a correct response.
in two steps.
3 iodide
Use of the Data Booklet may be appropriate
step X for some questions.
step Y
Be
C2H5Br C2H5OH C2H5Cl
38 Which compounds would be formed23in the reaction of ethene with aqueous bromine in the
31 Which
Which statements
statements
presence about
about
of sodium the atoms
these
chloride? steps are and 24Mg are correct?
Nacorrect?
11 They
Step Xhave
CH ClCH the same
involves
Cl numbersubstitution.
a nucleophilic of filled electron orbitals.
2 2
2 They
Hot have
CH2aqueous
BrCH the samehydroxide
sodium number of the reagent in step X.
is neutrons.
2Cl
3 Hot
CH2aqueous
They Br sodium
are 2both
BrCH chloride
reducing is the reagent in step Y.
agents.
[W'12 P12 Q38]
39
2 When
39
32 the apparatus
Halogenoalkanes
Which compounds below
react withwas
contain used with
aqueous
covalent compound
alkali.
bonds? Z, a brick-red
One mechanism precipitate
of this reactionformed in the
has the right-
reaction
hand tube.
pathway diagram shown below.
1 aluminium chloride
air to pump
2 ammonia Z
3 calcium fluoride
Y
energy
33 Ethylene glycol, HOCH2CH2OH, is used as a de-icer. It allows ice to melt at temperatures below
A
0 °C. X
R – Hal + OH –
Which statements are correct? Fehling's reagent
compound Z in
ROH + Hal–
1 acidified
Ethylenepotassium
glycol changes the extensive network of hydrogen bonds in ice.
dichromate(VI)
2 Ethylene glycol molecules form hydrogen
reactionbonds with other ethylene glycol molecules.
pathway
3 Ethylene glycol molecules will dissolve in the water formed from the ice.
Which of the following statements are correct?
heat
1 The reaction is an example of nucleophilic substitution.
2 Between
Which X and
compound Y the
could beC-Hal
Z? bond will be lengthening.
3 The energy difference between X and Z represents the activation energy.
1 CH3CH(OH)CH3 2 CH3CH2CH2OH 3 CH3OH
[S'02 Q39]
40 Which alcohols on oxidation with acidified potassium dichromate(VI) give an organic product
which causes an effervescence when reacted with sodium carbonate?
1 butan-1-ol
2 2-methylpropan-1-ol
3 2-methylpropan-2-ol
9701/1/M/J/02

17
3 When halogenoalkanes, RX, are hydrolysed with NaOH, the corresponding sodium halide, NaX,
38
is produced.
RX + NaOH → ROH + NaX
A student investigated the amount of NaX produced by hydrolysing CH3CH2Cl and another
halogenoalkane, Y. In a given time the amount of sodium halide formed was greater with Y than
with CH3CH2Cl.
A
number of Y
moles of
NaX formed
CH3CH2Cl
14

0
0 time
A B C D
Which compound could be Y?
1, 2 and 3 1 and 2 2 and 3 1 only
1 Cl CHare2CH2Cl
only are only are is
2 CH3CH2Br
3 CH
No other 3CH2I
[W'04 Q38]
4 Pentaerythritol
39
38 Fabrics for useisinan intermediate
aircraft seatingin thetreated
are 13 a coating
manufacture
with of paint.containing a halogenoalkane.
37 Which
Why is equations represent HOCH
used? stages in CHprocess
the Contact OH for manufacturing sulphuric acid?
A
this coating 2 2
C
1 S
The+O 2 → SO
treated fabric
2 HOCH
burns less easily, CH2safety.
improving
2
OH
pentaerythritol
22 H 2O treated
The + SO2 → H2SO
fabric forms
3 hydrogen bonds to water more readily, so it is easier to wash.
1
3Which
H of halogenoalkane
2SO
the following statements
3 + 2 O2 → H2SO
about pentaerythritol are correct?

The undergoes
4 addition polymerisation, stiffening the fabric.
15
1 It reacts with metallic sodium. [S'13 P13 Q38]
5 The
39
37
38 A liquid
For
2 the X is known
following to concentrated
be either aallsingle
three hydrocarbons
It is reaction
dehydrated by occurorganic
acid compound
naturally.
sulphuric or a mixture of organic compounds.
to an alkene.
When treated with sodium, X gives off hydrogen gas.
3 Its of
Which empirical formula
these will is CH3O.two organic –compounds, both containing
be split –
(CHinto
3)3SiCl + C2H5O → (CH3)3SiOC2H5 + Cl
a ketone group, when
A
treated with hot acidified potassium manganate(VII)?
When treated with 2,4-dinitrophenylhydrazine reagent, X gives orange crystals.
which statements are likely to be true?
Which deductions about X can definitely be made?
1 It involves nucleophilic attack by C2H5O–.
2
11 At –least one component 3
of X is a carbonyl compound.
2 Cl is displaced by C2H5O–.
2 Only one of the components of X is a carbonyl compound.
3 The oxygen-carbon bond is not broken.
3 At least one component of X is an alcohol.
[W'05 Q38]
39 Modern cars are fitted with catalytic converters. These remove carbon monoxide, unburnt
6 Which
38 hydrocarbons
areacid, and
CH3oxides
properties of H, of an
nitrogen
fluoroalkanes? fromchemical
exhaust which
gases.is used in the industrial manufacture of
A
40 Ethanoic CO 2 is important
rayon
1 andare
They aspirin.
less reactivegases
than the
Which
© UCLES 2004
of these pollutant arecorresponding
removed chloroalkanes.
by oxidation?
Which processes
2 can be used to make ethanoic acid?
1 They
carbonaremonoxide
non-flammable.
31
2 The C-F bond
hydrolysis is stronger than a C-Cl bond.
of ethanenitrile
hydrocarbons
[S'13 P12 Q37]

