35 Compared with the HCl molecule, the bond ……X…… of the HBr molecule is ……Y……
Which pairs of words correctly complete the above sentence?
csonn_topical_MCQs
X
Y
4
38) Nov11.12/9
1
9
energy
less
The use of sucrose in food processing depends in part on osmotic pressure, symbol Π.
2
polarity
less
In dilute solution, Π varies with concentration in a similar way to gas behaviour.
3 equation Πlength
greater
V = nRT can be used,
where n is the number of moles of solute molecules
The
contained in volume V at temperature T. The number of moles of solvent molecules should be
ignored.
36 Which statements are true about the Haber process for the manufacture of ammonia?
Under aqueous acidic conditions sucrose is hydrolysed.
1
At higher
temperatures, the yield goes down but the rate of production of ammonia is faster.
C H O + H O → CH OH(CHOH) CHO + CH OH(CHOH) COCH OH
2
At higher sucrose
pressures, the yieldglucose
goes down but the rate fructose
of production of ammonia is faster.
12
22
11
2
2
4
2
3
2
3WhatIncan
thebepresence
of a this
catalyst,
the equation?
yield goes down but the rate of production of ammonia is
deduced from
hydrolysis
faster.
the osmotic pressure
glucose and fructose are
decreases
optical isomers
A
37 Which compounds can be obtained from propene in a single reaction?
B
decreases
structural
8 isomers
1 CH2OHCHOHCH3
C
increases
optical isomers
21 An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers.
2 D ( CH2CH(CH
3) ) n
increases
structural isomers
What is R ?
3 CH2BrCH2CH2Br
AHess’s
H Law can be used
B Cl
CH3 C-H bond energy
D C2in
H5methane.
10 39)
to calculate the C
average
June12.12/38
38 What are the= same
forenthalpy
a pair ofchange
opticalofisomers?
standard
atomisation
22 Menthol is an important compound extracted from the peppermint plant.
= standard
enthalpy change of formation
1 their empirical
formula
CH3
= standard enthalpy change of combustion
2
their functional groups
data values are needed in order to perform the calculation?
3Which
their
structural formula
A
(C),
(H),
OH
(CH4)
8
(H2about
),
(CHphotochemical
B Nov12.11/21
(C),
4)
39 40)
Which
statements
the
chlorination of ethane are correct?
H 3C
CH3
21 An
has the(H
formula
CH
CH2CH3 and
does not possess cis-trans isomers.
3CH=CR
C alkene(C),
(CH
2),
4)
1
Hydrogen gas is one of the products.
D
? 4) only, as
What
is R(CH
2
(C), and
menthol
(H
2), are defined as zero
A propagation step in the mechanism is C2H6 + Cl • → C2H5• + HCl.
How
many chiral centres
A H
B are
Cl there in one molecule
C CH3 of menthol? D C2H5
11 3The amount
of titanium
an ore canfission
be determined
by using the following reaction.
The initiation
stepdioxide
is theinhomolytic
of chlorine.
A 1
B 2
C 3
D 4
+ 2Br
3TiO2 + 4BrF
3 → 3TiF
4 the
2 + 3O2 plant.
22 41)
Menthol
is an important compound
extracted
from
peppermint
Nov12.11/23
23UCLES
The
cracking
of increases
a single hydrocarbon
molecule,
CnH
2n+2, produces
Which
element
in oxidation number
in
this
reaction?
©
2012
9701/12/M/J/12
two hydrocarbon molecules [Turn over
CH3number of carbon atoms in one molecule.
only. Each hydrocarbon product contains the same
Each
hydrocarbon product has non-cyclic structural isomers.
A bromine
B fluorine
What
is the value of n?
AC 4oxygen
D
B
6
C
OH
8
D
9
titanium
H 3C
CH3
24 But-2-ene-1,4-diol is converted in two steps through an intermediate X into ketobutanedioic acid.
© UCLES 2011
menthol
hot acidified KMnO4
9701/12/O/N/11
HOCHchiral
CH=CHCH
OH
X
HO2CCOCH2CO2H
2
2 are there in one molecule of menthol?
How many
centres
step 1
step 2
but-2-ene-1,4-diol
ketobutanedioic acid
A 1
B 2
C 3
D 4
What could be the reagent for step 1 and the intermediate X?
23 The cracking of a single hydrocarbon molecule, CnH2n+2, produces two hydrocarbon molecules
reagent for product
step 1 contains the same number
X
221
of carbon atoms in one molecule.
only. Each hydrocarbon
Each hydrocarbon product has non-cyclic structural isomers.
A
cold acidified KMnO4
HOCH2CH2CH(OH)CH2OH
What
of n? KMnO4
B is the value
hot acidified
OHCCH(OH)CH2CHO
8
21 An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers.
7
csonn_topical_MCQs
What is R ?
18 Sulfur trioxide is manufactured from sulfur dioxide and oxygen, using the Contact process.
A
H
B
Cl
C
CH
73
D
C 2H 5
Which
condition affects the value of the equilibrium constant, Kc?
42)
Nov12.11/22
18 Sulfur trioxide is manufactured from sulfur dioxide and oxygen, using the Contact process.
22 Menthol
is an important
compound extracted from the peppermint plant.
