Organic Workbook
Organic Workbook
Organic Workbook
OL Chemistry
Organic Workbook 2021
Abul Fazal
alt
Contents
Intro to Organic WS 5
alt
Alkanes WS 9
Alkenes WS 20
Alcohols WS 29
Carboxylic Acids WS 37
Organic Chemistry WS 43
alt
3
Homework
alt
Date Particulars
4
Homework
alt
Date Particulars
In which steps is a catalyst used?
A step Q only
5
B step R only
C steps Q and R only Intro to Organic WS
D steps P and Q and R
alt
11
1 2014 SUM P12 Q32
33 Two esters have the same molecular formula,12 C3H6O2.
32 Which property of compounds in a homologous series is correct?
What are the names 12
33 Which
A Theycompound, onofcombustion,
all have the
these two esters?
same generalnever forms carbon?
formula.
33 Which compound, on combustion, never forms carbon?
A They1allmonoxide
B carbon methyl
have theethanoate
same molecular formula.
A
C carbon
B They2allmonoxide
ethanol ethyl the
have propanoate
same number of isomers.
B
C
D ethanol
They3all have
ethene ethyl the
methanoate
same physical properties.
C
D ethene
4 propyl methanoate
methane
2 2014
D 1 SUM
and 2P12 Q34
A methane B 1 and 3 C 2 and 4 D 3 and 4
© UCLES 2014 5070/12/M/J/14
34 Which process is an example of cracking? [Turn over
34
34 Which
Which process is is
statement ancorrect?
example of cracking?
A C2H 4 + H2O → C2H5OH
A
B C32H
C H64 +
+ H
H22O→→C3CH28H5OH O
A
B
C
Carboxylic
C
C3H6 + H2 acids
→ Ccontain
3H8 the functional group C .
3H8 + 5O2 → 3CO2 + 4H2O
H
C
D C3H
C 8 + 5O2 → 3CO2 + 4H2O
4H10 → C2H4 + C2H6
B Ethanoic acid will react and fizz when copper is added.
D C4H10 → C2H4 + C2H6
3 2014
35 A SUM
C hydride is P12
Ethanol awill Q35 containing
decolourise
compound acidifiedonly
potassium manganate(
two elements, one VII ).
of which is hydrogen.
O elements,
35 A hydride is a compound containing only two H one of which is hydrogen.
Which element can form the greatest number of different hydrides?
D The
Which structure
element
A carbon canofform
ethylthe
ethanoate H C of different
greatestisnumber O C hydrides?
H.
A
B carbon
chlorine H
B
C chlorine
nitrogen
35 C
When cracked, one mole of a compound, X, produces one mole of propene and one mole of
D nitrogen
oxygen
hydrogen.
D oxygen
X → C H6 + H2
36 A liquid reacts with each of sodium carbonate,3 potassium hydroxide and ethanol.
5
4 2014
36 A
What
What isWIN
liquid
theP11
reacts
type Q10each isofX?
with
of compound
liquid?
sodium carbonate, potassium hydroxide and ethanol.
10 A
A volume of ethane, C2H6, at r.t.p. has a mass of 20 g.
anis alcohol
What
A aqueous the liquid?
ammonia
Whataqueous
B
A anisalkane
the mass of an equal volume of propene, C3H6, at r.t.p.?
ammonia
B ethanoic acid
C
A an
B 20 galkeneacid B 21 g C 28 g D 42 g
C ethanoic
ethyl ethanoate
D a carboxylic
C acid
D ethyl
sodium ethanoate
hydroxide
5 2015
11 WhichSUM elementP11requires
Q36 the largest number of electrons for one mole of the metal to be formed
D
fromsodium hydroxide
its aqueous ions during electrolysis?
36 Which is a correct definition of isomers?
A aluminium
A atoms with the same relative atomic mass and different structures
B calcium
B compounds with the same molecular formula and different structures
C copper
C compounds with the same molecular mass and different structures
D sodium
D elements with the same molecular mass and the same structures
12 Which changes are observed during the electrolysis of aqueous copper(II) sulfate using copper
electrodes?
Abul Fazal Intro to Organic WS
© UCLES 2015 5070/11/M/J/15 [Turn over
1 A pink solid is deposited on the negative electrode.
2 Bubbles form on the positive electrode.
C CO is poisonous to humans
D NO2 forms acid rain
12
6
32
35 Pollutant gases areisreleased
Which compound the mostby the bacterial
viscous and thedecay of vegetable matter.
least flammable?
6 2016 SUM P12 Q34
The C6H14 decay of
A bacterial B vegetable
C8H18 matter isC theCmain
10H22 source ofD C12gas?
which H26
alt
34 34
How many of the structures show an unsaturated hydrocarbon molecule?
How many of the structures show an unsaturated hydrocarbon molecule?
A carbon monoxide
36 How many moles of ethanoic acid, CH3CO2H, react with one mole of magnesium? HH
B methane
A 1 B 2 C 3 D 4 HH CC HH
C nitrogen dioxide
H HH H H HH H H H HH HH
D sulfur dioxide HH OO
37
C CWith
C Cwhich substance
H H C C will
C Cethene
C C react to form
H Hmore
C Cthan
C Cone product? HH CC CC CC HH
A H argon HH OO HH
Cl Cl
33 Lakes
H H H of dissolved substances. H H
contain a variety HH HH HH
B hydrogen
Which substance is responsible for eutrophication in lakes?
C A1oxygen
A 1 B B2 2 CC 3 3 DD 4 4
A metal compounds
D steam
B nitrate fertilisers
7 2016
35 35
Which WIN
Which P12 Q38
statements
statements areare correct
correct forfor alkenes
alkenes butbut not
not forfor alkanes?
alkanes?
38 C oxygen
Which statement about isomers of bromine
a compound is always correct?
1 1 TheyThey turn
turn aqueous
aqueous bromine from from brown
brown totocolourless.
colourless.
D sulfuric acid
A They2 have different
2 Their
Their empirical
general
general formulae.
formula
formula HnH.2n.
is C
is C n 2n
O 2016
C
© UCLES 2016
© UCLES O CH3 CH2 CH2 H
CH3 H CH3
5070/12/M/J/16
5070/12/M/J/16 CH CH2 CH3 C
H
C O H
H C C C H
A 1 B 2 C 3 D 4
H H H
A It is a saturated hydrocarbon.
© UCLES 2016 5070/12/O/N/16 [Turn over
B It is an alkene.
C It is an isomer of butane.
D It will undergo addition with hydrogen.
12
9 2019 WIN P11 Q32
32 Which statements are true for homologous series?
alt
1 Each series contains saturated compounds.
2 The compounds in each series are unreactive.
3 Each series has a general formula.
4 Each series has a gradation in physical properties.
A 1, 2, 3 and 4
B 1, 2, and 3 only
C 1 and 4 only
D 3 and 4 only
1 2
H
H C H H H H H H
H H H H C C C C C H
H C C C C H H H H H
H H H H C H
H C H H
H
3 4
H
H H
H H H C H
C C H H H H
H H
C C H C C C C C H
H H
C C H H H H
H H
H H H C H
Answers
1
alt
A
2 D
3 A
4 C
5 B
6 A
7 D
8 A
9 D
alt
13
1 2018 WIN P11 Q36
D methane
36 Which statement about vegetable oil and the margarine made from it is correct?
A Both
35 Which are following
of the liquids atisroom
not temperature.
a condensation polymer?
B
A Both occur naturally.
nylon
C
B Margarine has the higher melting point.
poly(ethene)
D
C Vegetable oil has fewer carbon-carbon double bonds than margarine.
protein
D Terylene
37 WhichSUM
2 2014 group P11
is found
Q36in alcohols?
2H C CONH
A C=C
36 Which B the
statement about COproperties of propane and hexaneDis correct?
OH
A Propane has a higher boiling point than hexane.
38 B
An ester is formed
Propane has afrom a carboxylic
higher acid andmass
relative molecular an alcohol.
than hexane.
HowPropane
C does thehas
number of carbon,
more isomers thanhydrogen
hexane. and oxygen atoms in an ester differ from the total
number of these atoms in the carboxylic acid and alcohol from which the ester is formed?
D Propane is more flammable than hexane.
carbon atoms hydrogen atoms oxygen atoms
12
3 2014
37 A WIN
When P11 Q36
fewer
a volcano fewer
erupts, which gas is produced fewer
in significant amounts?
A B carbon
36 Methane
fewer
is the
same fewer
first member of the alkane series of hydrocarbons. The second member is ethane.
monoxide
B C methane
Which same about ethane
statements fewer
are correct? fewer
C D ozone
1 same
Ethane has the same
formula C2H4. same
D sulfur
2 dioxide
Ethane has a higher boiling point than that of methane.
39 Which statement
3 Ethane about
hasthe
thecomposition of polymers
same molecular formulaisascorrect?
methane.
A Nylon 4 contains
Ethaneoxygen atoms properties
but not nitrogen atoms.to those of methane.
38 Four compounds are shown.
has chemical very similar
H
B O
Proteins contain both nitrogenHatoms
O and
H oxygen atoms.
O D H O H
A 1, 2 and 3 B 1 and 4 C 2 and 4 3 only
H C
C C
Terylene H
Hcontains nitrogen C C H
H atoms.
C C C H C C H
DH The Opolymer
C when
C
usedHto make clingfilm atom
contains oxygen atoms.
H by a H O not H
H will
H H
37 Which alkane, any one hydrogen is substituted chlorine atom, produce
isomers?
H H
2 3 4
1 A B
H have
Which pair of compounds H the same empirical formula? H H H
H C C H H C C C H
A 1 and 2 B 1 and 3 C 2 and 3 D 2 and 4
H H H H H
H H H H H H H
H C C C C H H C C C H
H H H H H H
H C H
© UCLES 2018 5070/11/O/N/18 [Turn over
Abul Fazal H Alkanes WS
2 Ethane has a higher boiling point than that of methane.
3 Ethane has the same molecular formula as methane.
4 10very similar to those of methane.
Ethane has chemical properties
alt
isomers?
A B
12
H H H H H
38 When butene reacts with bromine, which compound could be made?
H C C H H C C C H
A B
H H H H H
Br H H H 11 Br Br H H
H C
33 Two esters have the same C H
C molecular
C formula, C3H6O2. H C C C C H
C D
Br ofHthese
What are the names H twoHesters? H H H H
H H H H H H H
1 methyl ethanoate
H C C C C H H C C C H
C
2 ethyl propanoate D
3 ethylH H H
Brmethanoate
Br H
H
Br
H H
H HH CH H Br
4 propyl methanoate
H C C C C H H C C HC C H
A 1 and 2 B 1 and 3 C 2 and 4 D 3 and 4
H H H H H H H H
5 2014
38 When WIN P12
ethanol Q39with ethanoic acid, the ester ethyl ethanoate is formed.
reacts
34 Which statement is correct?
39 Methane is the first member
C2H5OH of the alkane
+ CH series of hydrocarbons. The second member is ethane.