32 nitrogen
oxidationoxides
of ethanol
39 Which compounds are able to react with concentrated sulphuric acid to give a product that will
3 oxidation of ethanal
decolourise acidic potassium manganate(VII)?
40 The sex-attractant of the house-fly is muscalure, with the following formula.
1 (CH3)3COH
CEDAR
2 COLLEGE
CH3CH2CH(OH)CH3 CH3(CH2)7CH =305
CH(CH2)12CH3 HALOGENOALKANES WS 3
3Which 3CO2H
CHstatements about muscalure are correct?
7 Deuterium, D, is the 1H isotope of hydrogen. 13

2
38 DBr has the same chemical properties as HBr.
Which compounds could be made by the reaction

Section B of DBr with another compound in a single
reaction?
be correct. Br
D
1 whether each of the statements is or is not correct (you may find it helpful to put a tick against
Decide
the statements that you consider to be correct).
A B
15
15 C D
B
2 CHBr2CHDBr
34 Why does a mixture of hydrogen gas and bromine gas react together faster at a temperature of
34 Why does a mixture
3 at aoftemperature
hydrogen
1 and 2gas and bromine gas react together1 faster
only at a temperature of
500 K 1, 2 and
than it does of 400 K? 2 and 3
500 K than
areit does at a temperature
only are of 400 K? only are is
correct OD correct correct correct
1 A higher proportion of effective collisions occurs at 500 K.
13 ACH higher proportion of effective collisions occurs at 500 K.
3CH
2 Hydrogen molecules and bromine molecules collide more frequently at 500 K.
Brmolecules

2 Hydrogen
No other combination and bromine
of statements is used molecules collide
as a correct more frequently at 500 K.
response.
3 The activation energy of the reaction is lower at 500 K.
14 at [S'06 Q38]
3 The activation energy of the reaction is lower 500 K.
8 responses A to D should be selected on the basis of
•
39 The
31 How chlorine
can the rate of reaction
oxide between
free radical, ClOethanal and aqueous
, is formed hydrogen
during the cyanide
depletion be increased?
of the ozone layer by
The
35 chlorofluoroalkanes (CFCs).
35 AA farmer added
1 farmer added lime
by irradiation lime
with
to damp soil,
to damp
ultraviolet
soil, followed
light
followed by
by the
the nitrogenous
nitrogenous fertiliser
fertiliserammonium
ammoniumsulfate.
sulfate.AA
chemical reaction occurred in the
chemical reaction occurred in the soil.• soil.
•
2 by a rise A in temperature B Cl + O3 → ClO + C O2 D
Which substances were formed in this
Which substances were formed in this reaction? reaction?
Which
3 by1,features
the 3are present
addition
2 and of a smallin1quantity
the
andchlorine oxide free
2 of aqueous 2 radical?
sodium
and 3cyanide 1 only
11 sulfuric acid
sulfuric acid
1 an odd number of electrons
40 22Which
calcium sulfate
statements
calcium sulfateabout lactic acid, CH3CH(OH)CO2H, are correct?
2 a single covalent bond
331 ammonia
ammonia
Lactic acid forms opticalfrom
isomers.
3 a
No other dative covalent
combination bond
of statements oxygen
is usedtoaschlorine
a correct response.
2 Two hydrogen atoms per lactic acid molecule can be involved in hydrogen bonding. [W'06 Q31]
36
36 Which
Which statements
statements about
about the reaction
thebehaves
reaction of solid
ofwhen sodium bromide with concentrated sulfuric acid are
9
32
38 Concentrated
3 Lactic
What ofsulphuric
typesacid would acid
form
reaction arean aldehyde
undergone as asolid
by
sodium
strong
oxidised bromide
acid when withpotassium
it reacts
by acidified
2-bromopropane?
concentrated
with water. sulfuric acid are
dichromate(VI).
correct?
correct?
A
111 Hydrogen
elimination
Hydrogen bromide is a
bromide is H2SO4(l)of
a product
product + the
of aq →
the H+(aq) + HSO −4 (aq)
reaction.
reaction.
222 Sulfuric
free radical
acid substitution
is oxidised to sulfur dioxide.
dioxide.
The Sulfuric
HSO −4 ion formed behavessulfur
as a weak acid.
333 Bromide