A adjusting
the temperature
Which condition affects the value of the equilibrium constant, Kc?
CH3
B increasing the pressure
A adjusting the temperature
removing SO3 from the equilibrium mixture
C
B
increasing the pressure
D C using
a catalyst
removing
SO3 from the equilibrium mixture
D
OH
using a catalyst
19 Which reagent, when mixed and heated
ammonium
sulfate, liberates ammonia?
H3C with CH
3
19 Which reagent, when mixed and heated with 10
ammonium sulfate, liberates ammonia?
A aqueous bromine
menthol
10
A aqueous
29 Synthetic
resins,bromine
plasticisers and many other
10 chemicals can be made by polymerisation of a
B
dilute hydrochloric acid
How
many
chiral centres
are there
in one molecule
of menthol?
variety
of monomers
including
prop-2-en-1-ol,
CH2=CHCH
2OH.
29 Synthetic
resins,
plasticisers
B dilute
hydrochloric
acid and many other chemicals can be made by polymerisation of a
29 variety
Synthetic
resins, plasticisers
and
many otherCH
chemicals
can
be made by polymerisation of a
C
limewater
=CHCH
of
monomers
including
prop-2-en-1-ol,
2
2OH.
A
Bincluding
2 theprop-2-en-1-ol,
C in 3CH
D 4
Which
represents
repeat unit
poly(prop-2-en-1-ol)?
variety
of
monomers
2=CHCH2OH.
C1 structure
limewater
) in acidic
D potassium
dichromate(
Which
structure represents
theVI
repeat
unit insolution
poly(prop-2-en-1-ol)?
) in acidic
potassium
dichromate(
A D structure
CH
CHrepresents
CH2 OH
Which
theVIrepeat
unitsolution
in poly(prop-2-en-1-ol)?
2
23 43)
The June13.11/20
cracking of a single hydrocarbon molecule, CnH2n+2, produces two hydrocarbon molecules
A
CH CH CH2 OH
only.
Each
A
CH22hydrocarbon
CH CH2 product
OH contains the same number of carbon atoms in one molecule.
B
CH
CH
20 20
The
following
compounds
arenon-cyclic
foundin in
the
seaweed
Asparagopsis
taxiformis.
2
The
following
compounds
are
found
the
seaweed
Asparagopsis
taxiformis.
Each
hydrocarbon
product has
structural
isomers.
B
CH2 CH
CH OH
B
CHcompound
CH
Which
could show
isomerism
and optical
isomerism?
Which
showboth
bothcis-trans
cis-trans
isomerism
and optical
isomerism?
What
is compound
the2 value2of could
n?
CH OH
CH22OH
CD C
D
A
B 6
9
A C
BB C 8
D
C 4 A
CH
Br
Cl
Cl
O
C
CH
Cl C H
H Cl
Br
Cl H H
O
C
CH C
Cl
CH
H 2OH
Br
24 But-2-ene-1,4-diol
is
converted
in
two
steps
through
an
intermediate
X
into
ketobutanedioic
acid.
Br
Br
Br
C C
C
C
Br
C CH OH
Br
Br
Br
Br
C C
C
C
Br
C CH22OH
Br
I
Br CH
Cl
C KMnO
C
C
C
C
C
D C CH
C2 CH
hot acidified
2
4
Br
Br
Cl
C C
C
C
C
C
DC HOCH
CH CH2 OH C
CH CH=CHCH
X
HO2CCOCHBr2CO2H H
DBr
CH
CH22 H2CH
Cl
I
H
H
2
OH2
step 1
step 2
Cl
Br
H
I
H
H
H
OH
but-2-ene-1,4-diol
ketobutanedioic
acidBr
OH
in sour milk.
21
Lactic
acid (2-hydroxypropanoic
acid),
CHthat
3CH(OH)CO
2H, is found
30 44)
Some
vegetable
contain
‘trans
fats’
are associated
June13.11/30
What
could
be theoils
reagent
for step
1 and
the intermediate
X? with undesirable increases in the
amount
of cholesterol
in the blood.
30
vegetable
oils contain
contain
‘transacid),
fats’ that
that
are associated
associated
with
undesirable
increasesininthe
the
CH(OH)CO
is found
in sourincreases
milk.
21
Lactic
acid
(2-hydroxypropanoic
CH3are
30 Some
Some
vegetable
oils
‘trans
fats’
undesirable
2H,with
Which
reaction
could occur with
lactic
acid?
amount
of
cholesterol
in
the
blood.
amount of cholesterol
in the
blood.
reagent
X chains.
and 1R2 are different hydrocarbon
In the diagrams
below,for
R1step
+ CHwith
→ CH
A CH
Which
reaction
could2Hoccur
acid?
3CH(OH)CO
3OH lactic
3CH(OCH3)CO2H + H2O
and
R
are
different
hydrocarbon
chains.
In
the
diagrams
below,
R
R224are differentHOCH
hydrocarbon
chains.
InAthe diagrams
R11 and
coldbelow,
acidified
KMnO
2CH2CH(OH)CH
2OH
Which
correctly
illustrates
an
optically
active
‘trans
B diagram
CH3CH(OH)CO
H
+
HCO
H
→
CH
CH(O
CH)CO
H
+ H 2O
2
2
3
2
2 fat’?
