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Organic Workbook

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OL Chemistry
Organic Workbook 2021

Abul Fazal
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Contents
Intro to Organic WS 5

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Alkanes WS 9
Alkenes WS 20
Alcohols WS 29
Carboxylic Acids WS 37
Organic Chemistry WS 43
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3

Homework

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Date Particulars
4

Homework

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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

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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

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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

B They3 have3 different


They burnrelative molecular
in air to masses.
form carbon dioxide and water.
34 How many of They
the molecules
burn in shown
air to form belong
carbontodioxide
the homologous
and water.series of alkanes?
C AThey
1, 2have
and only
3 carbon
B 1and andhydrogen
2 only in C their molecules.
1 and 3 only D 2 and 3 only
A 1, 2 and 3 C2H1
B
4
and 2 C
3H8
only C C1Hand 3 only
4 10 C5H10D 2 C 6H14
and 3 only
D They have the same molecular formula.
A 1 B 2 C 3 D 4
8 2018
39 WIN P11
How many of theQ35
structures show an unsaturated hydrocarbon molecule?
35 The diagram shows the structural formula of an organic compound.
O

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

Which statement about this compound is correct?

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.

© UCLES 2018 5070/11/O/N/18

Intro to Organic WS Abul Fazal


7

12
9 2019 WIN P11 Q32
32 Which statements are true for homologous series?

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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

33 Alkanes are saturated compounds containing carbon and hydrogen only.

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

Which pair of structures are isomers?

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

© UCLES 2019 5070/11/O/N/19

Abul Fazal Intro to Organic WS


8

Answers
1

alt
A

2 D

3 A

4 C

5 B

6 A

7 D

8 A

9 D

Intro to Organic WS Abul Fazal


11

34 Which compound, on combustion, never forms carbon?


9
A carbon monoxide
B ethanol Alkanes WS
C ethene

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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

© UCLES 2014 5070/11/M/J/14 [Turn over


C D

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

A 1, 2 and 3 B 1 and 4 C 2 and 4 D 3 only


4 2014 WIN P11 Q37
37 Which alkane, when any one hydrogen atom is substituted by a chlorine atom, will not produce

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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?

A C2H5 has the formula C2H4.


C2H51CO2Ethane H

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

35 When cracked, one mole


C2Hof a compound,2HX, →
5OH + CH3CO
produces
CH3CO2one
C2Hmole of propene and one mole of
5 + H2O
© UCLES 2014 5070/11/O/N/14
hydrogen.
What is the formula of the ester formed when methanol reacts with butanoic acid, C3H7CO2H?
X → C3H6 + H2
A C2H5CO2C2H5
What type of compound is X?
B C3H7CO2C2H5
A an alcohol
C CH3CO2C3H7
B an alkane
D C3H7CO2CH3
C an alkene
D a carboxylic acid

36 Which is a correct definition of isomers?

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

What type of compound is X?


14
9 2015
A anSUM P12 Q39
alcohol
39 Which statement about the properties of the four alkanes from methane to butane is not correct?
B an alkane
A
C an alkene members of the series differ in formula by CH2.
Successive
B
D They increase
a carboxylic in boiling point.
acid
C They increase in viscosity.
D They share the same empirical formula.

40 Which of these polymers is a protein?

A (C2H3Cl )n B (C5H8O2)n C (C6H10O5)n D (C2H3NO)n

© UCLES 2015 5070/12/M/J/15

© UCLES 2015 5070/12/M/J/15

Abul Fazal Alkanes WS


A clay particles
B microbes
C nitrates 12
D odours
10 2015 WIN P12 Q34
34 Which diagram shows the isomer of butane?

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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

Which statement is correct?

A All three molecules are unsaturated hydrocarbons.


B All three molecules have the same empirical formula.
C W has the lowest boiling point.
D X is an isomer of Y.

38 How many of the following statements about ethanol are correct?

1 molecular formula is C2H6O


2 manufactured from ethane and steam
3 oxidises to ethanoic acid
4 produced by the fermentation of glucose
5 used as a fuel
Alkanes WS Abul Fazal
6 used as a solvent

A 3 B 4 C 5 D 6
H Cl n

Which statement about this polymer is correct?