3CO2H → CH3CO2C2H5 + H2O
O
Which
What statements
is the formula
A Carboxylic about ethane
acidsofcontain
the ester are
theformedcorrect?
when
functional methanol
group C reacts
. with butanoic acid, C3H7CO2H?
B
B Ethanoic
C3H72
acid
CO2Ethane
C 2H5
willhas
react and fizz
a higher whenpoint
boiling copper is added.
than that of methane.
C
C Ethanol
CH 3 2C
3CO
will decolourise
Ethane
3H7 has theacidified potassium
same molecular manganate(
formula VII).
as methane.
D C3H74CO2Ethane
CH3 O very similar
has chemical properties H to those of methane.
D
A The
1, 2 structure
and 3 of B
ethyl1ethanoate
and 4 is H C C 2 and
O 4C H. D 3 only
H
6 2015
40 WhenSUM P11
ethanol Q35with ethanoic acid, the ester ethyl ethanoate is formed.
reacts
A atoms with the same relative atomic mass and different structures
Alkanes WS
B compounds with the same molecular formula and different structures Abul Fazal
C compounds with the same molecular mass and different structures
© UCLES 2014 5070/12/O/N/14
A Alkanes are readily polymerised.
B Alkanes react with bromine by addition.11
CAlkanes react with chlorine by substitution.
12
7 2015 SUMhas
D Butane P12three
Q34more carbon atoms and eight more hydrogen atoms than methane.
34 Which statement about alkanes is correct?
alt
35 Which statement about members of the homologous series of alcohols is correct?
A Alkanes are readily polymerised.
A
B An alcohol
Alkanes withwith
react twobromine
carbon atoms in each molecule is called methanol.
by addition.
B
C Butanol
Alkanes can bewith
react combusted
chlorine to
bygive carbon dioxide and water only.
substitution.
C
D Ethanol is the
Butane has onlymore
three alcohol that atoms
carbon can beand
oxidised
eight to a carboxylic
more hydrogenacid.
atoms than methane.
D Propanol can be made by the catalysed addition of steam to ethene.
8 2015
35 Which SUM P12about
statement Q36 members of the homologous series of alcohols is correct?
36 When cracked, one mole of a compound, X, produces one mole of propene and one mole of
A An alcohol with two carbon atoms in each molecule is called methanol.
hydrogen.
B Butanol can be combusted to give carbon dioxide and water only.
X → C3H6 + H2
C Ethanol is the only alcohol that can be oxidised to a carboxylic acid.
What type of compound is X?
D Propanol can be made by the catalysed addition of steam to ethene.
A an alcohol
36 When
B ancracked,
alkane one mole of a compound, X, produces one mole of propene and one mole of
hydrogen.
C an alkene
D a carboxylic acid X → C3H6 + H2
alt
A B
H
H H
H C H
H C H H C H
H H
H C C H
H C C C H
H H
H H H
C D
H
H
H C H
H H C H H
H C C H H C C H
H C H H H
H C H
H
H
13
11 2015 WIN P12 Q37
37 The structures of three hydrocarbons from the same homologous series are shown.
H C H
H H H H H H
H C H H C C C H H C C C H
H H H H H H H
© UCLES 2015 W X
5070/12/O/N/15 Y [Turn over
A 3 B 4 C 5 D 6
H Cl n
A The monomer is C C. 13
12 2016 SUM P11 Q38
H
Clalkanes
alt
38 Which statement about is correct?
H Cl
A Ethane reacts with chlorine in an addition reaction.
BB Propane
The monomer
has a is
higher C.
C boiling point than butane.
C Cl alkane
The molecule of the H that contains 99 carbon atoms has 200 hydrogen atoms.
DC There
The polymer is formed
are three isomersby a condensation
with the formula Creaction.
4H10.
AC Ithydrogen
These pollutant
undergoes
four terms addition reactions
can be used effect
with chlorine.
to describe polymers.
BD A Itoxygen
has CFCsboiling point
1 a lower
cause depletion of the ozone layer
addition polymer than methane.
C B It has theCO 2
same formsas
general formula photochemical
methane. smog
2 condensation polymer
2 A gas is evolved during a reaction.
D C There areCO four C–C bonds in isthepoisonous
molecule.to humans
3 polyamide
Which
D two piecesNO2 of apparatus wouldformsenable therain
acid rate of this reaction to be measured?
4 polyester
15 A balance
40 2016 WINofP12
Hydrolysis andaQ35
R, pipette
macromolecule, gives a mixture of amino acids.
Which two terms can be applied to polymer Z?
35 What
Which
B gasiscompound
syringe and
R? is the most viscous and the least flammable?
thermometer
AC 1stopclock
and 3 and gas
B syringe
6H14
A aCfat B C8H18 C C10H22 D C12H26
1 and 4 C 2 and 3 D 2 and 4
A
BD astopclock
nylon and pipette
36UCLES
How
2017 many moles of ethanoic acid, CH3CO 2H, react with one mole of magnesium?
16 C a SUM P11 Q03
© 2016 5070/12/M/J/16
polyester
3 A Which
1 statement about 2 hexane, C6HC14, is
B pure 3 correct? D 4
D a protein
A It boils over a range of temperatures.
37 With
B Itwhich
burnssubstance
in excess will ethene
oxygen reactcarbon
to form to formmonoxide
more thanand
onewater
product?
only.
A
C argon
It mixes with water.
B
D hydrogen
It melts at a fixed temperature.
C oxygen
19 20 23 +
4 D steam
Which statement about the particles 9F , 10 Ne and 11Na is correct?
C C C C C C C C
12
17 2017 SUM CH
P113 Q32
Br Cl Br Br Cl H Br
32 Which row correctly compares carbon dioxide and methane?
alt
36 Each of compounds W, X, Y and Z is either an unbranched alkane or anthe
both lower unbranched
pH of alkene.
both contain both are described as
water when they
W C9carbon
H18 a greenhouse gas
dissolve in it
A X C9H20
B Y C10H20
C Z C10H22
3 sulfur dioxide
12
19 2017 SUM P12about
38 Which statement Q34macromolecules is correct?
A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only
34 One mole of
A Nylon each
and alkaneare
Terylene undergoes complete combustion.
both polyesters.
34 Which
An alkane
B Proteins
ester will
is and produce
nylon
produced byseven
have the molestogether
same
reacting of products?
monomer units.carboxylic acid HCO2H and the alcohol
the
CH3CH2CH2OH.
C CH
A Proteins
4 have theB same
C2Hamide
6 linkages
C asC3nylon.
H8 D C4H10
What is the name
D Terylene and are
and fats structure
estersofbut
this ester?
with different linkages.
35 Ethanoic acid is formed when ethanol is reacted with acidified potassium manganate(VII).
name structure
What
A
is the name of this process? CH CH CO CH
methyl propanoate 3 2 2 3
A B combustion
methyl propanoate HCO2CH2CH2CH3
B C condensation
propyl methanoate CH3CH2CO2CH3
C D oxidation
propyl methanoate HCO2CH2CH2CH3
D
© UCLES 2017
polymerisation 5070/11/M/J/17 [Turn over
CH3–CH2–CH2–CH2–OH
37 After
© UCLES which conversion does the product contain
2017 more carbon atoms than the reactant?
5070/11/M/J/17
36 When the alcohol of molecular formula C4H10O is oxidised, what is the molecular formula of the
acid formed? 15
A C4H12O2 B C4H10O2 C C4H8O2 D C4H6O2
20 2017 WIN P12 Q37
37 The diagrams show the structures of five hydrocarbons.
alt
1 2 3
H H H H H H H H H
H C C C C C H H C H H C C C H
H H
H H H H H H C C C H H H
H C H
H 13 H
H C H H
34 Which pair of gases are both non-acidic?
H
A ammonia and methane
B 4
carbon dioxide and ammonia 5
C H dioxide
methane and nitrogen H H H H H H
D nitrogen dioxideHandCcarbon
C dioxide
C C H H C C C H
H H H H H
H C the
35 Which term correctly describes H conversion of seawater into
H drinkable
C H water?
A chlorination H H
B desalination
Which three hydrocarbons are isomers of each other?
C
A filtration
1, 2 and 4 B 2, 3 and 5 C 2, 3 and 4 D 3, 4 and 5
D neutralisation
38 2018
21 WhichSUM P11
alcohol andQ36
acid will react together to make the ester CH3COOC2H5?
36 Which formula represents an alkane?
A CH3OH and CH3COOH
A
B C31HOH
CH 33 and C HBCOOH
C31H60 C C31H62 D C31H64
3 2 5
13
C C2H5OH and CH3COOH 13
36 Z
37
22 Which diagram shows
is a compound that: a branched-chain isomer of butane?
D C2H5OH and C2H5COOH
2018
36 SUM
Which P12
A diagram
can beQ36
shows a branched-chain isomer of butane?C
B only other
formed, as the product, when the alkane C8H18 is Dcracked to
H H AH produce butaneH B H H C D
H
decolourisesH bromine
C HH water
H C HC HC HH H C HH H C HH
H
HH H H C H
H C C C H H C has a branchedH C
chain H H C
structure.
C H H H C H
H H H C H
H C C H CH H
H HisCtheHformula
What of Z? H H C C H H
H H H C C H
H C H H C C C H
AH HB H HC H H H CD
H
C H
H H H H H C H
H H H H H H H H H
H H H C HH
H
C C C H H C C C H H C C C H C HC C H
© UCLES 2017 5070/12/O/N/17 [Turn over
H A straight-chain
37 H alkene, C4H H
H8, undergoes an addition H H bromine. H
H with
reaction H
37 A straight-chain alkene, H
C4H8C H
, undergoes an addition reaction with bromine. H C H
What is the possible structure of the product?
What is the possible structureHof the product? H
A CH3CHBrCH2CH2Br
B ACHCH3CHBrCH2CH2Br
3CHBrCHBrCH3
C BCHCH 3CHBrCHBrCH3
2BrCH2CH2CH2Br
alt
C solids harmful microbes unpleasant odours
C2H4 C3H8 C4H10 C5H10 CH
and tastes 6 14
AD 1 solids B 2unpleasantCodours
3 harmfulDmicrobes
4
and tastes
11
35 2018
24 The diagram
WIN P12shows the structural formula of an organic compound.
Q34
32 River water contains many impurities.
34 Which statement about the homologous series of alkanes is correct?
H H
A Alkanes are unsaturated hydrocarbons.C from river
Which process alone can produce pure water H water?
BA Alkanes
adding chlorine
all have the general formula
H CCnH2nC. C H
B
C distillation
The boiling points decrease as the number of carbon atoms per molecule increases.
H H H
DC The
filtering
liquid alkanes become more viscous as the mass of the molecules increases.
Which statement about this compound is correct?
D passing through carbon
A It iscompound
35 2019 a saturated hydrocarbon.
25 Which SUM P11 Q33
has the empirical formula with the greatest relative formula mass?
B
33 A It isH an alkene.
Compound
C Q is a hydrocarbon
B C4H10 that has C
no isomers.
C5H10 Compound
D Q C6does
H6 not decolourise bromine
2 6
in the dark.