→
CH
A
CH
3CH(OH)CO2H + CH3OH
3CH(OCH3)CO2H + H2O
Which
diagram
correctly
illustrates
anoptically
opticallyactive
active‘trans
‘transfat’?
fat’?2CHO
B diagram
hotcorrectly
acidifiedillustrates
KMnO4 an
OHCCH(OH)CH
Which
C CH3CH(OH)CO2A
H + NaHCO3 → CH3CH(ONa)CO2H + H2O +
B CO2
BC CH
→ CH
3CH(OH)CO
2H + HCO
2H
3CH(O
2CH)CO2H + H2O
steam
and concentrated
H
HOCH
2SO4
2CH(OH)CH2CH2OH
A
B
B
D CH3CH(OH)CO2AH + Cl 2
→ CH3CH(Cl )CO2H
+ HOCl
H
H
R
CO
CH
CD CH3CH(OH)CO
H
+
NaHCO
→
CH
CH(ONa)CO
H
+
H2O R+1CO
CO2CH
1
2
2
warm acidified
K2Cr2O7 3
2
3HO2CCH=CHCO
2 2H
2 2
H
H RRCO
R1CO
CO2CH
CH2
COCH
CH2
H
H
R
1
2
1
2
2
1
2
2
CH
C(CH
)7CO
D CH
+ 2Cl
)CO
HOCl2)7CO2CH
3CH(OH)CO
2H
2 2CH → CH3CH(ClCH
2H2)6C + C(CH
3(CH2)6C
3(CH
CH33(CH
(CH22))66C
C C(CH
C(CH22))77CO
CO22CH
CH
CH3(CH
)6C C(CH
C(CH
)7CO
CH
CH
3(CH
2CH
2)26C
2)27CO
2CH
H
H
R1CO2CH2
R2CO2CH2
H
R11CO
CO22CH
CH22
H
HH
R
RR
2CO
2CH
2CO
2CH
2 2
C
C
C
© UCLES 2012
H
H
H
CH3(CH2)6C
(CH22))66C
C
CH33(CH
© UCLES 2013
© UCLES 2013
H
I
D
DD
H
H
R1CO2CH2
9701/11/M/J/13
[Turn over
HH HH RR
1CO
2CH
1CO
2CH
2 2
CH3(CH2)6C
C(CH2)7CO2CH
CH3(CH
C(CH
CH
C(CH
3(CH
6C
7CO
2CH
2)26)C
2)27)CO
2CH
9701/11/O/N/12
H
R1CO2CH2
H
R11CO
CO22CH
CH22
H
R
C(CH2)7CO2CH
C(CH22))77CO
CO22CH
CH
C(CH
R1CO2CH2
R
R11CO
CO22CH
CH22
9701/11/M/J/13
R2CO2CH2
RR
2CO
2CH
2 2
2CO
2CH
[Turn over
222
The intermediate, Q, is hydrolysed with boiling aqueous sodium hydroxide, to give sodium
propanoate.
29 How many isomeric esters, including structural isomers and stereoisomers, can be made with the
Which reagent
would
the intermediate, Q, from chloroethane?
molecular
formula
C5Hproduce
csonn_topical_MCQs
10O2, if methanoic acid is one of the two reactants used?
A
A
2concentrated ammonia
B 3 solution
C
4
D
5
B June13.13/30
dilute sulfuric acid
45)
FCCl F2 can
be converted into CH2FCF3 by the following route.
30 CCl
C 2hydrogen
cyanide
8
potassium cyanide
step 1
step 2
step 3
CCl 2FCCl F2
CCl 3CF3
CCl 2FCF3
CH2FCF3
20 Ethene reacts with steam in the presence of sulfuric acid.
8
24 Aqueous sodium hydroxide reacts with 1-bromopropane to give propan-1-ol.
What type of reaction is step 1? C2H4 + H2O → CH3CH2OH
18 Transition metals and their compounds
are used as catalysts.
How should the first step in the mechanism be described?
A
addition
What
type of reaction is this?
Which row is correct?
A
by
a curly arrow from a lone pair on the OH– ion to the Cδ+ atom of 1-bromopropane
B
A elimination
acid / base
D
B isomerisation
by atransition
curly arrow
from
the Cδ+ atom
of 1-bromopropane
metal
present
transition
metal present to the OH– ion
C
B addition
in the catalyst used in
in the catalyst used in
C oxidation
by a curly
arrow from
the C–Br bond
the Cprocess
atom
the
Contact
process
the to
Haber
D
C hydrolysis
D by the homolytic fission of the C–Br bond
iron
D A substitution iron
46)BJune13.11/25
iron
vanadium
25 Pentane, C5H12, is reacted with chlorine in the presence of ultraviolet light. A compound R is
21 found
What
of vanadium
every nucleophile?
C is
ironC5H10Cl 2. Each molecule of R contains one chiral
in true
the products.
R has molecular formula
carbon
atom.
vanadium
A D It attacks avanadium
double bond.
Which
two aatoms
of the
B It has
lone pair
of pentane
electrons.chain could be bonded to chlorine atoms in this isomer?