13
Cl H

A The monomer is C C. 13
12 2016 SUM P11 Q38
H
Clalkanes

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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.

D The polymer has a lower melting point than the monomer.


39 2016
13 Which SUM P12about
statement Q39ethanoic acid is correct?
39 How can the following reaction be described?
A Ethanoic acid can be made by the catalysed 2 addition of steam to ethene.
8H18 → acid
B Propanoic acid can react with Cethanoic C4H10 + 2C2H4an ester.
to produce
1 Gas X has the following properties.
CA Solutions
combustionof 1.0 mol / dm3 ethanoic acid and 1.0 mol / dm3 hydrochloric acid will react with
1 colourless
magnesium at equal rates.
B cracking
2 no of
D The formula effect on either
ethanoic acidred or blue
is CH 3CO2litmus
H. papers
C oxidation
3 no effect on limewater
D reduction
40 Polymer Z4hasflammable
the structure shown.
13
What is gas X? O O 14 O O
14 2016 WIN P11 Q39
34 The table shows some atmospheric pollutants and their possible effects.
A ammonia
39 Compound Q hasCthe formula C C4HN10. N C C N N
Which row is not correct?
B chlorine
Which H
H Q is correct?
statement about compound H H

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?

A They all contain more electrons than protons.


©38 Which
UCLES 2016statement about isomers of a compound is always correct?
5070/11/M/J/16
B They all contain more neutrons than protons.
A They have different empirical formulae.
C They all contain the same number of electrons.
Abul FazalB They have different relative molecular masses. Alkanes WS
D They all contain the same number of protons.
C They have only carbon and hydrogen in their molecules.
A B C D
H Cl CH3 H 14 CH3 H Cl CH3

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

D two compounds undergo an addition reaction with bromine?


Which

A W and Y B W and Z C X and Y D X and Z


33 2017
18 FossilSUM
fuels are
P11used
Q37to power some internal combustion engines.
37 One mole
Which of eachare
pollutants alkane undergoes
produced by an complete combustion.
internal combustion engine burning fossil fuels?
Which alkane will produce
1 carbon seven moles of products?
monoxide
A CH4 2 nitrogenBoxides
C2H6 C C3H8 D C4H10

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

36 The structure of compound X is shown.

CH3–CH2–CH2–CH2–OH

Which statement is not correct?

A X is an alcohol because it contains an –OH group.


B X is an isomer of propanol.
C X would burn in air to form carbon dioxide and water.
D X would have a higher boiling point than ethanol.

37 After
© UCLES which conversion does the product contain
2017 more carbon atoms than the reactant?
5070/11/M/J/17

A ethanol to ethanoic acid


B ethanol to ethyl ethanoate
Alkanes WS Abul Fazal
C ethene to ethane
D ethene to ethanol
13

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

Abul FazalD CCHCH2BrCH2CH2CH2Br


3CH2CH2CH2Br Alkanes WS
D CH3CH2CH2CH2Br
A metal
Which compounds
impurities can be removed by which treatment?
B nitrate fertilisers
filtration use of carbon chlorination
C oxygen 16
A harmful microbes solids unpleasant odours
D sulfuric acid and tastes
23 2018
B WIN P11 microbes
harmful Q34 unpleasant odours solids
and tastes
34 How many of the molecules shown belong to the homologous series of alkanes?

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

B Both occur naturally.


34 Which organic compound requires the least number of moles of oxygen for the complete
C Margarine
combustion has mole
of one the higher
of themelting point.
compound?
D Vegetable oil has fewer carbon-carbon double bonds than margarine.
A C3H7OH B C3H7COOH C C3H8 D C4H8

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

© UCLES 2018 5070/12/O/N/18 [Turn over

Alkanes WS Abul Fazal


A 1, 2, 3 and 4
B 1, 2, and 3 only
C 1 and 4 only 17
D 3 and 4 only
26 2019 WIN P11 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

Which pair of structures are isomers?

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

© UCLES 2019 5070/11/O/N/19

Abul Fazal Alkanes WS


18

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

Which pair of structures are isomers?