C It is an isomer of butane.
Which
36 Which
D compound
statement
It will could
undergoabout be Q?
vegetable
addition oil and the margarine made from it is correct?
with hydrogen.
A
A C3H6 are liquids at
Both B room
C3Htemperature.
8 C C4H8 D C4H10
37 When ethene
35UCLES
When reacts with steam to form ethanol, which type of reaction takes place?
© 2018a
molecule of a saturated hydrocarbon is cracked, it forms
5070/11/O/N/18 two molecules X and Y.
A addition
Which row is correct?
B fermentation
X Y
C polymerisation
D A reduction
H2 CnH2n
B H2 CnH2n+2
C H2O CnH2n
D H2O CnH2n+2
alt
Structures 1, 2, 3 and 4 are saturated hydrocarbons.
1 2
H
H C H H H H H H
H H H H C C C C C H
H C C C C H H H H H
H H H H C H
H C H H
H
3 4
H
H H
H H H C H
C C H H H H
H H
C C H C C C C C H
H H
C C H H H H
H H
H H H C H
12
27 2019 WIN P12 Q33
33 Alkanes are saturated compounds containing carbon and hydrogen only.
alt
Structures 1, 2, 3 and 4 are saturated hydrocarbons.
1 2
H
H C H H H H H H
H H H H C C C C C H
H C C C C H H H H H
H H H H C H
H C H H
H
3 4
H
H H
H H H C H
C C H H H H
H H
C C H C C C C C H
H H
C C H H H H
H H
H H H C H
Answers
1 A
alt
C 27
2 D
3 C
4 A
5 C
6 B
7 C
8 B
9 D
10 D
11 C
12 C
13 B
14 C
15 D
16 D
17 B
18 C
19 C
20 A
21 D
22 A
23 C
24 D
25 B
26 A
Alkenes
13
WS
38 Which diagram shows the structure of an alloy?
alt
10
1 2014 WIN P12 Q32
A B
32 Which row is correct for the reaction of the alkene with steam and a catalyst?
alkene product
C D
12
2 2014
33 WIN
Why is P12used
carbon Q38in water purification?
38 When butene reacts with bromine, which compound could be made?
A It acts as a filter to remove insoluble solids.
B A
It desalinates the water. B
C Br water.
It disinfects the H H H Br Br H H
Br Hreact
39 Hydrogen and nitrogen H to form
H ammonia. H H H H
34 Which of the statements about the preparation and properties of ammonia is correct?
N2 + 3H2 2NH3
A Ammonia is formed when ammonium chloride is heated with an acid.
Which statement C
is correct? D
B Ammonia reacts with sodium hydroxide solution to form a salt and water.
A Br Hin industry
Br H the Contact process. Br H H Br
C Ammonia
Ammonia isreacts
made with water tobyform hydrogen ions.
B
D Ammonia
A solution Cammonia
H isofused C Cin water
in industryCto make
H ahydrogen
has and
pH greater than 7.C C
Hnitrogen. C C H
C Hydrogen, forHthe H H reaction,
forward H H H
is obtained from cracking oil. H H
D Weed killers are manufactured from ammonia.
3 2015
39 WIN
Methane is P11 Q40
the first member of the alkane series of hydrocarbons. The second member is ethane.
40 Which statement about the hydrocarbon C2H4 is not correct?
Which statements about ethane are correct?
A It contains a double bond.
1 Ethane has the formula C2H4.
B It decolourises bromine water.
2 Ethane has a higher boiling point than that of methane.
C It forms a condensation polymer.
3 Ethane has the same molecular formula as methane.
D It forms an alcohol when reacted with steam.
4 Ethane has chemical properties very similar to those of methane.
40 When ethanol reacts with ethanoic acid, the ester ethyl ethanoate is formed.
What is the formula of the ester formed when methanol reacts with butanoic acid, C3H7CO2H?
A C H5CO2C2H5
© UCLES 20152 5070/11/O/N/15
Alkenes
B WS
C3H7CO2C2H5 Abul Fazal
C 2014
© UCLES CH3CO2C3H7 5070/12/O/N/14
5 10 2
alt
H H H H H H H
A by polymerisation reactions H O
C B C by the addition
H Cof hydrogen
C C to unsaturated C C oils
H vegetable H C C C H
H O H
Cl C H by the combustion
H of alkanes H H H H
D by the cracking of hydrocarbons
A 1 B 2 C 3 D 4
2016
©5UCLES 2016SUM P12 Q35 5070/11/M/J/16
35 Which statements are correct for alkenes but not for alkanes?
1515
6 2016 SUM P12 Q40
40 40The structures
The of of
structures four hydrocarbons,
four W,W,
hydrocarbons, X,X,
YY and Z,Z,
and are shown.
are shown.
WW XX YY ZZ
© UCLES 2016 5070/12/M/J/16
H H HH HH H H HH HH HH HH HH HH HH HH
H HC C C C C C H H H H C C C C CC CC HH HH CC CC CC CC CC CC HH
H H HH H H HH HH HH HH HH HH HH
H HC C H H H H C C HH
HH HH
Which
Whichrowrow
is correct?
is correct?
isomers of of
isomers decolourise
decolourise branched
branched
each other
each other bromine
bromine structures
structures
A A WW
and X X
and Y and ZZ
Y and WW
and YY
and
B B WW and
and X X Y and
Y and ZZ XX and
and ZZ
C C Y and
Y and Z Z WW and
and YY XX and
and ZZ
D D Y and
Y and Z Z WW and
and ZZ WW and
and YY
A 1 B 2H H C HC 3 H DC 4H H
7 2016 WIN P11 Q35
H C C C
C H
alt
35 With which substance will ethene react to form more than one product?
H H C H H C H H
A argon
H H
B hydrogen
X Y
C oxygen
Two steam
D students make the following statements.
H H
X Y
37 The diagram shows the structure of an ester.
© UCLES 2016 5070/11/O/N/16
H H H
Two students make the following statements. O
H C C C C H H H
Student 1 Hydrocarbon X is an isomer of Y.
O C C C H
H H XHis unsaturated
Student 2 Hydrocarbon but Y is saturated.
H H H
Which students are correct?
What is the name of this ester?
A both 1 and 2
A
B butyl
1 onlybutanoate
B
C butyl
2 onlypropanoate
C
D propyl
neitherbutanoate
1 nor 2
D propyl propanoate
9 2016
37 WIN P11
The diagram Q38
shows the structure of an ester.
H H H
38 An unsaturated hydrocarbon with six carbon atoms contains only three C=C double bonds. This
hydrocarbon is reacted with excess hydrogen atOa high temperature.
H C C C C H H H
What is the formula of the resulting hydrocarbon?
O C C C H
A C6H8 B C6H10H H HC C6H14 D C6H16
H H H
What
© UCLES is
2016 the name of this ester? 5070/11/O/N/16 [Turn over
A butyl butanoate
B butyl propanoate
C propyl butanoate
D propyl propanoate
C
A oxygen
1 B 2 C 3 D 4
10 2016 WIN P12 Q37
D steam
37 With which substance will ethene react to form more than one product?
alt
38 Which statement about isomers of a compound is always correct?
A argon
13
A
B They have different empirical formulae.
hydrogen
35 The repeat unit of a polymer is shown.
B
C They have different relative molecular masses.
oxygen
C steam
They have only carbon and hydrogen in CH 3 Clmolecules.
their
D
D C
They have the same molecular formula. C
38 2016
11 WhichWIN
statement about isomers of a compound
P12 Q39 H isBralways correct?
39 How manyhave
A They of the structures
different show formulae.
empirical an unsaturated hydrocarbon molecule?
Which monomer would produce this polymer?
B They have different relative molecular masses. O
A B C D
CO They
C have
O only CH CH
carbon
3 and
2 CH
hydrogen
2 CH
in 3their CH CH
molecules.
3 CH 2 CH3 C
H Cl CH3 H CH3 H Cl CH3
D They have the same molecular formula. O H
C C C C C C C C
A 1 B 2 C 3 D 4
39 How many of
CHthe structures show
3 Br Clan unsaturated
Br hydrocarbon
Br Cl molecule?
H Br
A 1 X C9H20 B 2 C 3 D 4
Y C10H20
Z C10H22
33 CFC compounds were used as aerosol propellants. The structure of one CFC compound is
shown.
24
F
Cl
13
13 2017 SUM P12 Q38 F C C H
38 Molecules 1–4 are unbranched hydrocarbons.
alt
F H
1 C10H22
Which element in this compound causes a depletion of ozone in the atmosphere?
2 C10H20
A carbon
3 C9H20
B chlorine
4 C8H16
C fluorine
Which row correctly identifies these hydrocarbons as alkanes or alkenes?
D hydrogen
alkane alkene
34 What
A is removed
1 and 2or destroyed when
3 and 4 water is desalinated to make it drinkable?
A B bad odours
1 and 3 2 and 4
B C harmful bacteria
1 and 4 2 and 3
C D sodium chloride
2 and 3 1 and 4
D solid particles
39 2017
14 WhichWIN P11contains
polymer Q35 only three different elements?
35 Compounds S and T both contain two elements only. The compounds have the following
A protein
properties.
B poly(ethene)
They both burn in air to form carbon dioxide and water only.
C poly(propene)
They both react with chlorine by substitution.
D starch
S has a higher boiling point than T.
What could
40 Which compounds
statement S and T be?
about macromolecules is correct?
13
15 2017 WIN P11 Q36
36 Which row correctly describes alkenes?
A CnH2n+2 no change
© UCLES 2017 5070/11/O/N/17
B CnH2n+2 the aqueous bromine is decolourised
C CnH2n no change
D CnH2n the aqueous bromine is decolourised
36 36Which
Which formula
formula represents
represents anan alkane?
alkane?
25
H3133H33
A AC31C B B C31CH3160H60 C C C31CH3162H62 D D C31
CH H64
3164
alt
cancan
be be formed,
formed, asas
thethe only
only otherproduct,
other product,when
whenthe
thealkane
alkaneC8CH818
H18is iscracked
crackedtoto
produce
produce butane
butane
decolourises
decolourises bromine
bromine water
water 13
hashas a branched
a branched chain
chain structure.
structure.
36 Which diagram shows a branched-chain isomer of butane?
What
What is the
is the formula
formula of Z?
of Z?
A B 11 C D
H AH H A H B B H H C C DD
32 River water contains many impurities. H
H C H CH H CH H H CH H HH HC H H HC H
H
H H H H H HH HH HH HH
Which process alone can produce pure water from river water? H H H C H
H C C H H
C HC C C C HC H H H H C C C C C C H H H H C C C C C C H H C C C C CC HH
A adding chlorine H C C C H
H H C HH HH HH HH C CH H
H H
B distillation H H H H HH HH H H
H H C H H H H H C H
H C H H C H
C filtering H C H
H H
D passing through carbon H H
H
34 C CH2organic
Which BrCH2CH 2CH2Br
compound requires the least number of moles of oxygen for the complete
©Dcombustion
UCLES 2018 of one mole of the compound? 5070/11/M/J/18 [Turn over
CH
© UCLES 2018 3
CH2CH2CH2Br 5070/11/M/J/18 [Turn over
A C3H7OH B C3H7COOH C C3H8 D C4H8
X Y
A H2 CnH2n
B H2 CnH2n+2
C H2O CnH2n
D H2O CnH2n+2
alt
bonds.