19 Consecutive elements
and5Z are in the
third
period
of theDPeriodic
Element Y has the
B X,1Yand
C
2 and
3
2 and Table.
4
atom.
9701/13/M/J/13
highest first ionisation energy and the lowest
melting point of these three elements.
D It is negatively charged.
What could be the identities of X, Y and Z?
A
1
3
C 2013
It and
is a single
© UCLES
47) June13.13/22
A sodium,
magnesium,
aluminium
22 How
many isomers,
including
structural and stereoisomers, with the formula C4H8 have structures
that involve π bonding?
B magnesium, aluminium, silicon
A
C
1aluminium, silicon,
B phosphorus
2
D
silicon, phosphorus, sulfur
has a characteristic smell caused
partly by the following compound.
9701/11/M/J/13
Nov13.11/20
48)
C
3
D
4
23UCLES
Burnt
sugar
©
2013
20 A new industrial preparation of ethyl ethanoate
has been developed using cheap sources of
O
ethanol.
CH3
C
CHO
Cu catalyst
Cu catalyst
CH3CH2OH
CH3CHO
CH3CH(OH)OCH2CH3
This compound contains
two functional groups. + CH3CH2OH
–2[H]
Cu catalyst
Which reagent will react with both functional groups?
–2[H]
A
acidified potassium dichromate(VI)
B
Fehling’s solution
CH3CO2CH2CH3
Which
processcyanide
is involved at some stage in this reaction sequence?
C
hydrogen
D
A
sodium
hydroxide
electrophilic
addition
B
nucleophilic addition
C
nucleophilic substitution
D
reduction
© UCLES 2013
9701/13/M/J/13
© UCLES 2013
9701/11/O/N/13
223
A
CH3CH2CH(OH)CH(OH)CH2CO2H
B
CH3CH2COCOCH2CO2H
csonn_topical_MCQs
C CH3CH2CH=CHCH2CO2H
D
CH3CH2CO2H and HO2CCH2CO2H
49) Nov13.11/23
23 Which compound exhibits stereoisomerism?
A
CH3CHCl CH3
B
CH3CHCl CH2Cl
C
CH3CCl 2CH3
D
CH2Cl CH2CH2Cl
24 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.
The reaction between aqueous sodium hydroxide and 1-bromobutane proceeds by an SN2
mechanism.
How should the first step in the mechanism be described?
A
attack by a nucleophile on a carbon atom with a partial positive charge
B
heterolytic bond fission followed by an attack by an electrophile on a carbanion
C
heterolytic bond fission followed by an attack by a nucleophile on a carbocation
D
homolytic bond fission followed by an attack by a nucleophile on a carbocation
© UCLES 2013
9701/11/O/N/13
[Turn over
224
What property makes sulphur dioxide useful in this role?
A It is a gas.
csonn_topical_MCQs
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.
Hydrocarbons
1) June02/19
19 The anaesthetic halothane, CF3CHBrCl , is made industrially as shown below.
HF
Br2
CCl2=CHCl ⎯⎯→ CF3CH2Cl ⎯⎯→ CF3CHBrCl
stage 1 811
stage 2
Section B
type of reaction
occurring in stage 2?
23 What
2-Bromopropane,
(CH3)is
2CHBr, may be used as the starting point for making (CH3)2CHCO2H.
For each of the questions in this section, one or more of the three numbered statements 1 to 3 may be
Which
of the following
sequences would be most suitable?
A
electrophilic
addition
correct.
B
electrophilic
substitution
A (CH
→
(CH )2CHOH → (CH3)2CHCO2H
3)2CHBr
Decide whether
each of the 3statements
is or is not correct (you may find it helpful to put a tick against
C
free3)radical
substitution
the statements
that
you
consider
to
be
correct).
CHBr
→
(CH
)
CHCN
→
(CH
B (CH
2
3 2
3)2CHCO2H
(CH3)2be
CHOH
→ (CH
C
(CH
nucleophilic
addition
3)2CHBr
2CHCN
The D
responses
A to D→
should
selected
on3)the
basis→of(CH3)2CHCO2H
D (CH3)2CHBr → (CH3)2CHCN → (CH3)2CHOH → (CH3)2CHCO2H
2) June02/24
A
B
C
D
24 Which substance
in a3vehicle
from
hydrocarbon fuel?
1, 2 and
are exhaust
1 and 2 results
only are
and 3 onlycombustion
are 1 onlyofisa correct
7 2incomplete
correct
correct
correct
C of N
D9701/1/M/J/02
NO and HI are –92 kJ mol–1 and +26 kJ mol–1
B H2Ochanges
17 A
The CO
standard enthalpy
formation
of HCl
2
respectively.
No other combination of statements is used as a correct response.
25 Which
compoundisonmost
reaction
with hydrogen
cyanide
produces a compound with a chiral centre?
statement
important
in explaining
3)Which
June02/31
13 this difference?
31 A
Which
pairs
of compounds
have the same
empirical formula?
CH
A
Chlorine
moreform
electronegative
3CHOissalts
37 Which
sodium
a precipitatethan
wheniodine.
AgNO3(aq) followed by dilute NH3(aq) is added to its
aqueous
solution?