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

© UCLES 2019 5070/12/O/N/19

Alkanes WS Abul Fazal


19

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

Abul Fazal Alkanes WS 2


20

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

A CH3CH=CH2 CH3CH(OH)CH3 only


B CH3CH2CH=CH2 CH3CH2CH2CH2OH only
C CH3CH=CHCH3 CH3CH(OH)CH2CH3 only
D (CH3)2C=CH2 (CH3)2CHCH2OH only

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

D It removes C Cand odours.


H tastes C C H H C C C C 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.

A 1, 2 and 3 B 1 and 4 C 2 and 4 D 3 only

40 When ethanol reacts with ethanoic acid, the ester ethyl ethanoate is formed.

C2H5OH + CH3CO2H → CH3CO2C2H5 + H2O

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

B It has the formula C5H12O3.


C It is formed by an addition reaction. 21
34 How many of the structures show an unsaturated hydrocarbon molecule?
D It is propyl ethanoate.
H
4 2016 SUM P11 Q37
37 How can alkenes be manufactured? H C H

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?

1 They turn aqueous bromine from brown to colourless.


2 Their general formula is CnH2n.
3 They burn in air to form carbon dioxide and water.

A 1, 2 and 3 B 1 and 2 only C 1 and 3 only D 2 and 3 only

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

Abul Fazal Alkenes WS


D NO2 forms acid rain
36 The diagram shows the structures of two hydrocarbons, X and Y.

34 How many moles of ethanoic acid,HCH3CO2H,22 H of magnesium?


react with one mole

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.

Student 1 Hydrocarbon X is an13


isomer of Y.
8 2016 WIN P11 Q36
Student 2 Hydrocarbon X is unsaturated but Y is saturated.
36 The diagram shows the structures of two hydrocarbons, X and Y.
Which students are correct?
H H
A both 1 and 2
H H C H H C H H
B 1 only
H C C H C C
C 2 only
D neither 1 nor 2 H H C H H C H H

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

Alkenes WS Abul Fazal


38 An unsaturated hydrocarbon with six carbon atoms contains only three C=C double bonds. This
hydrocarbon is reacted with excess hydrogen at a high temperature.
A C6H14 B C8H18 C C10H22 D C12H26
A argon
36 How many moles of ethanoic acid, CH3CO2H,23
B hydrogen react with one mole of magnesium?

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

12 2017 SUM P11 Q36 O


36 Each
O C of compounds
O CHW, X,CH
Y and ZCH
is either
CHan unbranched
CH3 CH alkaneCH
or an unbranched
CH3 C alkene.
3 2 2 3 2

© UCLES 2016 W C9H18 5070/12/O/N/16 H over


O[Turn

A 1 X C9H20 B 2 C 3 D 4
Y C10H20
Z C10H22

Which two compounds undergo an addition reaction with bromine?


© UCLES 2016 5070/12/O/N/16 [Turn over
A W and Y B W and Z C X and Y D X and Z

37 One mole of each alkane undergoes complete combustion.

Which alkane will produce seven moles of products?

A CH4 B C2H6 C C3H8 D C4H10

38 Which statement about macromolecules is correct?

A Nylon and Terylene are both polyesters.


B Proteins and nylon have the same monomer units.
C Proteins have the same amide linkages as nylon.
D Terylene and fats are esters but with different linkages.

Abul Fazal Alkenes WS

© UCLES 2017 5070/11/M/J/17 [Turn over


12

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?

A Nylon andS Terylene are both


T polyesters.
B A Proteins and nylon have
ethane the same monomer units.
propane
C B Proteins have the same
ethene amide linkages as nylon.
propene
D C Terylene and fats are esters
propane ethanebut with different linkages.
D propene ethene

13
15 2017 WIN P11 Q36
36 Which row correctly describes alkenes?

result when shaken


general formula
with aqueous bromine

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

© UCLES 2017 5070/12/M/J/17


37 The table contains statements about processes by which ethanol is produced on a large scale
from
Alkenes WS ethene and from glucose. Abul Fazal

from ethene from glucose


D Dneutralisation
neutralisation

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

16 2018 SUM P11 Q37


37 37Z isZ aiscompound
a compound that:
that:

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

17 2018 SUM P12 Q37


33 A
37 Compound Q is alkene,
straight-chain a hydrocarbon that has no
C4H8, undergoes anisomers. Compound
addition reaction withQbromine.
does not decolourise bromine
in the dark.
What is the possible structure of the product?
Which compound could be Q?
A CH3CHBrCH2CH2Br
A C3H6 B C3H8 C C4H8 D C4H10
B CH3CHBrCHBrCH3

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

18 2019 SUM P11 Q35


35 When a molecule of a saturated hydrocarbon is cracked, it forms two molecules X and Y.

Which row is correct?