nucleophilic
Bromide ionssubstitution
are reduced to bromine.
bromine.
HSO −4 (aq) H+(aq) + SO 24− (aq) [S'07 Q38]
10
39
© UCLES
37
37 2006statements
Menthol,
Which
Which from oil of
statements are
aremint,
trueis
true forused
for Sin
an mol
1.0 S N2
N
9701/01/M/J/06
–3
2soaps and perfumes.
reaction?
reaction?
dm sulphuric acid?
11 One
One
[H + bond is broken
bond
(aq)] is high another bond
as another isCH
bond is 3
formed.
formed.
A
22
2 The
[The 2formation
SO formation
− of a transition state
4 (aq)] is high
CH the
state involves
involves the collision
collisionofoftwo
twomolecules
moleculesororions.
ions.
33 A
A carbon
carbon atom in the transition stateCH
transition state is CH2 either
is2bonded,
bonded, eitherfully
fullyor
orpartially,
partially,totofive
fiveother atoms.
otheratoms.
3 [ HSO −4 (aq)] = [ SO 24− (aq)]
[W'09 P12 Q36]
CH2 CH(OH)
11 The
38
38 The chlorine
chlorine free radical takes partpart in
in the CH
the destruction
destruction of
ofthe
theozone
ozonelayer.
layer.
C
Which statements
Which statements about this free radical areCH
radical are correct?
correct?
11 ItIt is
is formed fissionCH
formed by the heterolytic fission of 3
of the
theCH 3
covalent
covalent bond
bondininaachlorine-containing
chlorine-containingmolecule.
molecule.
22 ItIt has
has aa single unpaired electron.
electron. menthol
33Which
ItIt has
has the
the same electron arrangement
arrangement as
as aa chlorine
chlorineatom.
atom.
statements about menthol are correct?
[W'09 P12 Q37]
1 There is a total of two chiral centres present in the menthol molecule.
2 On reaction with concentrated sulphuric acid, menthol produces a mixture of two alkenes.
3 A solution of acidified potassium dichromate(VI), on warming with menthol, changes colour
CEDAR COLLEGE
from orange to green. 306 HALOGENOALKANES WS 3
2 (CH3)3CCH2CH2CH3 16
CH3CH2A
The3responses to2C(CH
CH 3)3 be selected on the basis of
D should
12 Which reactions
39 A are examples ofBnucleophilic substitution?
C D
A
1,3CH
2 and 3 – 1 and 2 – 2 and 3 1 only
1 CH 2Br + OH → CH3CH2OH + Br
correct H+ correct correct correct
2 CH3I + H2O ⎯⎯⎯ → CH3OH + HI 14
3CHA
2CH 2Cl NH3be CH3CH 2on 2as a2 +correct
No 3responses
TheotherCH
combination
to D + statements
of
should →selected CHthe
is used NHbasis HCl
of response.
[S'10 P11 Q39]
A B C D
13
40
40 The diagrampathway
A reaction shows some laboratory
diagram apparatus.
is shown.
1, 2 and 3 1 and 2 2 and 3 1 only

energy
38 DHA is a colourless liquid which reacts with protein in skin to cause it to darken. It has the
structure shown.
O
reaction
15 pathway
HOCH2 CCH2 OH
38 Which
Which alkenes,
reactionsonwould
reaction
havewith steam
such at 600 K and
a profile? water
6 x 106 Pa pressure in the presence of a
D
phosphoric acid catalyst, could produce an alcohol DHA containing a chiral carbon atom?
1 (CH3)3CBr + NaOH → (CH3)3COH + NaBr
1 (CH3)2C=CH2
Which observations would be heatmade when testing12 this substance?
2 CH3CH2Br + NaOH → CH3CH2OH + NaBr
2 CH3CH=CHCH3
1 Hydrogen
The Which
responses A toisDproduced
preparations should when
couldbethis sodium
selected isbe
on the
apparatus added.
basis
usedoffor?
33 CH
(CHCH 3)3CCH 2CH2Cl + 2NH3 → (CH3)3CCH2CH2NH2 + NH4Cl

3 2CH=CH2
2 A coloured precipitate is produced when 2,4-dinitrophenylhydrazine reagent is added.
1 bromoethane,
A from ethanol, B sodium bromide and C concentrated sulfuric
D acid [W'10 P12 Q40]
3 A silver precipitate is produced when Tollens’ reagent is added.
14
39 2Bromoethane
ethanal,
1, 2 andfrom ethanol,
undergoes
3 allsodium
1ofand dichromate(VI)
the2conversions and
shown.
2 and 3 sulfuric acid 1 only
3 1,2-dibromoethane,
correct
from bromine and ethene
correctof nucleophilic correct correct
39 Which
On acidconversions are examples substitution?
A
hydrolysis, which compounds produce propanoic acid?
1 C2H3CH 5Br 2→
COC2CH
2H53CN
No other CH
© UCLES
2 2010
C
CH2H 5Br 2→
3CH CHC2CN
2H5OH 9701/11/M/J/10
37 Compound
3 C CH2H3CH X
CHhas
5Br 2→ 2H5molecular
C2Cl NH2 formula C4H10O. Separate samples of X are tested with three