7 Hydrogen sulfide burns in an excess of oxygen according to the equation shown.
Which statement about compound Q is correct?
2H2S(g) + 3O2(g) 2H2O(g) + 2SO2(g)
A It can be polymerised.
48 dm3 of hydrogen sulfide is burned.
B It decolourises bromine water.
Which volume of sulfur dioxide will be formed at room temperature and pressure?
C It has three isomers.
[All volumes are measured at the same temperature and pressure.]
D It reacts with chlorine by substitution.
A 24 dm3 B 36 dm3 C 48 dm3 D 96 dm3
34 2019
20 WhichWIN P11 Q08
organic compound requires the least number of moles of oxygen for the complete
8 combustion of one mole
Which row correctly of thethe
identifies compound?
different formulae of ethene and of its homologous series?
A C3H7OH B C3H7COOH C C3H8 D C4H8
CH2 C2H4 CnH2n
A B
Br H H H Br Br H H
H C C C C H H C C C C H
© UCLES 2019 5070/11/O/N/19
Br H H H H H H H
C D
Br H Br H Br H H Br
H C C C C H H C C C C H
H H H H H H H H
35 How many structural isomers with the formula C4H10O are alcohols?
A 2 B 3 C 4 D 5
What is Z? 27
A CO B N2 C H2O D NO2
22 2019 WIN P12 Q32
32 A student investigates the properties of a colourless organic liquid.
alt
Which observation shows that the liquid is unsaturated?
13
23 2019 WIN P12 Q34 13
34 When butene reacts with bromine, which compound could be made?
34 When butene reacts with bromine, which compound could be made?
A B
A B
Br H H H Br Br H H
Br H H H Br Br H H
H C C C C H H C C C C H
H C C C C H H C C C C H
Br H H H H H H H
Br H H H H H H H
C D
C D
Br H Br H Br H H Br
Br H Br H Br H H Br
H C C C C H H C C C C H
H C C C C H H C C C C H
H H H H H H H H
H H H H H H H H
35 2019
24 WhichWIN P12 Q35
statement about propene is correct?
35 Which statement about propene is correct?
A It can be formed by cracking butane.
A It can be formed by cracking butane.
B It has the formula C3H8.
B It has the formula C3H8.
C It is a saturated hydrocarbon.
C It is a saturated hydrocarbon.
D It reacts with hydrogen to form ethane.
D It reacts with hydrogen to form ethane.
Answers
1
alt
C
2 B
3 C
4 D
5 B
6 A
7 C
8 D
9 C
10 C
11 A
12 A
13 B
14 C
15 D
16 D
17 B
18 A
19 D
20 A
21 B
22 A
23 B
24 A
29
A carbon, hydrogen and oxygen
B carbon, hydrogen and nitrogen
C carbon, hydrogen and sulfur Alcohols WS
alt
D carbon, nitrogen and oxygen
1 2014 SUM P11 Q40
40 The structural formulae of some organic compounds are shown below.
H H H
H H H
H C C C H
H C C C O H
H O H
H H H
H
1 2
H H H H H O
H O C C C O H H C C C O H
H H H H H
3 4
A 1 only
B 1 and 2 only
C 1, 2 and 3
D 4
alt
H H H
H H H
H C C C H
H C C C O H
H O H
H H H
H
1 2
H H H H H O
H O C C C O H H C C C O H
H H H 11 H H
3
33 Two esters have the same molecular formula, C3H6O2. 4
What are the names of these two esters?
Which compounds are alcohols?
A 1
1 only methyl ethanoate
B 2 2 only
1 and ethyl propanoate
C 3 3
1, 2 and ethyl methanoate
D 4 4 propyl methanoate
O
A Carboxylic acids contain the functional group C .
H
B 2014
© UCLES Ethanoic acid will react and fizz when5070/12/M/J/14
copper is added. [Turn over
35 When cracked, one mole of a compound, X, produces one mole of propene and one mole of
hydrogen.
X → C3H6 + H2
A an alcohol
B an alkane
Alcohols WS Abul Fazal
C an alkene
D a carboxylic acid
A Alkanes are readily polymerised.
A
B clay particles
Alkanes react with bromine by addition.
B
C 31
microbesreact with chlorine by substitution.
Alkanes
C
D nitrates has three more carbon atoms and eight more hydrogen atoms than methane.
Butane
4 2015 13
D SUM P12 Q35
odours
37
35 The structures of three
abouthydrocarbons from the same homologous seriesisare shown.
alt
Which statement members of the homologous series of alcohols correct?
32 Which property of a liquid ester can be used to check its purity before use as a food flavouring?
H
A An alcohol with two carbon atoms in each molecule is called methanol.
A boiling point
H C H
B Butanol can be combusted to give carbon dioxide and water only.
C Ethanol isHthe only alcohol that can
B colour H be H oxidised
H to a carboxylic Hacid. H
H C H made by the
H catalysed
C C addition
C H of steam H C C C H
C
D smell
Propanol can be to ethene.
D solubility in water
H H H H H H H
5 2015
36 When WIN P11one
cracked, Q33mole of a compound, X, produces one mole of propene and one mole of
W X Y
33 hydrogen.
Which alcohol will, on oxidation, produce CH3CH2CO2H?
Which
A CHstatement
3OH
is correct? X → C3H6 + H2
A
B All
CH
What three
3CH
type molecules
compoundare
of2OH unsaturated hydrocarbons.
is X?
B
C
A All
CHthree
an molecules
3CH2CH
alcohol 2OH have the same empirical formula.
C
D
B W has
HOCH
an the lowest boiling point.
2CH2CH2OH
alkane
D
C X
anisalkene
an isomer of Y.
6 2015 WIN P12 acid
D a carboxylic Q38
38 How many of the following statements about ethanol are correct?
6 used as a solvent
A 3 B 4 C 5 D 6
A B C D
H O O O
O N C N C O C O N
© UCLES 2015
H 5070/12/M/J/15
H
12
7 2016 SUM P11 Q34
34 Which statements about alcohols are correct?
alt
1 All alcohols contain the hydroxide ion, OH–.
2 Ethanol can be formed from ethene using a reaction catalysed by yeast.
3 Methanol can be oxidised to methanoic acid.
4 The alcohols X and Y shown are isomers.
X Y
H H H H H H H H
H C C C C H H C C C C H
H O H H H H H O
H H
35 C
Ethanoic acid is
proteins
1 formed when ethanol
2 is reacted with acidified potassium manganate(VII).
D sugars
What
A is theoxidised
name of this process?
CH3COOH
A B combustion
oxidised CH3CH2COOH
36 Ethanol, C2H6O, was reacted with propanoic acid, C3H6O2, in the presence of concentrated
B C condensation
sulfuric reduced
acid. CH3COOH
C D oxidation
Which
reduced CH3CH2COOH
statement about the organic product of this reaction is correct?
D Itpolymerisation
A has the formula C5H10O2.
9 2017
37
SUM P12 Q36
Polymer Z has the structure shown.
B It has the formula C5H12O3.
O
36 The structure of compound XOis shown. O O
C It is formed by an addition reaction.
C C NCH3–CH2N –CH2C–CH2–OHC N N
D It is propyl ethanoate.
Which statement is not correct? H H H H
A
37 How Xcan
These isfour
an alcohol
alkenes
terms
bebecause it contains
manufactured?
can be used an polymers.
to describe –OH group.
B
A X ispolymerisation
by an
1 isomer of propanol.
addition
reactions
polymer
C
B X would
by
2 burn
the additioninofair to form
hydrogen
condensation carbon dioxide and
to unsaturated
polymer water. oils
vegetable
D
C X would
by
3 have a higher
the combustion
polyamide boiling point than ethanol.
of alkanes
D by the cracking of hydrocarbons
4 polyester
37 After which conversion does the product contain more carbon atoms than the reactant?
Which
© UCLES 2016 two terms can be applied to polymer Z?
5070/11/M/J/16
A ethanol to ethanoic acid
A 1 and 3 B 1 and 4 C 2 and 3 D 2 and 4
B ethanol to ethyl ethanoate
Alcohols WS
C ethene to ethane Abul Fazal
D ethene to ethanol
A CnH2n+2 no change
Which
B impurities can
CnH2n+2 be removed by which treatment?
the aqueous bromine is decolourised
C C nH2n
filtration no33
change
use of carbon chlorination
D
A CnHmicrobes
harmful 2n the aqueous bromine is decolourised
solids unpleasant odours
10 2017 WIN P11 Q37 and tastes
harmful
B table
37 The microbes
contains statementsunpleasant odours by which ethanol
about processes solids is produced on a large scale
alt
from ethene and from glucose. and tastes
C solids harmful microbes unpleasant odours
from ethene from
and glucose
tastes
D 1 solids reactionunpleasant
is faster atodours reaction
harmful is faster at
microbes
and
300 °C than at tastes
200 °C 100 °C than at 30 °C
2 produces pure ethanol
produces a dilute aqueous
solution of ethanol
34 Which statement about the homologous series of alkanes is correct?
3 uses a catalyst uses a catalyst
A Alkanes are unsaturated hydrocarbons.
4 uses steam produces carbon dioxide
B Alkanes all have the general formula CnH2n.
Which rows are correct?
C The boiling points decrease as the number of carbon atoms per molecule increases.
A 1, 2 and 3 B 1 and 4 133 and 4
C 2, D 2 and 3 only
D The liquid alkanes become more viscous as the mass of the molecules increases.
36 Which statement about vegetable oil and the margarine made from it is correct?
13
38
11
35 2017
Which WIN P12
The structure
compound Q36
of an ester is shown.
has the empirical formula with the greatest relative formula mass?
A Both are liquids at room temperature.
36 When the alcohol of molecular formula C4H10O is oxidised, what is the molecular formula of the
O C CH H H H
A
BacidC2H6 occur naturally.
formed?
Both B C4H10 5 10 D C6H6
CA Margarine
C4H12O2 has the B higher H C point.
C4H10melting
O O
C C CH O C C HD C H O
2 4 8 2 4 6 2
36 Which statement about vegetable oil and the margarine made from it is correct?
D Vegetable oil has fewer carbon-carbon double H Hbonds
H than margarine.
37 AThe Both are liquids
diagrams at room
show the temperature.
structures of five hydrocarbons.
12 2018 WIN
What is the P11
nameQ37 of this ester?
37 B Both
Which occur
group naturally.
is 1found in alcohols? 2 3
A ethyl propanoate
C
A Margarine
C=C has the
B higher
CO Hmelting point.
C CONH D OH
H H propanoate
B methyl H H H 2 H H H H
D Vegetable oil has fewer carbon-carbon double bonds than margarine.