X Y

A H2 CnH2n
B H2 CnH2n+2
C H2O CnH2n
D H2O CnH2n+2

Abul Fazal Alkenes WS


A adding carbon
B – –
chlorination – –
+ + + + – – ––

C – –
desalination – – 26+ + + + –
+ + + + – + + + + –
D filtration– – – – – + + + + –
+ + + + – – – –
19 2019 SUM P12 Q33
33 A molecule of compound Q has three C–C single bonds and ten C–H bonds only. It has no other

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 empirical formula molecular formula general formula


B empirical formula general formula molecular formula
C general formula molecular formula empirical formula
D molecular formula empirical formula general formula

© UCLES 2019 5070/12/M/J/19


13 [Turn over
21 2019 WIN P11 Q34
34 When butene reacts with bromine, which compound could be made?

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

36 Which statements about the alcohol CH3CH2CH2OH are correct?

1 When CH3CH2CH2OH is oxidised, it forms propanoic acid.


2 CH3CH2CH2OH burns in the air to form carbon dioxide and water.
3 CH3CH2CH2OH can be formed by the addition reaction between ethene and steam.
Alkenes WS Abul Fazal
A 1 and 2 only B 1 and 3 only C 2 and 3 only D 1, 2 and 3
Z is removed from the exhaust gases in a catalytic converter by reduction.

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?

A It decolourises aqueous bromine.


B It has a sweet smell.
C It is a good solvent for organic compounds.
D It produces carbon dioxide when burned.

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.

36 Which term describes the structure of Terylene?


36 Which term describes the structure of Terylene?
A polyalkene
A 2019
© UCLES polyalkene 5070/12/O/N/19 [Turn over
B polyamide
B polyamide
C polyester
C polyester
D protein
D protein

37 Which process is involved in the formation of ethanol from ethene?


37 Which process is involved in the formation of ethanol from ethene?
A addition
A addition
B combustion
B combustion
Abul Fazal
C polymerisation Alkenes WS
C polymerisation
D substitution
D substitution
28

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

Alkenes WS 2 Abul Fazal


39 Fats, carbohydrates and proteins all contain which chemical elements?

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

Which compounds are alcohols?

A 1 only
B 1 and 2 only
C 1, 2 and 3
D 4

© UCLES 2014 5070/11/M/J/14

Abul Fazal Alcohols WS


A Ammonia is formed during the production of the polymer.
B Hydrolysis of the polymer produces X and Y.
C The polymer is a polyamide. 30
D The polymer is formed by a condensation reaction.
2 2014 SUM P12 Q38
38 The structural formulae of some organic compounds are shown below.

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

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


3 2015 SUM P11 Q34
34 Which statement is correct?

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

C Ethanol will decolourise acidified potassium manganate(VII).


O H

D The structure of ethyl ethanoate is H C O C H.

35 When cracked, one mole of a compound, X, produces one mole of propene and one mole of
hydrogen.

X → C3H6 + H2

What type of compound is X?

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?

1 molecular formula is C2H6O


2 manufactured from ethane and steam
3 oxidises to ethanoic acid
4 produced by the fermentation of glucose
© UCLES 2015 5 used as a fuel 5070/11/O/N/15

6 used as a solvent

A 3 B 4 C 5 D 6

39 Proteins and nylon both possess the same amide linkages.

Which arrangement of atoms represents an amide linkage?

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

© UCLES 2015 5070/12/O/N/15 [Turn over

Abul Fazal Alcohols WS


32

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

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

essential building blocks 12


13
8 2016
35 Amino SUMacids P12
are Q36 in the human body. Macromolecules in food are
hydrolysed to form amino acids.
34
36 One
Winemole
is anofalcoholic
each alkane
drinkundergoes complete
that contains combustion.
ethanol. If wine is left exposed to the air for too long, it
can become acidic.
Which macromolecules provide the body with amino acids?
Which alkane will produce seven moles of products?
AThiscarbohydrates
is because the ethanol is ......1...... to the acid ......2...... .
A CH4 B C2H6 C C3H8 D C4H10
BWhich
fatsword and formula correctly complete gaps 1 and 2?