different reagents.
[S'11 P11 Q39]
15
40 Which
X is anresults
Sorbitol could
organic not
compound.
is an artificial be obtained?
X gives
sweetener a to
used precipitate
sweeten with aqueous
chocolate silver
which nitrate. for
is suitable Some or all of this
diabetics.
precipitate remains undissolved when an excess of dilute aqueous ammonia is added.
OH
2,4-dinitrophenylhydrazine warm acidified potassium
Tollens’
What could reagent
be the identity of X? reagent dichromate(VI) solution
H C H
:
1 1 2-chlorobutane
silver mirror forms orange precipitate forms colour changes from orange to green
H C OH
2 2 2-bromobutane
no change no change no change
HO C H
3 3 iodomethane
no change no change colour changes from orange to green
Permission to reproduce items where third-party owned material H C by OH

protected copyright is included has been sought and cleared where[W'11 P13 Q37]
possible. Every
reasonable effort has been made by the publisher (UCLES) to trace copyright holders, but if any items requiring clearance have unwittingly been included, the
16 H C with OHaqueous silver nitrate. All of this precipitate

publisher will be pleased to make amends at the earliest possible opportunity.
38 Y is an organic compound. Y gives a precipitate
dissolves
University when
of Cambridge concentrated
International aqueous
Examinations ammonia
is part of the Cambridgeis added. Group. Cambridge Assessment is the brand name of University of
Assessment
H C H
Cambridge Local Examinations Syndicate (UCLES), which is itself a department of the University of Cambridge.
What
© UCLES is a
2010 possible identity for Y? 9701/12/O/N/10
OH
1 1-bromopropane
sorbitol
2 chloroethane
Which functional groups can be produced when this molecule is subjected to oxidation under
suitable
© UCLES 2011 conditions? 9701/11/O/N/11

[W'11 P12 Q38]

1 aldehyde
39 Which compounds will produce ethanoic acid when boiled under reflux with dilute alkali followed
CEDAR
2 COLLEGE
by acidification?
carboxylic acid 307 HALOGENOALKANES WS 3
3
1 ketone
CH 3CH2Cl
H2(g) + X2(g) 2HX(g) equilibrium constant, Kp
No other combination of statements
+
is used
–
as a correct response.
X(g) → X (g) + e 1411 ionisation energy,
17
The How
40 responses
Which
can aA to Dyield
statements
good should
about be selected
of the on made
relative be
ethylamine the
values basis
of of
these
using
Section quantities are as
B bromoethane correct?
starting material?
1 by
For each
be correct.
2 by K1,
for
the
p for
HClbromoethane
ofheating >
A questions
HBr3dilute
adding > Kp for
infor HBr
this
HI 1 and
aqueous
with
B an excess
section,
ammonia
one or of ammonia
more Cof the gas
to bromoethane
threein numbered
a sealed D tube
statements 1 to 3 may
D
2 and 2 2 and 3 at room temperature
1 only
Decide are
whether each of the only are
statements is or is not only are
correct (you may find it is
helpful to put a tick against

3 by heating
for I >bromoethane
for Cl under reflux with aqueous ammonium chloride
correct
the statements that you considercorrect
to be correct). correct correct
[S'12 P13 Q39]
The responses A to Dofshould be selected on the basis
in of
18
37 Chloroethane
No other can
combination bestatements
formed from bromoethane
is used as a correct two steps.
response.
A B step X step
C Y D
34 C2H5Br
If N2O4 gas is placed in a sealed vessel the Cfollowing
2H5OH equilibrium
C2H5isClestablished.
A
1, 2 and 3 1 and 2 2 and 3 1 only
are
Which statements onlysteps
about these areN2are only2are
correct?2NO
O4(g) (g) is
1
The Hot aqueous
forward sodium
reaction hydroxide is the reagent in step X.
is endothermic.
No other
2 combination of statements
in stepisY.used as a correct response.
WhatSOCl 2 is the
happens reagent
when the temperature is increased?
3 Step X is a substitution reaction.
1 The equilibrium constant increases.
31 Use of the Data Booklet is relevant to this question. [W'12 P13 Q37]
2 The partial pressure of NO2 increases.
19
38 Free-radicals
Which pairs ofplayreagents will react
an important together
part in a redox
in reactions reaction?
involving the destruction of the ozone layer and
3 The activation energy is unchanged.
the substitution of alkanes by chlorine.
1 CH3CHO + Fehling’s reagent
Some CHfree-radicals contain two unpaired electrons. Such species are called diradicals.
35 2
Which 4 + Clof
types 2 bonding are present in ammonium carbonate, (NH4)2CO3?
Which
3 species
3COCH3are diradicals?
1 CH
ionic + Tollens’ reagent
12 Ocovalent
39 An organic compound, X, will react with calcium metal to produce a salt with the empirical formula
23 Cl
D
CaCco-ordinate
4H4O4.
(dative covalent)
3 CH3
What could be the identity of X?
13
36 Sulfur dioxide and sulfites are used in food preservation. [S'13 P11 Q31]
1 ethanoic acid have higher melting points than the Group I metals.
20
32
38 The
Why Group
Whichareof they
theII following
metals would
used for this be suitable for use in a fire extinguisher?
purpose?
2 butanedioic acid
:
Which
1 They
CBrFfactors could contribute
3are reducing towards
agents which the
slow higher
down themelting points?
oxidation of food.
3 2-methylpropanedioic acid
© UCLES 2012 9701/11/M/J/12
CH3(CH
12 There
They are2)5CH
inhibit 2Br
smaller
the interatomic
growth distances
of aerobic in the metallic lattices of the Group II metals.
bacteria.
23 HCl react
More
They electrons are2(g)
with NO available fromit each
converting Group II metal atom for bonding the atom into the
to NO(g).
metallic lattice. [W'08 Q38]
21
39 3
37 The Group II metals
organic
During have
compound
the bromination ofXamethane,
higherafirst
gives theionisation
precipitate energy
when
free radical • than the
warmed
CH withcorresponding Group
aqueous silver I metal.
nitrate. This
3 is generated and a possible terminating
precipitate
step of thisdissolves
reaction iswhen concentrated
the formation of Caqueous ammonia is added.
2H6 by the combination of two free radicals.
33 Valence
What
© UCLES is
2012 ashell electron
possible pairfor
identity repulsion
X? theory should be used to answer this question.
What could be produced in a terminating step during the bromination of propane?
Which species are trigonal planar?
1 1-bromopropane
CH3
11 BH
2 CH3 CH CH CHCH
2-chlorobutane
3 2 2 3
+
23 2-iodo,2-methylpropane
CH 3 CH
3
CH [W'13 P11 Q37]
3 PH3 3
2 CH3CHCHCH3
© UCLES 2013 CH3 9701/11/O/N/13
3 CH3CH2CHCH2CH3
40 The structure of the antioxidant vitamin C is shown in the diagram.
HO OH
C C
CEDAR COLLEGE O C 308