H C Cethanoate
C propyl C C C H H C H H C C C H
38
13 An ester is formed
2018 WIN P12 Q37 from a carboxylic acid H
and H
an alcohol.
37 D propyl
When Hmethanoate
Hethene H Hwith Hsteam to form
reacts H H
How does the number of carbon, hydrogen H ethanol,
C andwhich type
C oxygen of reaction takes place?
C atoms
H in an ester
H Cdiffer
H from the total
number
A of these atoms in the carboxylic acid
addition H and alcoholH from which the ester is formed?
H C H H
B fermentation
carbon atoms hydrogen atoms oxygen atoms
H
C A polymerisation
fewer fewer fewer
D B reduction 4 5
fewer same fewer
C same H H H
fewer H fewer H H H
© UCLES 2017 5070/11/O/N/17 [Turn over
D same H C C C
same C H same H C C C H
H H H H H
H composition
39 Which statement about the C H H C
of polymers is correct? H
© UCLES 2018 5070/12/O/N/18 [Turn over
A H
Nylon contains oxygen atoms but not nitrogen atoms. H
Which
B three hydrocarbons
Proteins are isomers
contain both nitrogen of and
atoms eachoxygen
other? atoms.
C
A Terylene
1, 2 and 4contains
B nitrogen atoms.
2, 3 and 5 C 2, 3 and 4 D 3, 4 and 5
D The polymer used to make clingfilm contains oxygen atoms.
38 Which alcohol and acid will react together to make the ester CH3COOC2H5?
alt
named correctly. Br H A H H Br BrB H H
H CBr CHCC Br C H H H C Br H D
C H C BrC H
Which structures are correctly named?
H C Br C H C Br C H H H C Br CH C H C Br H
A P, Q and R H BH P H only H C Q only HD HR only
H H
H C H C H C H C H H H C H C H C H C H H
35 Which
37 2019
15 statement
WIN
What is about
H
P11 Q35
the empirical Hpropene
formula is correct?
H of H
ethanoic acid? H H H H
35 AHowItmany
can structural by
isomers with the formula C4H10O are alcohols?
A CH 2Obe formedB cracking
CH4O butane.C C2H 3O D C2H4O2
35 BHow many structural
A It2 has the formula isomers
BC H 3 . with the formula C H
C 4 4 10 O are alcohols?
D 5
3 8
38 C
What
A It2 is
is the structurehydrocarbon.
a saturated Bof propyl
3 methanoate?C 4 D 5
36 Which
16 2019 statements
WIN P11 about the alcohol CH CH CH OH are correct?
with Q36
3 2 2
A ItCH
D 3COOCH
reacts CH2CH3 to form ethane.
2hydrogen
36 Which statements
1 When2aboutCH33CHthe2CH
alcohol CH3CH2CH2OH are correct?
2OH is oxidised, it forms propanoic acid.
B CH3COOCCH CH
36 Which 1 describes
2
C CHterm When
CH 3CH
3CH2COOCH
CH
23CH3CH
2OH
the 2CH 2OH of
burns
structure is Terylene?
in oxidised,
the it forms
air to form propanoic
carbon dioxideacid.
and water.
A
D 2
3 2CH
polyalkene
CH3CH CH2CH2OH burns
CH23OOCH can beinformed
the air by
to the
formaddition
carbon reaction
dioxide and water.ethene and steam.
between
BA polyamide
1 and CH3CHB
3 2 only 2CH21OH andcan be formed
3 only C by the addition
2 and 3 only reaction
D 1, 2between
and 3 ethene and steam.
39 CWhich substance,
A polyester
1 and 2 only onBcombustion,
1 and 3 onlyproduces
C oxides
2 and 3ofonly
nitrogen?
D 1, 2 and 3
37 DPropanoic
A fat
protein acid reacts with calcium carbonate. The products of this reaction are
calcium propanoate, carbon dioxide and water.
37
17 Propanoic
2019
B WIN P12
protein acid Q37
reacts with calcium carbonate. The products of this reaction are
calcium propanoate,
What is the equation carbon
for this dioxide and water.
reaction?
37 Which process is involved in the formation of ethanol from ethene?
C starch
What is2H
the
A addition
2C equation for this reaction?
5COOH + Ca2CO3 2C2H5COOCa + CO2 + H2O
AD Terylene
BA 2C2H5COOH + Ca
B combustion 2CO
CaCO 33 2C
(C 2H
2H 5COOCa
5COO) 2Ca + + CO
CO22 ++ H
H22O
O
CB
C polymerisation CaCO
2C23H57COOH + Ca 2CO33 (C2H
2C 5COO)
3H 2Ca +
7COOCa + CO
CO22 ++ H
H22O
O
C substitution
DD 2C3H7COOH + Ca 2CO
CaCO 33 2C
(C 3H
3H 7COOCa
7COO) 2Ca +
+ CO
CO22 ++ H
H22O
O
D 2C3H7COOH + CaCO3 (C3H7COO)2Ca + CO2 + H2O
14
18 2019 WIN P12 Q38
38 Which compound is an alcohol?
alt
A B
H H H H H H H H
H C C C C H H C C C C H
H O H H H O O H
CH3 H H
C D
H H O H H O H
H C C C O H H C C C C H
H H H H H
A CH3CH2CH2COOCH3
B CH3CH2CH2CH2CH2OH
C CH3CH2CH2CH2COOH
D CH3CHCHCH2CH3
Answers
1
alt
C
2 C
3 C
4 B
5 C
6 C
7 D
8 A
9 B
10 C
11 C
12 D
13 A
14 C
15 C
16 A
17 A
18 B
Carboxylic Acids WS
36
A Which
Propane has a higher boiling point than hexane.
C lightPropane has a higher boiling point than hexane.
B A Propane has a higher relative molecular mass 12 than hexane.
alt
D water
C B Propane
Propane has has
morea higher relative
isomers molecular mass than hexane.
than hexane.
1 2014 SUM
33 Which P11
compound, Q33
on combustion, never forms carbon?
D C Propane
Propane has more
is more isomers
flammable thanthan hexane.
hexane.
33 A liquid
carbonreacts with each of sodium carbonate, potassium hydroxide and ethanol.
monoxide
D Propane is more flammable than hexane.
37 B
Whatethanol
When isa the liquid?
volcano erupts, which gas is produced in significant amounts?
C
37
A ethene
When a volcano
aqueous ammoniaerupts, which gas is produced in significant amounts?
A carbon monoxide
D
B methane
A carbon
ethanoic monoxide
acid
B methane
C B
C ethylmethane
ozone ethanoate
34 Which process is an example of cracking?
D C
D
ozone
sodium
sulfur hydroxide
dioxide
A DC2Hsulfur
4 + Hdioxide
2O → C2H5OH
2 B
38 3H6 + H2 →
FourCcompounds areCshown.
3H8
2014C3SUM
O P11
+ 5O2 Q38
38 Four
H8 compounds → are shown.
O H
© UCLES
C 2014 5070/11/M/J/14
H
3CO 2 + 4H2O
H O H O H
HH → O C H + C2H6 H O H O H O H
H C C4 10 H 2 H4 C C H
D C
H C C C H C C H
H C C H H C C H
O C C H H C C C H C C H H O H
H H H
isO H H H O
H
35 A hydride C C containing
a compound H H
only two elements, one of which is hydrogen. H
H H H
H H
H form 2
H the greatest number 3 4
1
Which element can of different hydrides?
2 3 4
A carbon 1
Which pair of compounds have the same empirical formula?
B Which
chlorinepair of compounds have the same empirical formula?
A 1 and 2 B 1 and 3 C 2 and 3 D 2 and 4
C A nitrogen
1 and 2 B 1 and 3 C 2 and 3 D 2 and 4
D oxygen
3 2014 SUM P12 Q36
© UCLES 2014 5070/11/M/J/14 [Turn over
36 ©AUCLES
liquid2014
reacts with each of sodium carbonate, potassium hydroxide and ethanol.
5070/11/M/J/14 [Turn over
A aqueous ammonia
B ethanoic acid
C ethyl ethanoate
D sodium hydroxide
alt
37 Which statements would be true of the compound which has the formula shown?
O H O
H O C C C O H
11
5 2015 WIN P11 Q34
34 The diagram shows the structure of an organic acid.
H H O
© UCLES 2014 5070/12/O/N/14 [Turn over
H C C C
H H O H
38 Which
A statement
butanoic about
acid alkanes is correct?
no
A B Ethane
butanoic
reactsacid addition13
with chlorine in anyes reaction.
34 BThe table
C Propaneshows
has some
propanoicaacid atmospheric
higher pollutants and their possible effects.
no than butane.
boiling point
CWhich
D Therow is not correct?
propanoic
molecule acid
of the alkane that yes
contains 99 carbon atoms has 200 hydrogen atoms.
D There are three isomers with the formula C4H10.
pollutant effect
2016 SUM P11 Q39
6 A carbohydrate such as starch can be represented as shown.
35
A statement
CFCs causeacid
depletion of the ozone layer
X X X X
39 Which about ethanoic is correct?
B CO2 forms photochemical smog
A Ethanoic acid can be made by the catalysed addition of steam to ethene.
C is X? CO
What is poisonous to humans
B Propanoic acid can react with ethanoic acid to produce an ester.
A D carbon NO2 forms acid rain
C Solutions of 1.0 mol / dm3 ethanoic acid and 1.0 mol / dm3 hydrochloric acid will react with
B magnesium
hydrogen at equal rates.
35 D
CWhich compound
formula ofisethanoic
nitrogen
The the mostacid
viscous
is CHand the least flammable?
3CO2H.
C6H14
DA oxygen B C8H18 C C10H22 D C12H26
7 2016
40 WIN
Polymer P12
Z has theQ36
structure shown.
36 How many moles of ethanoic acid, CH3CO2H, react with one mole of magnesium?
O O O O
A 1 B 2 C 3 D 4
C C N N C C N N
H H H H
37 With which substance will ethene react to form more than one product?
Carboxylic Acids WS Abul Fazal
A argon
These four terms can be used to describe polymers.
B hydrogen
1 addition polymer
39
14
8 2017 SUM P11 Q39
39 An organic compound, X, has a molecular formula C4H8O2 and turns damp, blue litmus paper red.
alt
What is the structure of X?
A B
H H O H H O H H
H C C C O C H H C C O C C H
H H H H H H
C D
O H H H 12 O H H H
H of each
34 One mole C O C undergoes
alkane C C complete
H H O
combustion. C C C C H
H H H H H H
Which alkane will produce seven moles of products?
A
Which statement is not correct? B
H
O it contains O
A X is an alcohol because an –OH group.
H H C H
B C
X is an isomer of propanol. C H
H in C O C H
C X would burn air toOform carbon
H dioxide and water.
D X would have a H
higher boiling point than ethanol. H
14
11 2017 WIN P12 Q39
39 Which compound has a pH of less than 7 in aqueous solution?
alt
A B
O H O
H H C H
C C H
H C O O C H
H
H H
C D
O H O
H C H C C H H
O H O C C H
H
H H
40 2018
WhichSUM
statement 14
12 P12 about
Q38 polymers is correct?