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?

A CH3OH and CH3COOH


B CH3OH and C2H5COOH
Abul FazalC C2H5OH and CH3COOH Alcohols WS

D C2H5OH and C2H5COOH


13
34
34 When butene reacts with bromine, which compound 13 could be made?
12
13
34 2019
14 When SUM
buteneP11 Q36
reacts withAbromine, which compound could be made?B
36
34 The
Whenstructures and names
butene reacts of threewhich
with bromine, alcohols, P, Q and
compound R be
could aremade?
shown. The structures may not be

alt
named correctly. Br H A H H Br BrB H H

H P CBr C HAC H C H H H C Br BrCB HC RHC H


Q
H Br Br C
C H C H C H Br C Br H C H
H H H H HH H H C H HH C HH HH H
H C Br C H C H C H H H C H C H C H C H H
H C O H H C C O H H C C C O H
Br H H H H H H H
H C H H HD H H
Br H C Br H
propanol ethanol Br H D methanol
H Br

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

© UCLES 2019 5070/12/O/N/19 [Turn over


© UCLES 2019 5070/11/O/N/19 [Turn over
© UCLES
© UCLES 2019
2019 5070/11/O/N/19
5070/11/M/J/19 [Turn over

Alcohols WS Abul Fazal


35

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

39 Which two compounds react together to form CH3CH2COOCH3?

A ethanoic acid and ethanol


B methanoic acid and ethanol
C methanoic acid and propanol
D propanoic acid and methanol

40 Which compound might be suitable to flavour a soft drink?

A CH3CH2CH2COOCH3
B CH3CH2CH2CH2CH2OH
C CH3CH2CH2CH2COOH
D CH3CHCHCH2CH3

© UCLES 2019 5070/12/O/N/19

Abul Fazal Alcohols WS


36

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

Alcohols WS 2 Abul Fazal


D C protein
Terylene
32 What is not essential for photosynthesis?
D Terylene
37
A
36 Whichcarbon dioxide
statement about the properties of propane and hexane is correct?
B sugar statement about the properties of propane and hexane is correct?

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

What is the liquid?

A aqueous ammonia
B ethanoic acid
C ethyl ethanoate
D sodium hydroxide

© UCLES 2014 5070/12/M/J/14

Abul Fazal Carboxylic Acids WS


A Carbohydrates, proteins and fats are all natural macromolecules.
B Terylene contains the same linkages as a protein.
C 38 are formed.
When a carbohydrate is hydrolysed, sugars
D When a protein is hydrolysed, amino acids are formed.
4 2014 WIN P12 Q37

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

1 It would react with excess aqueous sodium hydroxide in a 1 : 1 molar ratio.


2 In aqueous solution, it would have a pH of 9.5.
3 It would react with an alcohol to form an ester.

A 1 only B 1 and 2 C 2 and 3 D 3 only

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

Which row is correct?

reacts with aqueous


name of acid sodium carbonate to
13
produce carbon dioxide

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 CH4 B C2H6 C C3H8 D C4H10


40 Which polymer contains only three different elements?
9 2017 SUM P12 Q35
A protein
35 Ethanoic acid is formed when ethanol is reacted with acidified potassium manganate(VII).
B poly(ethene)
What is the name of this process?
C poly(propene)
A combustion
D starch
B condensation
C oxidation
D polymerisation

36 The structure of compound X is shown. 14


10 2017 WIN P11 Q39
39 Which compound has a pH of lessCH
than 7 in2–CH
3–CH aqueous
2–CHsolution?
2–OH

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

37 After which conversion does


C the product contain more carbon D
atoms than the reactant?

A ethanol to ethanoic acidO H O


B ethanol to ethyl H C
ethanoate H C C H H
C ethene to ethane O H O C C H
H
D 2017
© UCLES ethene to ethanol 5070/11/M/J/17
H H

Abul Fazal Carboxylic Acids WS


40

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

Which alcohol is oxidised to form 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

39 Some properties of compound J are listed.


© UCLES 2017 5070/12/O/N/17
It reacts with potassium carbonate to produce carbon dioxide.
It reacts with ethanol to produce a sweet-smelling liquid.