COCH
B
B
The
activation
energy
3CH
2and
2CH3 for the H /Cl reaction is much less than that for the H /I reaction.
1 CH
ethane
ethene
2
C
1C
2
D
2D
3
26
18
32
38
2
2 2
CH
CH
The
bond
energy
of HI is smaller than the bond energy of HCl.
chloride
3CO
2and
3cyclohexane
ethene
HCHO
The
bond energy
I2 is smaller than the bond energy of Cl2.
bromide
cyclohexane
andofoct-1-ene
3
iodide
) on
An
organic
compound
will decolorise
acidified aqueous
potassium
manganate(
the
industrial
electrolysis
of brine
to dilute
manufacture
diaphragm
usedangle
is a VII
porous
4)In
InJune02/38
which
sequences
are the
molecules
quoted inchlorine,
order ofthe
increasing
bond
within the
warming,
but will
not the
decolorise
bromine water.
screen which
allows
flow of electrolytes
but keeps other chemicals separate.
molecule?
Which
compounds would be formed in the reaction of ethene with aqueous bromine in the
presence
of the
sodium
chloride?
What
organic
compound
Whichcould
substance
needs
to be kept be?
separate from the chlorine by the diaphragm?
1
H2O
NH3
CH4
1A
CH
ClCH2Cl
A
hydrogen
2 butane
H22O
SF6
BF3
BrCH
Cl
2B
CH
2 CO
B
sodium
3 ethanol
CH24 hydroxide
SF6
2
BrCH
Br
3C
CH
ethene
2
2
C sodium
chloride
D
water
33 D
The ethanoic
conceptsacid
of bond energy, bond length and bond polarity are useful when comparing the
39 Halogenoalkanes
react
with aqueous
alkali. stability.
One mechanism of this reaction has the reaction
behaviour
of similar
molecules,
e.g. thermal
5)
Nov02/19
pathway diagram shown below.
27
compound
all in
of the
properties:
19 A
Which
gas is Xpresent
exhaust fumes
of a car engine in a much greater amount than any
For
example,
ithas
could
be
saidfollowing
other gas?
Z
it iswith
a liquid
room
temperature
and ……….X………….
atmospheric
pressure;
“Compared
the at
HCl
molecule,
the bond
of the HI molecule is
A
carbon
dioxide
………..Y………..
.”
it does not mix completely with water;
B carbon monoxide
Y
it does
not decolorise
potassium
manganate(
Which pairs
of words
correctlyacidified
complete
the above
sentence?VII).
C nitrogen energy
What could X be?
D water
X
X vapour Y
A ethane
R – Hal + OH–
1
energy greater
20 B
The Russian
Borodin was also a research chemist who discovered
a reaction in which
ethanoic composer
acid
–
ROH
+ Hal
2 ethanal
lengthmolecules
greatercombine to form a compound commonly
two
known
as aldol (reaction I). Aldol
C
formsethanol
another compound on heating (reaction II).
3
polarity
less
225
reaction pathway
D ethyl ethanoate
I 2CH3CHO → CH3CH(OH)CH2CHO
Which of the
following
statements are correct?
II CH
+ H2O
9701/1/M/J/02
3CH(OH)CH2CHO → CH3CH=CHCHO
plastics,
but are react
now known
destroy
36 foamed
Ammonia
and chlorine
in the to
gas
phase.ozone in the upper atmosphere.
Which of the
following
will not destroy ozone, and therefore can be used safely as a replacement
8NH
3 + 3Cl2 → N2 + 6NH4Cl
for
CFCs?
csonn_topical_MCQs
Which statements are correct?
B CCl3CBr3
A CHBr3
7
C
CHClFCClF2
D
CH3CH2CH2CH3
21 6)
The
isomers,
citric
acid and
acid, agent.
are intermediates in the Krebs cycle of the oxidation of
1 Nov02/26
Ammonia
behaves
asisocitric
a reducing
glucose in living cells.
26 Oxidation
of an alkene
Y as
gives
a diol; further oxidation gives a diketone.
2
Ammonia
behaves
a base.
CH2CO
CH2CO2H
3
The
oxidation
of2Hthe hydrogen changes.
What
could
be Y? number
C(OH)CO H
2
A CH3CH=C(CH3)2
37 Which compounds show cis-trans isomerism?
B (CH3)2CHCH=CH2CH2CO2H
C1 Cbut-2-ene
H CH=CHC H
6 5
6 5
citric acid
CHCO2H
CH(OH)CO2H
isocitric acid
but-1-ene
=
D2 (C
6H5)2C CHCH3
How many chiral centres does each acid possess?
3
2-methylpropene
Nov02/38
27 7)
Burnt
sugar has a characteristic smell caused partly by the following compound. It has two
citric acid
isocitric acid
functional
groups
indicated by
Q and R.cracking, which compounds can be obtained?
38 When octane
is subjected
to catalytic
A
0
1
1
B
CH2=CH2
C2
CH31CH2CH=CH21
0
2
Q
O
CH3
C
R
CHO
CH31(CH2)4CH3 2
D3
When this compound is tested in a laboratory with 2,4-dinitrophenylhydrazine and Fehling’s reagent,
8)
June03/22;
June13.12/20;
Nov13.11/22
(used dichromate/H+)
which
functional Nov08/21;
groups are responsible
for positive
tests?