38 The
A diagram shows
Nylon and the structure
Terylene of oxalic
are produced acid. polymerisation.
by addition
B Nylon and Terylene both contain theOamide linkage.
O
C Simple sugars can be produced by hydrolysing
C C proteins.
D Starch contains the elements carbon,
H O hydrogenOandHoxygen.
oxalic acid
A B
H H H H H
H C C O H H C C C H
H H H O H
C D
H H H H H H
H O C C O H H O C C C C O H
H H H H H H
Carboxylic Acids WS It reacts with sodium hydroxide to produce a salt. Abul Fazal
alt
C
B
A the
CH2manufacture
making
O ethene and A
Bof margarine
hydrogen
CH4O from butane
from aCvegetable
C2H3O oil D CB
2H4O2
D the manufacture
C Br ofH margarine
reaction between H
etheneHand
fromoxygen, carbonBr
givingoil
a vegetable Br and
dioxide H water
H
38 Whatthe
2019 is
SUM the structure of propyl methanoate?
14 D HP12between
reaction CQ36 C ethene
C CandHoxygen, giving carbonH Cdioxide
C and
C water
C H
36 Two
A CH equations
3COOCH involving
2CH 2 CH ethanol
3
are shown.
Br H H H H H H H
36 Two
B CH equations
3COOCCH involving
2CH ethanol are shown.
oxidation
1 ethanol +3 oxygen carboxylic acid
C CH3CH2COOCH3 oxidation
1 ethanol + fermentation
oxygen carboxylic acid
2 CH glucose C ethanol + carbon dioxide D
D CH3CH 2 2OOCH
Br Hfermentation
2 is glucose Br H Br H
ethanol + carbon dioxide H Br
Which row correct?
39 Which substance,Con combustion, C produces oxides of nitrogen?
Which row isHcorrect? C C H H C C C C H
molecular formula of
A fat carboxylicH acidHin 1H aHcatalyst is needed H H H H
molecular formula of
B protein a catalyst is needed
A carboxylic
CH3CO acid
2H in 1 1 only
35 C B starch
How many structural
C isomers with the formula C4H10O are alcohols?
A 2H35CO
CH CO22H H 1 only
D
ABC Terylene
2
2 CCH
5 CO2B
H3CO2
HH 3 2 C 4
1 only D 5
D
C C 2H35CO
CH CO22H
H 2 only
36 Which statements about the alcohol CH3CH2CH2OH are correct?
D C2H5CO2H 2 only
1 When CH CH2 of2 ethanoic acid? it forms propanoic acid.
CH
37 What is the empirical formula
3 OH is oxidised,
15 2019 SUM P12 Q37
37 What
A CH is 2the
O CH3CHB 2CH
2 empirical OH4O
formula
2CH burns in theCacid?
of ethanoic air to
C2form
H3O carbon dioxide
D C2andH4Owater.
2
3 CH3CH2CH2OH can be formed by the addition reaction between ethene and steam.
A CH2O B CH4O C C2H3O D C2H4O2
38 Which structure
A 1 and 2 onlyrepresents
B 1 andpropyl methanoate?
3 only C 2 and 3 only D 1, 2 and 3
38 2019
16 WhichWIN
structure
P11represents
Q37 A propyl methanoate? B
37 Propanoic acid reacts with calcium carbonate. The products of this reaction are
O A H dioxide
H H and water. H H BH O
calcium propanoate, carbon
O O C
H equation
C H C H C H H H H
C H
C H
C O C O
What is the for this reaction?
H O C C C C
H 2H5H H C C C O C H
A 2019
© UCLES 2C2H5COOH + Ca2H
CO3 H 2C COOCa + CO2 +HH2OH
5070/11/M/J/19 H
H H
C H
C O O
C H
C H H H
C O O
C H
C H
C H
H C
H C
H O C C
H H H C
H O C C
H C
H H
H H H H H H
Answers
1
alt
B
2 B
3 B
4 D
5 D
6 D
7 B
8 D
9 C
10 C
11 C
12 C
13 A
14 C
15 A
16 B
Organic Chemistry WS
alt
1 5070/21/M/J/16 A3 6
(a) Give one other use for esters such as propyl ethanoate.
.............................................................................................................................................. [1]
(b) Draw the structure of propyl ethanoate, showing all of the atoms and all of the bonds.
[1]
(c) A bottle of propyl ethanoate is opened in a room. Some of the propyl ethanoate evaporates
and then diffuses into the room.
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [1]
(ii) What happens to the rate of diffusion of propyl ethanoate as the temperature of the room
increases?
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [2]
alt
Cycloalkanes react in a similar way to alkanes.
H H
H H
C
H C C H
H C C H
C
H H
H H
cyclohexane
...........................................................................................................................................
...................................................................................................................................... [1]
...........................................................................................................................................
...................................................................................................................................... [1]
.............................................................................................................................................. [1]
.............................................................................................................................................. [2]
alt
C6H14 C6H12 + H2
Calculate the mass of cyclohexane that can be made from 258 g of hexane.
[Mr of cyclohexane = 84]
C, 85.7%; H, 14.3%
(i) Use the percentage composition by mass to show that the empirical formula of the
cycloalkane is CH2.
[2]
(ii) Draw the structure of the cycloalkane with an Mr of 56, showing all of the atoms and all of
the bonds.
[1]
[Total:10]
alt
(a) Draw the structure of ethyl methanoate, showing all of the atoms and all of the bonds.
[1]
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [1]
Explain, in terms of the kinetic particle theory, why this results in a decrease in the rate of
evaporation.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [2]
alt
Cycloalkenes react in a similar way to alkenes.
H H
H H
C
H C C
H C C
C
H H
H H
cyclohexene
...........................................................................................................................................
...................................................................................................................................... [1]
...........................................................................................................................................
...................................................................................................................................... [1]
.............................................................................................................................................. [1]
...................................................................................................................................... [1]
...................................................................................................................................... [1]
alt
C6H14 C6H10 + 2H2
Calculate the mass of cyclohexene that can be made from 258 g of hexane.
[Mr of cyclohexene = 82]
C, 88.2%; H, 11.8%
(i) Use the percentage composition by mass to show that the empirical formula of this
cycloalkene is C5H8.
[2]
Draw the structure of the cycloalkene, showing all of the atoms and all of the bonds.
[1]
[Total: 10]
alt
(a) Deduce the molecular formula of the alcohol having eight carbon atoms.
...............................................................................................................................................[1]
(i) Describe how the boiling point changes with the number of carbon atoms in the alcohol.
.......................................................................................................................................[1]
.......................................................................................................................................[1]
(iii) What is the physical state of pentanol at room temperature and pressure? Explain your
answer.
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[1]
...................................................................................................................................................
...............................................................................................................................................[2]
...............................................................................................................................................[2]
(i) Suggest the oxidising agent and describe the conditions used for this reaction.
...........................................................................................................................................
.......................................................................................................................................[2]
© UCLES 2016 5070/21/O/N/16
alt
10
Section B
Answer three questions from this section in the spaces provided. [1]
The total mark for this section is 30. [Total: 11]
6 5070/21/O/N/16 B7
B7 Ethenyl ethanoate, CH3CO2CH=CH2, is manufactured by passing a mixture of ethanoic acid,
ethene and oxygen over a catalyst at 200 °C.
(a) Draw an energy profile diagram for this reaction on the axes shown.
energy
reaction pathway
[3]
test ............................................................................................................................................
observation ...............................................................................................................................
[2]
© UCLES 2016 5070/21/O/N/16 [Turn over
alt
C2H4(g) + H2O(g) C2H5OH(g)
...................................................................................................................................................
13
...............................................................................................................................................[2]
(d) The
(b) Ethanol reacts
graph showswith methanoic
the acid,
percentage HCO
yield H, to form
of 2ethanol ethyl methanoate
at different and water.
temperatures.
Construct the equation for this reaction.
50
...............................................................................................................................................[1]
40
[Total: 10]
% yield 30
of ethanol
20
10
100 200 300 400
temperature / °C
(i) Describe how, and explain why, the percentage yield changes with temperature.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[3]
(ii) Suggest why the reaction is carried out at 300 °C and not at 200 °C.
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[2]
(c) Describe how, and explain why, the position of equilibrium changes when the pressure is
increased.
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[2]
alt
(a) State two properties of a homologous series.
...................................................................................................................................................
...............................................................................................................................................[2]
(b) Draw the structures of the branched and unbranched alkanes having four carbon atoms.
5 [2]
(c) The graph shows how the melting points of the first nine unbranched alkanes vary with the
number of carbon atoms per molecule.
–50
melting point
/ °C –100
–150
–200
1 2 3 4 5 6 7 8 9 10
number of carbon atoms per molecule
(i) Describe how the melting points of these alkanes change with the number of carbon
atoms.
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[2]
(ii) Use the graph to estimate the melting point of the unbranched alkane which has ten
carbon atoms.
......................................................°C [1]
© UCLES 2016 5070/22/O/N/16
(d) (i) Construct the equation for the complete combustion of pentane, C5H12.
Organic Chemistry WS Abul Fazal
.......................................................................................................................................[2]
.......................................................................................................................................[2]
(ii) Use the graph to estimate the melting point of the unbranched alkane which has ten
carbon atoms. 53
......................................................°C [1]
8 5070/22/O/N/16 A3
(d) (i) Construct the equation for the complete combustion of pentane, C5H12.
alt
.......................................................................................................................................[2]
(ii) Name the products of the incomplete combustion of pentane and explain why the
incomplete combustion of hydrocarbons is hazardous to health.
...........................................................................................................................................
.......................................................................................................................................[2]
[Total: 11]
8
9 5070/21/M/J/17 A5
A5 Ethanol and butanol are both alcohols.
alt
H H H H H H
H C C O H H C C C C O H
H H H H H H
ethanol butanol
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[2]
.......................................................................................................................................[1]
.......................................................................................................................................[2]
...............................................................................................................................................[1]
[1]
9
9 5070/21/M/J/17 A5
(e) Butanol can be converted into an alkene by loss of a molecule of water.
alt
Draw the structure of the alkene formed.
[1]
.......................................................................................................................................[1]
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[1]
[Total: 10]
alt
name structure boiling point / °C
methanoic acid HCO2H 101
ethanoic acid CH3CO2H 118
propanoic acid CH3CH2CO2H 141
butanoic acid CH3CH2CH2CO2H 164
pentanoic acid CH3CH2CH2CH2CO2H 186
(i) Deduce the general formula for the homologous series of unbranched carboxylic acids.
.......................................................................................................................................[1]
1. .......................................................................................................................................
...........................................................................................................................................
2. .......................................................................................................................................
...........................................................................................................................................
19 [2]
(c) Butanoic acid reacts with ethanol to make an ester.
(b) An aqueous solution of propanoic acid is a weak acid.
Name and draw the structure of this ester. Show all of the atoms and all of the bonds within
(i) What is the meaning of the term ?
the ester linkage.