Carboxylic Acids WS It reacts with sodium hydroxide to produce a salt. Abul Fazal

What is a possible identity of J?


propanol ethanol methanol
12
Which structures are correctly named? 41
35 Which reaction is an addition reaction? 12
A P, Q and R B P only C Q only D R only
13
35 Which reaction
A making is anand
ethane addition
ethenereaction?
from butane
13 2019 SUM P11 Q37
34 B
37 When
What isbutene reacts with
the empirical
making ethene bromine,
formula offromwhich
ethanoic compound
acid? could be made?
A ethane and hydrogen
ethene from butane
butane

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 3 H (CH2H5COO)2Ca + CO2 +HH2OH H H


B 2C2H5COOH + CaCO

C 2C3H7COOH + Ca2CCO3 2C3H7COOCa + CO2 + H2O D

D 2C3H7COOH C 3 O (CH3H7COO)2Ca + CO2 +H H2O


H +H CaCO D
O H 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

© UCLES 2019 5070/12/M/J/19

© UCLES 2019 5070/12/M/J/19


© UCLES 2019 5070/11/O/N/19 [Turn over

Abul Fazal Carboxylic Acids WS


42

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

Carboxylic Acids WS Abul Fazal


43

Organic Chemistry WS

alt
1 5070/21/M/J/16 A3 6

A3 Esters, such as propyl ethanoate, are often used as solvents.

(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.

(i) What is meant by the term diffusion?

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

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

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

(ii) What happens to the rate of diffusion of propyl ethanoate as the temperature of the room
increases?

Explain your answer in terms of the kinetic particle theory.

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

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

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

Abul Fazal Organic Chemistry WS 2

© UCLES 2016 5070/21/M/J/16


44
14
2 5070/21/M/J/16 B8
B8 Cyclohexane, C6H12, is a cycloalkane.

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

(a) Cyclohexane is a saturated hydrocarbon.

(i) What is the meaning of the term saturated?

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

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

(ii) What is the meaning of the term hydrocarbon?

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

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

(b) Construct the equation for the complete combustion of cyclohexane.

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

(c) Cyclohexane reacts with chlorine in the presence of ultraviolet light.

This is a substitution reaction.

Write the molecular formulae of two products of this reaction.

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

© UCLES 2016 5070/21/M/J/16

Organic Chemistry WS Abul Fazal


45
15
2 5070/21/M/J/16 B8
(d) Cyclohexane can be manufactured from hexane as shown in the equation.

alt
C6H14 C6H12 + H2

Calculate the mass of cyclohexane that can be made from 258 g of hexane.
[Mr of cyclohexane = 84]

mass of cyclohexane = ...................................................... g [2]

(e) Another cycloalkane has the following percentage composition by mass.

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]

© UCLES 2016 5070/21/M/J/16 [Turn over

Abul Fazal Organic Chemistry WS 2


46
6
3 5070/22/M/J/16 A3
A3 Esters are used as food flavourings and solvents.

alt
(a) Draw the structure of ethyl methanoate, showing all of the atoms and all of the bonds.

[1]

(b) Ethyl ethanoate evaporates at room temperature.

(i) What is meant by the term evaporation?

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

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

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

(ii) A sample of ethyl ethanoate in a beaker is moved into a colder room.

Explain, in terms of the kinetic particle theory, why this results in a decrease in the rate of
evaporation.

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

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

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

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

© UCLES 2016 5070/22/M/J/16

Organic Chemistry WS Abul Fazal


47
14
4 5070/22/M/J/16 B8
B8 Cyclohexene, C6H10, is a cycloalkene.

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

(a) Cyclohexene is an unsaturated hydrocarbon.

(i) What is meant by the term unsaturated?

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

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

(ii) What is meant by the term hydrocarbon?

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

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

(b) Construct the equation for the complete combustion of cyclohexene.

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

(c) Cyclohexene reacts with bromine.

This is an addition reaction.

(i) Write the molecular formula of the product of this reaction.

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

(ii) What would be observed in this reaction?