39 The
Which
ions arehex-3-en-1-ol,
present in a solution
ethanol
in ansmell
excess
of concentrated
sulphuric
22
compound
P, has aofstrong
‘leafy’
of newly
cut grass and
is usedacid?
in
perfumery.
2,4-dinitrophenylhydazine
1
Fehling’s reagent
CH3CH2O–
A2
+
CH3CH2CH=CHCH
Q and R 2CH2OH
CH3CH2OH2
Q and R
B3
HSO–4
RPonly
Q and R
What is produced
when
C
Q and
R P is treated with anRexcess
only of hot concentrated acidic KMnO4?
Qbetween
only
R only
40 D
an aldehyde and
HCN catalysed by NaCN, which statements about the
AIn the
CHreaction
3CH2CH(OH)CH(OH)CH2CH2OH
reaction mechanism are true?
B CH3CH2CH=CHCH2CO2H
[Turn over
9701/1/O/N/02
1
A
new
carbon-carbon
bond
is
formed.
C CH3CH2CHO and OCHCH2CH2OH
D2
3
CH
CH2intermediate,
CO2H and HOthe
In 3the
oxygen
2CCH
2CO2Hcarried a negative charge.
The last stage involves the formation of a hydrogen-oxygen bond.
8
9) June03/23
23 The complete combustion of alkanes to produce
carbon dioxide and water is an important
9701/1/O/N/02
exothermic reaction.
Which line on the graph shows the relationship between the number of carbon atoms in the alkane
and the number of moles of oxygen gas needed for complete combustion of the alkane?
A
B
C
number of
moles of
oxygen gas
[Turn over
9701/1/M/J/03
D
1
number of carbon atoms in alkane
24 Cyclohexa-1,4–diene is treated with a solution of bromine in tetrachloromethane.
226
oxygen gas
DD
D
11
1 number
numberof
ofcarbon
carbonatoms
atomsininalkane
alkane
number of carbon atoms in alkane
csonn_topical_MCQs
10) June03/24
Cyclohexa-1,4–diene is
with
solution
of
bromine
inintetrachloromethane.
24
is treated
treated with
withaaasolution
solutionof
ofbromine
brominein
tetrachloromethane.
24 Cyclohexa-1,4–diene
Cyclohexa-1,4–diene is
treated
tetrachloromethane.
cyclohexa-1,4-diene
cyclohexa-1,4-diene
cyclohexa-1,4-diene
Which
Which product
product is
formed?
Which
product
is formed?
formed?
A
A
BBB
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
DD
D
C
C
C
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
Br
9701/1/M/J/03
9701/1/M/J/03
9701/1/M/J/03
9
11) June03/25
25 Which reaction is not an electrophilic addition?
A
CH2=CH2 + HI ⎯→ CH3CH2I
B
CH3CH=CH2 + Br2 ⎯→ CH3CHBrCH2Br
C
2
4
CH3CH=CH2 + H2O ⎯⎯⎯→
CH3CH(OH)CH3
D
CH3CHO + HCN ⎯→ CH3CH(OH)CN
conc H SO
26 The reaction scheme outlines the production of one of the monomers of nylon 66 from
compound X.
KCN
reduction
H2N(CH2)6NH2
compound X
NCCH2CH2CH2CH2CN
in ethanol
Which compound could be X?
A
BrCH2CH2CH2CH2Br
B
CH2=CHCH=CH2
C
HOCH2CH2CH2CH2OH
D
HO2CCH2CH2CH2CH2CO2H
227
H3C
C
C
C
H
csonn_topical_MCQs
C
C
OH
H
sorbic acid
10
Sorbic
acid will react with
12)
June03/29
29 In a preparation of ethene, ethanol is added a drop at a time to a heated reagent Y. To purify the
• hydrogen in the presence of a nickel catalyst,
ethene it is bubbled through a solution Z and then collected.
• bromine in an organic solvent.
What could reagent Y and solution Z be?
How many moles of hydrogen and of bromine will be incorporated into one mole of sorbic acid by
these reactions?
reagent Y
solution Z
A
moles of Khydrogen
acidified
2Cr2O7
moles
of bromine
dilute
NaOH
BA
concentrated
2 H2SO4
dilute2 H2SO4
CB
concentrated
2 H2SO4
dilute
2 21 NaOH
DC
ethanolic3 NaOH
concentrated
H2SO4
2
1
D
3
22
Nov09.11/25;
June13.11/22
3013)
TheNov03/21;
product of the
reaction between
propanone and hydrogen cyanide is hydrolysed under acidic
8
conditions.
25 Bromine reacts with ethene to form 1,2-dibromoethane.
21 Hydrogen
bromide
to form bromoethane.
What is the
formulareacts
of thewith
finalethene
product?
What is the correct description of the organic intermediate in this reaction?
What is the
best description
of the organic intermediate in this reaction?
H
AA It CH
has3CH(OH)CO
a negative 2charge.
AB ItItCH
contains
carbon,
2CH
2CO2Hhydrogen and bromine.
B
is
a3CH
free
radical.
BC
C
CD
D
D
(CH
)a2CHCONH
has
negative charge.