CHCH(OH)CH 2OH HALOGENOALKANES WS 3
O
[3]
[Total : 11]
SECTION A
16 Chlorofluorocarbons, CFCs, are small alkane molecules in which some of the hydrogen
atoms have been replaced by atoms of chlorine and fluorine.
(a) (i) State two uses of CFCs.
...................................................................................................................................
...................................................................................................................................
(ii) What property of CFCs causes them to be useful?
...................................................................................................................................
[2]
(b) A typical CFC is CHF2CHClF.
(i) Which covalent bond in this CFC is the weakest?
...................................................................................................................................
(ii) Why does this CFC present an environmental concern?
...................................................................................................................................
11 For
Examiner’s
Use
...................................................................................................................................
(c) Another CFC contains the following elements by mass. The value of its M r is 135.
...................................................................................................................................
C, 17.8%; H, 1.5%; Cl , 52.6%; F, 28.1%
...................................................................................................................................
Use these data to determine the molecular formula of the CFC.
[3]
11 For
Examiner’s
9701/2/M/J/02 Use
(c) Another CFC contains the following elements by mass. The value of its M r is 135.
C, 17.8%; H, 1.5%; Cl , 52.6%; F, 28.1%
Use these data to determine the molecular formula of the CFC.
C A Cl F
÷
' ' a
Easts Ha
1.5 1.48 1.48

I -
48
o
: CHU F Ll ) mom a
67.5 =
margin [3]
CzHzU2 FL [Total : 8]
[S'02 Q6]
[3]
[Total : 8]

Primary
10 For
Examiner’s
/
Use
25 alkene
CH3
Halogens
CH3 C Br
CH3 CH2CH2CH2Br CH3
1-bromobutane 2-bromo-2-methylpropane
(a) 1-Bromobutane reacts with aqueous sodium hydroxide to form butan-1-ol.
(i) Give a balanced equation for this reaction.

bHzUHzUHzCHz OH Na Br
CHgUHz0HzCHzM t NaOH →
...................................................................................................................................
t
(ii) Name the type of reaction. ........................................................................................
(iii) Describe the mechanism of this reaction.
It H It
.it?itq-sxo--..!q
.
I a
Ho
•
nm me
. .
-
-
c
*
'
I mr Ho
cat
CzH7 ,
It CzH7
[5]
(b) 1-Bromobutane and 2-bromo-2-methylpropane both react with an ethanolic (alcoholic)

solution of sodium hydroxide to form alkenes.
(i) Elimination
Name the type of reaction. ........................................................................................
(ii) Identify, by means of the structural formula, the alkene formed from
I 1-bromobutane,
CHgCHzCHz=CH2
II 2-bromo-2-methylpropane.
CHz=CKH3 ) Gt3
9701/02/O/N/03

11 For
Examiner’s
Use
(iii) Hot, concentrated manganate(VII) ions break the double bond in alkenes. Each of
the two alkenes in (b)(ii) gives CO2 and H2O from the terminal group, but the rest
of the molecule remains as an organic oxidation product. Suggest the formula of
each of these products.
Utz GHz COOH

from I .........................................................................................................................
CHZCO Utz
from II ........................................................................................................................
[5]
(c) Complete the reaction sequence giving the intermediate, the reagents and the
conditions for the synthesis of 2,2-dimethylpropanoic acid.
Utz
CH3 I
CH3
step step
q
CN
CH3 C Br CHS -
-
CH3 C CO2H
I II
CH3 CHS CH3
KON dissolved in ethanol