...........................................................................................................................................
name .........................................................................................................................................
.......................................................................................................................................[1]
structure
(ii) Aqueous propanoic acid reacts with magnesium carbonate.
.......................................................................................................................................[1]
[2]
(d) Ethanoic acid is a liquid at room temperature and has a boiling point of 118 °C.
Describe the changes in both the arrangement and movement of the molecules when
ethanoic acid is heated from room temperature to 120 °C.
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
© UCLES 2017 5070/21/M/J/17
...................................................................................................................................................
Organic Chemistry WS Abul Fazal
...................................................................................................................................................
57
16
11 5070/22/M/J/17 B10
B10 The table shows some information about the homologous series of unbranched alcohols.
alt
name structure boiling point / °C
methanol CH3OH 65
ethanol CH3CH2OH 79
propanol CH3CH2CH2OH 97
(a) One of the characteristics of a homologous series is that it has a general formula.
(i) What is the general formula for the homologous series of unbranched alcohols?
.......................................................................................................................................[1]
(ii) Predict the boiling point of hexanol, an alcohol with six carbon atoms per molecule.
................................. °C [1]
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
17
...............................................................................................................................................[3]
(c) Butanol reacts with ethanoic acid to make an ester.
Show all of the atoms and all of the bonds within the ester linkage.
name ..................................................................................
structure
[2]
alt
H H
O O
C C C C
H O O H
O H
Name the homologous series of compounds which contain the –OH group.
...............................................................................................................................................[1]
H7C3OOC–CH(OH)–CH2–COOC3H7
What reagent and conditions are needed to make this diester from malic acid?
reagent .....................................................................................................................................
conditions .................................................................................................................................
[2]
How can aqueous malic acid and aqueous fumaric acid be distinguished when aqueous
bromine is added to a sample of each?
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[2]
alt
carboxylic acid formula melting point boiling point density in the
/ °C / °C liquid state
in g / cm3
methanoic acid HCOOH 100.7 1.22
ethanoic acid CH3COOH 118.0 1.05
propanoic acid C2H5COOH 141.1
butanoic acid C3H7COOH 165.6 0.96
(i) How does the boiling point change as the number of carbon atoms in the formula of the
carboxylic acids increases?
.......................................................................................................................................[1]
(iii) What is the physical state of ethanoic acid at 15.0 °C? Explain your answer.
...........................................................................................................................................
.......................................................................................................................................[1]
(iv) Why is it difficult to predict the melting point of pentanoic acid, C4H9COOH, using only
the information from the table?
.......................................................................................................................................[1]
(v) Draw the structure of propanoic acid showing all of the atoms and all of the bonds.
[1]
[Total: 10]
alt
H 2C
CH2 CH3CH = CH2
H 2C
cyclopropane
Complete the diagram to show the missing name, formula and conditions.
concentration
of propene propene
in mol / dm3 CH3CH = CH2
10
conditions
A5 Dilute ethanoic acid reacts with 0 carbonate.
sodium 1. ......................................
+ steam 0 + H2 / min
time
2. ......................................
Sodium ethanoate, CH3COONa, and two other compounds are formed.
Describe how the rate of this reaction changes with time. Explain your answer by referring to
(a) Construct
the name the equation for this reaction.
graph.......................................
propane
formula ................................... CH 3CH2CH3
...............................................................................................................................................[2]
...................................................................................................................................................
(b) The reaction of dilute ethanoic acid with sodium carbonate is endothermic.
...............................................................................................................................................[2]
[3]
(c) Explain
Describeinand terms of bond
explain themaking
effect ofand bond
increasing10breaking why this reaction
the concentration is endothermic.
of cyclopropane on the rate of
15 5070/22/O/N/17
this reaction. A5 [Total: 10]
A5 Dilute...................................................................................................................................................
ethanoic acid reacts with sodium carbonate.
...................................................................................................................................................
Sodium...................................................................................................................................................
ethanoate, CH3COONa, and two other compounds are formed.
...................................................................................................................................................
...................................................................................................................................................
(a) Construct the equation for this reaction.
...............................................................................................................................................[2]
...............................................................................................................................................[2]
...............................................................................................................................................[2]
(d) Describe and explain the effect of decreasing the temperature on the rate of this reaction.
(c) Ethanoic
(b) The reaction acidofreacts
dilutewith alcohols
ethanoic acidtowithform esters.carbonate is endothermic.
sodium
...................................................................................................................................................
Give
Explain oneinuseterms of esters.
of bond making and bond breaking why this reaction is endothermic.
...................................................................................................................................................
...............................................................................................................................................[1]
...................................................................................................................................................
...............................................................................................................................................[2]
[Total: 5]
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[2]
© UCLES 2017 5070/21/O/N/17
(c) Ethanoic acid reacts with alcohols to form esters.
Organic Chemistry
Give oneWS
use of esters. Abul Fazal
...............................................................................................................................................[1]
.......................................................................................................................................[1]
(ii) Construct the equation for the dissociation of hydrogen iodide molecules into ions.
61
.......................................................................................................................................[1]
16 5070/22/O/N/17 B6
(c) Hydrogen iodide reacts with ethene to form iodoethane.
alt
CH2 = CH2 + HI CH3 CH2I
13
...............................................................................................................................................[1]
(i) How does the boiling point change as the number of carbon atoms in the formula of the
alkenes increases?
.......................................................................................................................................[1]
(ii) What is the physical state of butene at –7 °C? Explain your answer.
...........................................................................................................................................
.......................................................................................................................................[1]
(iii) Why is it difficult to predict the melting point of propene using only the information from
the table?
.......................................................................................................................................[1]
[Total: 10]
alt
H H H O H
H C C O H H C C
H H H O
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[3]
...............................................................................................................................................[1]
(c) A sample of ethanol is heated with ethanoic acid in the presence of concentrated sulfuric acid
catalyst.
[1]
alt
H H H
H C C C H
H H
H C H
methylpropane
(a) Methylpropane reacts with chlorine in the presence of ultraviolet light to give several
compounds.
Suggest a structure for this compound. Show all of the atoms and all of the bonds.
[2]
alt
Write the molecular formula for this compound.
.......................................................................................................................................[1]
H
H H H
C H
C C C
C H
H CH3 H
H
propene cyclopropane
...........................................................................................................................................
.......................................................................................................................................[1]
...........................................................................................................................................
.......................................................................................................................................[1]
...........................................................................................................................................
.......................................................................................................................................[1]
(iv) Describe a chemical test to distinguish between unsaturated and saturated hydrocarbons.
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[2]
[Total: 10]
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.
To avoid the issue of disclosure of answer-related information to candidates, all copyright acknowledgements are reproduced online in the Cambridge International
Examinations Copyright Acknowledgements Booklet. This is produced for each series of examinations and is freely available to download at www.cie.org.uk after
the live examination series.
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.
alt
(a) Explain how naphtha is obtained from petroleum (crude oil).
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...............................................................................................................................................[3]
(b) One compound in the naphtha fraction has the formula C12H26.
(i) From this formula, how can you deduce that this compound is an alkane?
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[1]
(ii) The alkane, C12H26, can be cracked to form an alkene that has six carbon atoms per
molecule.
.......................................................................................................................................[2]
[2]
alt
(i) One molecule of ethene reacts with one molecule of chlorine.
Draw the structure of the product of this reaction. Show all of the atoms and all of the
bonds.
[1]
(ii) One molecule of ethane can react with two molecules of chlorine.
.......................................................................................................................................[1]
[Total: 10]
alt
H O H H H H
H C C O C C C C H
H H H H H
...............................................................................................................................................[1]
(b) Ester A reacts with hot aqueous sodium hydroxide to give two compounds, B and C.
[2]
(ii) Compound C has a relative molecular mass of 74 and is oxidised by warm acidified
potassium manganate(VII) to give butanoic acid.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[2]
alt
...........................................................................................................................................
.......................................................................................................................................[1]
[1]
...................................................................................................................................................
...............................................................................................................................................[1]
(i) Explain why the rate of diffusion of the ester decreases as the temperature decreases.
...........................................................................................................................................
...........................................................................................................................................
.......................................................................................................................................[1]
.......................................................................................................................................[1]
[Total: 10]
alt
The structures of these acids are shown.
H
H O H H
O O O O
C C C C C C C C
H O O H H O O H
O H H H
H
tartaric acid succinic acid
(a) Name the group which is present in tartaric acid but not in succinic acid.
...............................................................................................................................................[1]
(b) Tartaric acid is reduced to succinic acid by acidified aqueous potassium iodide.
What colour change would you observe in the reaction mixture when this reaction is carried
out?
...................................................................................................................................................
...............................................................................................................................................[1]
Calculate the minimum volume of 0.0200 mol / dm3 sodium hydroxide required to neutralise
25.0 cm3 of 0.0500 mol / dm3 succinic acid.
[Total: 7]
© UCLES 2018 5070/21/O/N/18 [Turn over
alt
(a) (i) Write the general formula for the alkane homologous series.
.......................................................................................................................................[1]
(ii) Each member of a particular homologous series has the same general formula.
.......................................................................................................................................[1]
...............................................................................................................................................[1]
(c) Construct the equation for the complete combustion of pentane, C5H12.
...............................................................................................................................................[2]
(d) Draw the structure of a branched alkane with the formula C5H12. Show all of the atoms and all
of the bonds.
[1]
.......................................................................................................................................[1]
(ii) What essential condition is needed for chlorine to react with pentane?
.......................................................................................................................................[1]
(f) 7 71
A hydrocarbon contains 90% carbon by mass.
23 (f) A(i)hydrocarbon
Deduce thecontains
empirical formula
90% of by
carbon thismass.
hydrocarbon.
alt
empirical formula ...........................................................[2]
[Total: 11]
5
24 5070/22/O/N/18 Q3
3 The structure of fumaric acid is shown.
alt
O
C H
H O C C O
H C
O
H
(a) How does this structure show that fumaric acid is an unsaturated compound?
...............................................................................................................................................[1]
What colour change would you observe in the reaction mixture when excess aqueous
fumaric acid is added to acidified aqueous potassium manganate(VII)?
.......................................................................................................................................[1]
(ii) Calculate the volume of 0.0500 mol / dm3 sodium hydroxide required to neutralise
20.0 cm3 of 0.0200 mol / dm3 fumaric acid.
[Total: 7]
6
25 5070/22/O/N/18 Q4
4 The alkenes are a homologous series of unsaturated hydrocarbons.
alt
(a) Describe two characteristics of a homologous series.
1. ...............................................................................................................................................
2. ...............................................................................................................................................
[2]
(b) Construct the equation for the complete combustion of butene, C4H8.
...............................................................................................................................................[2]
(c) Draw the structure of a branched alkene with the formula C4H8. Show all of the atoms and all
of the bonds.