2
ItIt is
a3nucleophile.
(CH
C(OH)CO2H
is an
an
3)2electrophile.
ItIt is
electrophile.
It is a free radical.
Nov03/22
26 14)
Which
equation represents a valid propagation13
step in the free radical reaction between ethane
chlorine?
22 and
On strong
heating a hydrocarbon produces ethene, propane and but-1-ene in the mole ratio
36 Which
5 : 1 : 1.processes involve the conversion of sulphur dioxide into sulphur trioxide?
A C2H6 + Cl • → C2H5Cl + H•
What
is the
molecular
formula
hydrocarbon?
•
• of the
1
combustion
of
sulphur
contaminated
carbonaceous fuels
B
Cthe
2H5Cl + Cl → C2H4Cl + HCl
2
theHContact
process
for manufacturing
•
B H• C
H
C C19Hsulphuric
DacidC19H40
A CC
34H → C
36
38
H6 +
HCl
C
2 5 + 17
217
3
the catalytic oxidation of sulphur dioxide by oxides of nitrogen
D C2H5• + Cl • → C2H5Cl
23 15)
1,2-Dibromo-3-chloropropane
(DBCP) has been used in the control of earthworms in agricultural
Nov03/37
land.
37 Which molecules would be present in the photochemical chlorination of methane?
What would be the best synthesis of this compound?
1
hydrogen
A CH3CH2CH2Cl + 2Br2 → DBCP + 2HBr
2
hydrogen chloride
© UCLES 2009
9701/11/O/N/09
[Turn over
B CH3CHBrCH2Br + Cl2 → DBCP + HCl
3
dichloromethane
C CH2=CHCH2Cl + Br2 → DBCP
8
D ClCH2CH=CH2 + PBr5 → DBCP + PBr3
38 16)
TheJune04/23
taste buds on the tongue are chiral and can distinguish one optical isomer from another.
23 Which compound could not be obtained from cracking a sample of nonane, CH3(CH2)7CH3?
compounds
willashave
optical isomers that may be distinguished by
24 Which
Each of naturally-occurring
the following compounds
is effective
a refrigerant.
taste?
A
CH3CH=CHCH=CHCH2CH2CH2CH3
The release of which one of these causes the greatest depletion of the ozone layer?
B
A
C
HD
CH3CH2CH2CH2CH3
O
CH
F
B CH3OCH3
CCl2CH
CH
3 2 2CH2CH2CH2CH=CH
2
C CH
OH CH ) CH
(CH
3
2
CH3
C
CH3CHF2
9701/1/M/J/03
D
CH3CH2CH3
O
O
2 3
25 1,1-Dichloropropane reacts with aqueous sodium hydroxide in a series of steps to give propanal.
HO
3
OH
NaOH(aq)
24 In which way are ethene and propaneCH
similar?
H
C OH
CH3CH2CHCl2 ⎯⎯⎯⎯→ CH3CH2CHO
CH3
CH3
CH3CH2CH3
CH2=CH2
CH
OH
What
is
the
mechanism
of
the
first
step
of
this
reaction?
2
ethene
propane
1
H
C
OH
2
A ribose
electrophilic substitution
A
B
menthol
They
are both obtained by the dehydration of alcohols.
elimination
C
CH
CH
C
228
maleic acid
OH
A
B
CH3CH=CHCH=CHCH2CH2CH2CH3
CH3
CH3CH2CH2CH2CH3
CH3
C CH3CH2CH2CH2CH2CH=CH2
csonn_topical_MCQs
CH3
D (CH3CH2CH2)3CH
CH3
17) June04/24
C+ +
CH3
OH
_
fast
C
CH3
24 In which way are ethene and propane similar?
CH3
OH
CH3
CH3CH2CH3
CH2=CH2
Which diagram represents the
reaction profile for this mechanism?
ethene
propane
D
C
They can both be hydrogenated using a suitable catalyst.
D
They can both undergo polymerisation under suitable conditions.
reaction path
reaction path
energy
They are both neutral to an indicator solution.
energy
B
energy
A
B
C
They are both obtained by the dehydration of alcohols.
energy
A
reaction path
reaction path
June04/27
25 18)
Which
reaction in the catalytic converter does not remove hazardous and polluting gases from
exhaust
fumes
of a motor
car? to give two products, CH2BrCH2Br and CH2BrCH2OH.
27 the
Ethene
reacts
with aqueous
bromine
Which statement is correct for these products?
gases going out
A
Both products are obtained in this reaction by electrophilic substitution.
B
Both products are obtained in this reaction by nucleophilic addition.
C
Both products can be hydrolysed to form the same diol.
gases going in:
D Both
products can form hydrogen bonds with water.
carbon
monoxide,
hydrocarbons
and oxides ofJune08/27
19) June04/28;
nitrogen
28 Compound X
surfaces coated
with platinum and
rhodium catalyst
10
These equations are !qualitative
unbalanced.
has the and
molecular
formula C10H14O;
[HC = unburnt hydrocarbons;
NO
=
oxides
of mild
nitrogen]
x
! is unreactive towards
oxidising agents.
A HC
+ NO
COcompound
+ N2
x ! H 2O
What
is the
structure
of +the
formed by dehydration of X?