Step I: reagent .............................................................................................................
Heat under reflux
conditions .........................................................................................................
Step II: Dil HCl I Nil HzS04

reagent .............................................................................................................
.
.
Heat under reflux

conditions .........................................................................................................
[3]
[Total : 13]
[W'03 Q5]
9701/02/O/N/03

observation ...................................................................................................................[2]
[Total : 11]
35 A number of organic compounds containing the halogens fluorine and/or chlorine are
commercially important because of their chemical inertness.
(a) Name three such compounds, and for each state a use where its inertness is important.
(i) ...................................................................................................................................
...................................................................................................................................
(ii) ...................................................................................................................................
...................................................................................................................................
(iii) ...................................................................................................................................
...............................................................................................................................[6]
(b) Under certain conditions in the upper atmosphere, some of these compounds break
down.
(i) Explain how this happens and what effects this has, in chemical terms.
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
...................................................................................................................................
(ii) Suggest alternative compounds, which do not contain a halogen, for two of the
uses you have given in (a).
...................................................................................................................................
...............................................................................................................................[5]
[Total : 11]
© UCLES 2004 9701/02/M/J/04
[S'04 Q5]

8
44 Compound G, in which R– represents the rest of the molecule, was made for use as a tear For
gas in World War 2. Examiner’s
Use
R C CN
Br
compound G
Compound G was made by the following sequence of reactions.
stage I stage II stage III

R–CH3 R–CH2Cl R–CH2CN R–CHBrCN
(a) (i) For stage I and for stage II, state the reagent(s) and condition(s) used to carry out
each change.
U2
stage I reagent(s) ..................................................................................................
UV
light
condition(s) ................................................................................................
.
NACH or KCN in ethanol

stage II reagent(s) ..................................................................................................
Heat under reflux
condition(s) ................................................................................................
(ii) Suggest the reagent(s) and condition(s) necessary to carry out stage III.
Bk
reagent(s) .................................................................................................................
v.v
Light
condition(s) ...............................................................................................................
.
[6]
© UCLES 2005 9701/02/M/J/05

9
Compound G was not actually used in World War 2 and stocks of it had to be destroyed For
safely. The following sequence of reactions was used in this process. Examiner’s
Use
stage IV stage V
R–CHBrCN R–CHBrCO2H R–CH(OH)CO2H
stage VI
R–CH2CO2H
(b) For stage IV and for stage V state the reagent(s) and condition(s) necessary to bring
about each reaction.
Ail HCl or Ail Hz soy
stage IV reagent(s) .........................................................................................................
. .
Heat under reflux

condition(s) ......................................................................................................
NaOH
can
stage V reagent(s) .........................................................................................................
Heat under reflux
condition(s) ................................................................................................
.
[4]
(c) The full sequence of stages I to VI involves some compounds which contain chiral
centres.
(i) Explain what is meant by the term chiral centre.
..................................................................................................................................
..................................................................................................................................
(ii) Draw displayed formulae for the isomers of one compound in the full sequence of
stages I to VI which you consider to be chiral.
"
¥ "
.
i .
[3]
[Total: 13]
[S'05 Q4]

10
55 Many organic reactions are substitution reactions in which the number of carbon atoms in For
the organic compound is unchanged. Examiner’s
Use
(a) What is meant by the term substitution reaction?
..........................................................................................................................................
......................................................................................................................................[1]
(b) One example of a substitution reaction is the formation of an alcohol from a

halogenoalkane.
(i) Write a balanced equation for the formation of ethanol from bromoethane.
..................................................................................................................................
(ii) State the conditions for this reaction.
..............................................................................................................................[2]
(c) In a few organic reactions, the product contains one more carbon atom than the starting
material.
(i) Write the equation for a reaction in which the organic compound bromoethane,
which contains two carbon atoms, is converted into an organic compound which
contains three carbon atoms.
..................................................................................................................................
(ii) State the conditions for this reaction.
..............................................................................................................................[2]
11
(d) Ethanol may be converted into propanoic acid in a three-stage process which uses ethanol
as the only organic compound.
step I step II step III
C2H5OH K L C2H5CO2H
(i) Give the structural formulae of the intermediate compounds K and L.
K ...............................................................................................................................
L ...............................................................................................................................
(ii) State the reagent(s) used and give the essential condition(s) for step I and for
step III.
step I
reagent(s) .................................................................................................................
condition(s) ...............................................................................................................
step III
reagent(s) .................................................................................................................
© UCLES 2006 9701/02/M/J/06
condition(s) ................................................................................................................
[6]
[Total: 11]
[S'06 Q5]