[1]
.......................................................................................................................................[1]
.......................................................................................................................................[1]
7
.......................................................................................................................................[1]
[2]
© UCLES 2018 5070/22/O/N/18
(ii) What other piece of information is needed to deduce the molecular formula of this
Abul Fazal hydrocarbon? Organic Chemistry WS 2
.......................................................................................................................................[1]
74
16
26 5070/21/M/J/19 Q10
10 Cyclobutane and butene are both hydrocarbons.
alt
H H H H
H
H C C H H C C H
H C C H C C
H
H H H H
cyclobutane butene
...................................................................................................................................................
............................................................................................................................................. [1]
...................................................................................................................................................
...................................................................................................................................................
............................................................................................................................................. [1]
test ............................................................................................................................................
alt
H H H O
step 1 step 2
C C compound X H C C
H H H OH
..................................................................................................................................... [1]
..................................................................................................................................... [1]
..................................................................................................................................... [1]
[Total: 10]
alt
H H
H H H O
H C C OH
H C C C C
H C C H
OH
H H H
H H
cyclobutanol butanoic acid
...................................................................................................................................................
............................................................................................................................................. [1]
...................................................................................................................................................
............................................................................................................................................. [1]
(c) Describe a chemical test that can distinguish cyclobutanol from butanoic acid.
test ............................................................................................................................................
(d) Ethanol
(e) Calculatecan
thebe
percentage
converted by mass
into of carbon
methyl in cyclobutanol.
ethanoate in a two-step process.
H H H O
step 1 step 2
H
H C C OH compound X H C C
O C H
H H H
H
..................................................................................................................................... [1]
..................................................................................................................................... [1]
............................................................................................................................................. [1]
28 5070/21/O/N/19 Q6
(f) Ethanoic acid reacts with butanol, C4H9OH, to produce an ester.
alt
(i) Name the ester formed when ethanoic acid reacts with butanol.
..................................................................................................................................... [1]
[1]
[Total: 10]
..................................................................................................................................... [1]
78
[Total: 10]
29 5070/22/O/N/19 Q3
3 Petroleum (crude oil) is a mixture of hydrocarbons.
alt
(a) Describe and explain how petroleum is separated into different hydrocarbon fractions.
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
...................................................................................................................................................
5
............................................................................................................................................. [3]
kerosene ...................................................................................................................................
© UCLES 2019
naphtha .....................................................................................................................................
5070/22/O/N/19
[2]
(c) The refinery gas fraction contains methane, ethane and propane.
..................................................................................................................................... [1]
(ii) Give the general formula for the homologous series which contains methane, ethane
and propane.
..................................................................................................................................... [1]
30 5070/22/O/N/19 Q6
6 Butanoic acid, C3H7COOH, is a carboxylic acid.
alt
(a) Draw the structure of butanoic acid to show all of the atoms and all of the bonds.
[1]
(b) Describe the movement and arrangement of the particles in liquid butanoic acid.
movement .................................................................................................................................
arrangement .............................................................................................................................
[2]
(c)
explanation: ..............................................................................................................................
...................................................................................................................................................
[1]
6
31 5070/21/M/J/20 Q4
4 The table shows some properties of five esters.
alt
relative melting boiling
name structure molecular point point
mass / °C / °C
methyl ethanoate CH3COOCH3 74 –98 57
ethyl ethanoate CH3COOCH2CH3 88 –84 77
propyl ethanoate CH3COOCH2CH2CH3 102 –95 102
butyl ethanoate CH3COOCH2CH2CH2CH3 116 –78 126
pentyl ethanoate CH3COOCH2CH2CH2CH2CH3 130 –71 148
1. ...............................................................................................................................................
...................................................................................................................................................
2. ...............................................................................................................................................
...................................................................................................................................................
[2]
Explain why it is more difficult to predict the melting point than the boiling point of
hexyl ethanoate.
...................................................................................................................................................
...................................................................................................................................................
............................................................................................................................................. [1]
...................................................................................................................................................
............................................................................................................................................. [1]
............................................................................................................................................. [1]
10
32 5070/21/M/J/20 Q6
6 The structures of two carboxylic acids are shown.
alt
H O H H H O
H C C O H H C C C C O H
H H H H
..................................................................................................................................... [1]
...........................................................................................................................................
...........................................................................................................................................
..................................................................................................................................... [1]
...................................................................................................................................................
...................................................................................................................................................
............................................................................................................................................. [2]
(i) Give the formula of the calcium salt formed in this reaction.
..................................................................................................................................... [1]
[Total: 6]
16
33 5070/21/M/J/20 Q10
10 Fractional distillation and cracking are important processes in the conversion of petroleum (crude
oil) into useful substances.
alt
(a) Complete the sentence about petroleum (crude oil).
(b) Fractional distillation separates petroleum (crude oil) into fractions such as paraffin (kerosene)
and naphtha.
............................................................................................................................................. [1]
The flow chart shows some compounds that can be made from C10H22.
cracking
C10H22 C 3H 8 + C3H6 + C 4H 8
Explain why, in terms of their general formulae, C3H8 is an alkane and C3H6 is an alkene.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
..................................................................................................................................... [2]
alt
relative
relative melting point boiling point
name structure molecular melting point boiling point
name structure molecular / °C/ °C / °C/ °C
mass
mass
methyl methanoate
methyl methanoate HCOOCH
HCOOCH
3 3 60 60 32 32
methyl ethanoate
methyl ethanoate 3COOCH
CHCH 74 74 57 57
3COOCH
3 3
methyl propanoate
methyl propanoate 3CH
CHCH 2COOCH 88 88 80 80
3CH 2COOCH
3 3
methyl butanoate
methyl butanoate 3CH
CHCH 2CH 2COOCH 102102 102102
3CH 2CH 2COOCH
3 3
methyl pentanoate
methyl pentanoate 3CH
CHCH 2CH 2CH 2COOCH
3CH 2CH 2CH 2COOCH
3 3
(a)(a)These esters
These areare
esters part of aofhomologous
part series.
a homologous series.
(ii)(ii)Predict thethe
Predict boiling point
boiling of methyl
point pentanoate
of methyl pentanoate
..................................................... °C °C
..................................................... [1] [1]
(iii)(iii)Explain why
Explain it isit not
why possible
is not to predict
possible thethe
to predict melting point
melting of methyl
point pentanoate.
of methyl pentanoate.
...........................................................................................................................................
...........................................................................................................................................
(b)(b)At At
35 35
°C °C
methyl methanoate
methyl is aisgas.
methanoate a gas.
Explain how
Explain thethe
how data in the
data table
in the shows
table this.
shows this.
...................................................................................................................................................
...................................................................................................................................................
(c)(c)Methyl pentanoate
Methyl is used
pentanoate to flavour
is used food.
to flavour food.
Suggest oneone
Suggest other useuse
other forfor
esters.
esters.
© UCLES 2020
© UCLES 2020 5070/22/M/J/20
5070/22/M/J/20
alt
H H H H H H
H C C O H H C C C C O H
H H H H H H
ethanol alcohol B
............................................................................................................................................. [1]
[1]
............................................................................................................................................. [1]
...................................................................................................................................................
11
............................................................................................................................................. [1]
alt
(a) Fractional distillation separates petroleum (crude oil) into fractions such as bitumen and
naphtha.
(i) Which physical property allows the petroleum (crude oil) to be separated into fractions?
..................................................................................................................................... [1]
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
..................................................................................................................................... [2]
..................................................................................................................................... [1]
Use the general formula for an alkane to show that C10H22 is an alkane.
...................................................................................................................................................
...................................................................................................................................................
............................................................................................................................................. [2]
alt
density boiling point
alcohol formula
in g / cm3 in °C
methanol CH3OH 0.791 65
ethanol C2H5OH 0.789 79
propanol C3H7OH 0.803 97
butanol C4H9OH 0.810 117
pentanol C5H11OH 0.814 138
(i) What is the general trend in the density of the alcohols as the number of carbon atoms in
a molecule increases?
...........................................................................................................................................
..................................................................................................................................... [1]
(ii) Describe and explain the change in the boiling point of the alcohols as the number of
carbon atoms in a molecule increases.
...........................................................................................................................................
..................................................................................................................................... [1]
(b) Ethanol, C2H5OH, reacts with butanoic acid, C3H7CO2H, to produce an ester.
(i) What does the term strong mean, when applied to acids?
...........................................................................................................................................
..................................................................................................................................... [1]
alt
name .................................................................................................................................
structure
[2]
reagent .....................................................................................................................................
conditions .................................................................................................................................
[2]
..................................................................................................................................... [1]
(ii) State and explain how the rate of this reaction changes when the experiment is repeated
using dilute ethanoic acid.
...........................................................................................................................................
...........................................................................................................................................
..................................................................................................................................... [2]
[Total: 10]
...........................................................................................................................................
88
..................................................................................................................................... [2]
37 5070/22/O/N/20 Q6
(c) Methanoic acid reacts with propanol, C3H7OH, to form an ester.
alt
Name and draw the structure of this ester, showing all of the atoms and all of the bonds.
name .........................................................................................................................................
structure
10 [2]
(d) Ethanoic acid is present in vinegar.
(i) Name the organic compound which is converted to ethanoic acid when vinegar is made.
..................................................................................................................................... [1]
(ii) Describe and explain the change in the boiling point as the number of carbon atoms in a
molecule increases.
...........................................................................................................................................
..................................................................................................................................... [1]
[Total: 10]
Group
I II III IV V VI VII VIII
1 2
H He
hydrogen helium
Abul Fazal
Key 1 4
3 4 atomic number 5 6 7 8 9 10
Li Be atomic symbol B C N O F Ne
lithium beryllium name boron carbon nitrogen oxygen fluorine neon
7 9 relative atomic mass 11 12 14 16 19 20
11 12 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
sodium magnesium aluminium silicon phosphorus sulfur chlorine argon
23 24 27 28 31 32 35.5 40
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
potassium calcium scandium titanium vanadium chromium manganese iron cobalt nickel copper zinc gallium germanium arsenic selenium bromine krypton
39 40 45 48 51 52 55 56 59 59 64 65 70 73 75 79 80 84
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
rubidium strontium yttrium zirconium niobium molybdenum technetium ruthenium rhodium palladium silver cadmium indium tin antimony tellurium iodine xenon
85 88 89 91 93 96 – 101 103 106 108 112 115 119 122 128 127 131
89
55 56 57–71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
lanthanoids
Cs Ba Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
caesium barium hafnium tantalum tungsten rhenium osmium iridium platinum gold mercury thallium lead bismuth polonium astatine radon
57 58 59 60 61 62 63 64 65 66 67 68 69 70 71
lanthanoids La Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
lanthanum cerium praseodymium neodymium promethium samarium europium gadolinium terbium dysprosium holmium erbium thulium ytterbium lutetium
139 140 141 144 – 150 152 157 159 163 165 167 169 173 175
89 90 91 92 93 94 95 96 97 98 99 100 101 102 103
actinoids Ac Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
actinium thorium protactinium uranium neptunium plutonium americium curium berkelium californium einsteinium fermium mendelevium nobelium lawrencium
– 232 231 238 – – – – – – – – – – –
alt
The volume of one mole of any gas is 24 dm3 at room temperature and pressure (r.t.p.)
Data Booklet