B
C
D
CO + NOx ! CO2 + N2
A
HC + NOx ! H2O + CO2 + N2
CH2 CH2 CH CH2
CO + O2 ! CO2
! UCLES 2004
C
B
CH2
CH
D
9701/01/M/J/04
CH3
CH
CH
CH3
[Turn over
CH3
CH
CH2
! UCLES 2004
C
CH
CH3
9701/01/M/J/04
29 For which pair of compounds can the members be distinguished by means of Tollens’ test (the
use of a solution containing Ag(NH3) 2! )?
A
CH3CHO and CH3COCH3
B
CH3COCH3 and C2H5COCH3
C
CH3COCH3 and CH3CO2CH3
D
CH3CO2H and CH3CO2CH3
229
30 Compound X changes the colour of acidified sodium dichromate(VI) from orange to green. 1 mol
of X reacts with 2 mol of HCN(g).
A
X will undergo nucleophilic addition.
B
Y will undergo nucleophilic addition.
C X will undergo electrophilic substitution.
csonn_topical_MCQs
D
Y will undergo electrophilic substitution.
20) Nov04/25
25 Which reaction occurs with saturated hydrocarbons?
A
catalytic hydrogenation
B
ready decolourisation of aqueous bromine
C
polymerisation
D
thermal cracking
9
26 21)
TheJune05/22
reaction of chlorine with methane is carried
out in the presence of light.
9
22 When bromine reacts with propene in an organic solvent at room temperature, what is the
which
the
bromine
attacks
22 mechanism
When
reacts
propene
in the
an propene?
organic solvent at room temperature, what is the
What isbromine
thebyfunction
ofwith
the light?
mechanism by which the bromine attacks the propene?
A
A electrophilic
to break theaddition
C – H bonds in methane
A electrophilic addition
B electrophilic substitution
B to break up the chlorine molecules into atoms
B electrophilic substitution
C nucleophilic addition
C
C
D
D
to break up the chlorine molecules into ions
8
to heat up the mixture
nucleophilicsubstitution
addition
nucleophilic
D nucleophilic substitution
19 Bromomethane, CH3Br, is used as a fumigant to destroy insect pests in grain that is to be stored.
23 22)
Dichlorodifluoromethane,
CClmethanol
in aerosol
propellants and as a refrigerant.
June05/23
2F2, has been
It can
be made by reacting
withused
hydrogen
bromide.
23 Dichlorodifluoromethane, CCl2F2, has been used in aerosol propellants and as a refrigerant.
Which statement helps to explain
dichlorodifluoromethane is chemically inert?
CHwhy
3OH + HBr → CH3Br + H2O
Which
helps to
explain
why
is chemically inert?
A
Thestatement
carbon-fluorine
bond
energy
is dichlorodifluoromethane
large.
What type of reaction is this?
A The
The carbon-fluorine
carbon-fluorinebond
bondhas
energy
large.
B
a lowispolarity.
A condensation
B Fluorine
The carbon-fluorine
bond has a low polarity.
C
is highly electronegative.
B electrophilic substitution
D
are non-flammable.
C Fluorine
Fluorine compounds
is highly electronegative.
C Fluorine
free radical
substitution
D
compounds
are non-flammable.
D nucleophilic
substitution
24 Under
identical conditions,
even though it proceeds
by the same mechanism, reaction 1 is faster
9701/01/O/N/04
[Turn over
than reaction 2.
June05/20
24 23)
Under
identical conditions, even though it proceeds by the same mechanism, reaction 1 is faster
reaction
reaction
1 2. (allyl
CH3CHBrCH
+ NaCN
→ CH3CH(CN)CH
20 than
Prop-2-en-1-ol
alcohol) 3has
the following
structure.3 + NaBr
© UCLES 2004
reaction
reaction 21
CH
3 + NaI → CH3CHICH3 + NaBr
CH3CHBrCH
3CHBrCH3 + NaCN → CH3CH(CN)CH3 + NaBr
H
H
H
reaction
CH3CHBrCH
3 + NaI → CH3CHICH3 + NaBr
What
factor 2
will explain
this result?
C
C
A
C will
I bond
is athis
stronger
bond than the C
WhatThe
factor
explain
result?
H
C
OH
Br bond.
H bond.
B
NI bond
bond is
is a
A The
The C
C
a stronger
stronger bond
bondthan
thanthe
theCC I Br
bond.
C
Thereagent
cyanidewould
ion is a stronger
than the iodideproduct
ion.
Which
with nucleophile
prop-2-en-1-ol
that could exist as optical
B
The C
N bond react
is a stronger
bond than thetoCformI abond.
isomers?
D The cyanide ion is a weaker nucleophile than the iodide ion.
C The cyanide ion is a stronger nucleophile than the iodide ion.
A
D
B
bromine
The cyanide ion is a weaker nucleophile than the iodide ion.
hydrogen and nickel
C
phosphorus pentachloride
D
sodium
21 Under the Montreal Protocol the use of chlorofluorocarbons is to be phased out. Fluorocarbons
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.
step 1
CCl2FCCl F2
What type of reaction is step 1?
step 2
CCl3CF3
step 3
CCl2FCF3
CH2FCF3
230