8
8
64 (a) Complete the following reaction scheme which starts with propene. For
4 (a) Complete
In each thebox,
empty following
write reaction schemeformula
the structural which starts withorganic
of the propene.
compound that would Examiner’s
For
In each
be formed. empty box, write the structural formula of the organic compound that would Examiner’s
Use
be formed. Use
Br2Br KMnO +
CH KMnO4 /H
/H+
3 CH=CH
2 4
CHZCHRNCHZRN CH 2
CH=CH cold, CH3UtC0H)CHz0H
cold,dilute
3 2
dilute
A A B
B
HBr
HBr
CH3CH2CHzBr CH3CHzCHzNHz
CHzCHzUtzlN
KCN
KCN in in or
NH3
NH or
or 3
CHSCHCCNKHZ
aqueous in an excess
aqueous CH3UHMUHb in an excess cHzUHNHdCHz
ethanol
D ethanol C F
D C F
H2SO4 (aq) NaOH(in ethanol)

H2SO 4 (aq)
heat under NaOH(in
heat ethanol)
under
heat under
reflux heatreflux
under
reflux reflux
CHgUtz CHI COOH

CHzCH=UH2
or
CHzCHK0zH7CH3
E G
E G 9 [7]
[7]
(b) Under suitable conditions, compound E will react with compound B. For
Examiner’s
(i) What functional group is produced in this reaction? Use
Esters
............................................................
(ii) How is this reaction carried out in a school or college laboratory?

under reactants
Heat reflux both
..................................................................................................................................
together
with Cmc
Hzsoy
..................................................................................................................................
.
.
[3]
[S'10 P21 Q4]
© UCLES 2010 9701/21/M/J/10 [Total: 10]
© UCLES 2010 9701/21/M/J/10

8
74 Halogenoalkanes have many chemical uses, particularly as intermediates in organic For

reactions. Examiner’s
Use
Three reactions of 1-bromobutane, CH3CH2CH2CH2Br, are shown below.
CH3CH2CH2CH2OH CH3CH2CH2CH2NH2
CH3CH2CH2CH2Br
reaction 3
CH3CH2CH=CH2
(a) For each reaction, state the reagent and solvent used.
reaction 1 reagent ............................................................
solvent .............................................................
solvent .............................................................
solvent ............................................................. [6]
(b) When 1-iodobutane, CH3CH2CH2CH2I, is reacted under the same conditions as those
used in reaction 1, butan-1-ol is formed.
What difference, if any, would there be in the rate of this reaction compared to the
reaction of 1-bromobutane?
Use appropriate data from the Data Booklet to explain your answer.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [3]
© UCLES 2010 9701/21/O/N/10

9
Dichlorodifluoromethane, CCl2F2, is an example of a chlorofluorocarbon (CFC) that was For

formerly used as an aerosol propellant. In September 2007, at the Montreal summit, Examiner’s
approximately 200 countries agreed to phase out the use of CFCs by 2020. Use
(c) State two properties of CFCs that made them suitable as aerosol propellants.
1. .......................................................................................
2. ....................................................................................... [2]
(d) When CFCs are present in the upper atmosphere, homolytic fission takes place in the
presence of ultraviolet light.
(i) What is meant by the term homolytic fission?
..................................................................................................................................
..................................................................................................................................
(ii) Suggest an equation for the homolytic fission of CCl2F2.
.............................................................................................................................. [2]
(e) The most common replacements for CFCs as aerosol propellants are hydrocarbons
such as propane and butane.
Suggest one disadvantage of these compounds as aerosol propellants.
...................................................................................................................................... [1]
[Total:[W'10
14] P21 Q4]

8
84 Although few halogenoalkanes exist naturally, such compounds are important as For
intermediates in organic reactions and as solvents. Examiner’s
Use
The bromoalkane B has the following composition by mass: C, 29.3%; H, 5.7%; Br, 65.0%.
The relative molecular mass of B is 123.
(a) Calculate the molecular formula of B.
[3]
Halogenoalkanes such as bromoethane, C2H5Br, have two different reactions with sodium
hydroxide, NaOH, depending on the conditions used.
(b) (i) When hot aqueous NaOH is used, the C2H5Br is hydrolysed to ethanol, C2H5OH.
Describe the mechanism of this reaction. In your answer, show any relevant
charges, dipoles, lone pairs of electrons and movement of electron pairs by curly
arrows.
© UCLES 2010 9701/23/O/N/10

9
(ii) What will be formed when C2H5Br is reacted with NaOH under different For
conditions? Examiner’s
Use
..................................................................................................................................
(iii) What are the conditions used?
..................................................................................................................................
(iv) What type of reaction is this?
.............................................................................................................................. [7]
When 1,4-dichlorobutane, ClCH2CH2CH2CH2Cl, is reacted with NaOH, two different

reactions can occur, depending on the conditions used.
(c) (i) Draw the displayed formula of the product formed when 1,4-dichlorobutane is
reacted with hot aqueous NaOH as in (b)(i).
(ii) Draw the skeletal formula of the product formed when 1,4-dichlorobutane is reacted
with NaOH in the way you have described in (b)(ii) and (b)(iii).
# [2]
[W'10 P23 Q4]
[Total: 12]

4
92 Halogenoalkanes have been widely used as aerosol propellants, refrigerants and solvents For
for many years. Examiner’s
Use
Fluoroethane, CH3CH2F, has been used as a refrigerant. It may be made by reacting ethene
with hydrogen fluoride.
You are to calculate a value for the C–F bond energy in fluoroethane.
(a) Use relevant bond energies from the Data Booklet, and the equation below to calculate
a value for the bond energy of the C–F bond.
CH2 = CH2(g) + HF(g) CH3CH2F(g) ΔH o = – 73 kJ mol–1
C–F bond energy = .................................... kJ mol–1 [4]
(b) Another halogenoalkane which was used as a refrigerant, and also as an aerosol
propellant, is dichlorodifluoromethane, CCl2F2.
State two reasons why compounds such as CH3CH2F and CCl2F2 have been used as
aerosol propellants and refrigerants.
..........................................................................................................................................
..................................................................................................................................... [2]
© UCLES 2011 9701/22/M/J/11

5
CCl2F2 is one of many chlorofluorocarbon compounds responsible for damage to the ozone For
layer in the stratosphere. Examiner’s
Use
(c) By using relevant data from the Data Booklet, and your answer to (a) suggest why CCl2F2
is responsible for damage to the ozone layer in the stratosphere whereas CH3CH2F is
not.
..........................................................................................................................................
..........................................................................................................................................
..................................................................................................................................... [2]
Both CH3CH2F and CCl2F2 are greenhouse gases.
The ‘enhanced greenhouse effect’ is of great concern to the international community.
(d) (i) What is meant by the term enhanced greenhouse effect?
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) Water vapour is the most abundant greenhouse gas.
What is the second most abundant greenhouse gas?
........................................ [3]
A greenhouse gas which is present in very small amounts in the atmosphere is sulfur
hexafluoride, SF6, which is used in high voltage electrical switchgear.
(e) What shape is the SF6 molecule?
................................................... [1]
[Total: [S'11
12] P22 Q2]

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C CH3CO2H + CH3CH2CHCH2OH

Which mass of this product is formed? [S'14 P11 Q23]

D sodium methanoate and ethanol

D Both3)products – form hydrogen bonds with water.

[S'14 P12 Q25]

26 Compound X, C4H8O, produces an orange precipitate when it is reacted with

What could be compound X?

© UCLES 2014 9701/12/M/J/14

Which statement helps to explain why dichlorodifluoromethane is chemically inert?

A All fluorine compounds are non-flammable.

9 [S'14 P12 Q27]

A CH3CH2CO2CO2CH2CH3 [W'14 P13 Q23]

[S'15 P11 Q24]

25 2-bromopropane reacts with a hot concentrated solution of sodium hydroxide in ethanol.

Which substance is the major product of this reaction?

[S'15 P11 Q26]

© UCLES 2015 reagents

Which halogenoalkane would produce compound X?

CEDAR COLLEGE OCH2 CH263

Which compounds are produced when P is hydrolysed using hydrochloric acid?

CH3CH2CH2CH2CH2I + OH– → CH3CH2CH2CH2CH2OH + I–

change in condition reason

12 [S'16 P11 Q25]

© UCLES 2016 9701/11/M/J/16

Which point in the diagram is correctly identified?

[S'15 P13 Q28]

H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq)

H2O(l) + R–X(l) + Ag+(aq) → R–OH(aq) + AgX(s) + H+(aq)

A The bond energy of R–X decreases from RCl to RI.

B The first ionisation energy of the halogen decreases from Cl to I.

C The solubility of AgX(s) decreases from AgCl to AgI.

D The R–X bond polarity decreases from RCl to RI.

99 [S'15 P13 Q29]

[W'15 P13 Q24]

[W'15 P13 Q25]

A CCl F CF4 C CO2 D SO2

What is J? CH3 CH3

B CH3 CH CH2 CH3

The four reactions that follow are all exothermic.

B CH3 C H CH3 C OH CH3 C H [S'16 P13 Q28]

21 CH3 CH3 CH2OH

[S'16 P13 Q27]

A Both reactions involve homolytic bond fission.

2CO(g) + 2NO(g) → 2CO2(g) + N2(g)

A They are chain isomers of each other. OH

B They are geometrical isomers of each other.

[S'17 P12 Q23]

[S'17 P12 Q26]

Which row about the observations made for bromoethane is correct?

colour of precipitate rate of reaction

A cream faster than for iodoethane

[W'17 P12 Q25]

CEDAR COLLEGE 267 HALOGENOALKANES WS 1

© UCLES 2017 9701/12/O/N/17

methanol reacts with an excess of sodium? [W'17 P13 Q24]

26 Compound X produces stage

fructose [M'18 P12 Q21]

[M'18 P12 Q27]

[S'18 P11 Q22]

CEDAR COLLEGE 268 HALOGENOALKANES WS 1

23 Primary halogenoalkanes undergo hydrolysis reactions.

A C2H5Br with H2O

[S'18 P12 Q24]

CEDAR COLLEGE Cl F 269 I HALOGENOALKANES