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

© UCLES 2016 5070/22/M/J/16

Abul Fazal Organic Chemistry WS 2


48
15
4 5070/22/M/J/16 B8
(d) Cyclohexene can be manufactured from hexane as shown in the equation.

alt
C6H14 C6H10 + 2H2

Calculate the mass of cyclohexene that can be made from 258 g of hexane.
[Mr of cyclohexene = 82]

mass of cyclohexene = ....................................................... g [2]

(e) Another cycloalkene has the following percentage composition by mass.

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]

(ii) The cycloalkene has a relative molecular mass, Mr, of 68.

Draw the structure of the cycloalkene, showing all of the atoms and all of the bonds.

[1]

[Total: 10]

© UCLES 2016 5070/22/M/J/16 [Turn over

Organic Chemistry WS Abul Fazal


49
4
5 5070/21/O/N/16 A3
A3 The alcohols are a homologous series with the general formula CnH2n+1OH.

alt
(a) Deduce the molecular formula of the alcohol having eight carbon atoms.

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

(b) The table shows some information about different alcohols.

alcohol formula melting point boiling point density


/ °C / °C in g / cm3
ethanol C2H5OH –117 79 0.789
propanol C3H7OH –126 98 0.804
butanol C4H9OH –89 117
pentanol C5H11OH –79 138 0.815
hexanol C6H13OH –47 158 0.820

(i) Describe how the boiling point changes with the number of carbon atoms in the alcohol.

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

(ii) Estimate the density, in g / cm3, of butanol.

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

(iii) What is the physical state of pentanol at room temperature and pressure? Explain your
answer.

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

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

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

(c) How does viscosity change in the homologous series of alcohols?

Explain your answer.

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

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

(d) Construct the equation for the complete combustion of propanol.

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

(e) Propanol can be oxidised to propanoic acid.

(i) Suggest the oxidising agent and describe the conditions used for this reaction.

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

.......................................................................................................................................[2]
© UCLES 2016 5070/21/O/N/16

Abul Fazal Organic Chemistry WS 2


50
5
5 5070/21/O/N/16 A3
(ii) Draw the structure of propanoic acid, showing all the atoms and all the bonds.

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.

CH3CO2H + CH2=CH2 + ½O2 CH3CO2CH=CH2 + H2O

The reaction is exothermic.

(a) Draw an energy profile diagram for this reaction on the axes shown.

On your diagram label


• the reactants and products,
• the enthalpy change for the reaction,
• the activation energy.

energy

reaction pathway

[3]

(b) Ethenyl ethanoate is an unsaturated compound.

Describe a chemical test for an unsaturated compound.

test ............................................................................................................................................

observation ...............................................................................................................................
[2]
© UCLES 2016 5070/21/O/N/16 [Turn over

Organic Chemistry WS Abul Fazal


51
12
7 5070/21/O/N/16 B8
B8 Ethanol can be manufactured by reacting ethene with steam in a closed reaction vessel.

alt
C2H4(g) + H2O(g) C2H5OH(g)

The reaction is exothermic.

(a) State two conditions for this reaction.

...................................................................................................................................................
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]

© UCLES 2016 5070/21/O/N/16

Abul Fazal Organic Chemistry WS 2


52
4
8 5070/22/O/N/16 A3
A3 The alkanes are a homologous series of hydrocarbons.

alt
(a) State two properties of a homologous series.

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

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

(b) Draw the structures of the branched and unbranched alkanes having four carbon atoms.

Show all the atoms and all the bonds.

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]

© UCLES 2016 5070/22/O/N/16 [Turn over

Abul Fazal Organic Chemistry WS 2


54

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

(a) Describe the manufacture of ethanol from ethene.

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

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

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

(b) Ethanol is used as a fuel and as a constituent of alcoholic beverages.

(i) State one other use of ethanol.

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

(ii) Construct an equation to show the incomplete combustion of ethanol.

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

(c) Ethanol can be oxidised to form ethanoic acid.

Name a reagent that can be used for this oxidation.

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

(d) Draw the structure of an alcohol that is an isomer of butanol.

Show all of the atoms and all of the bonds.

[1]

© UCLES 2017 5070/21/M/J/17

Organic Chemistry WS Abul Fazal


55

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.

Show all of the atoms and all of the bonds.

[1]

(f) Butene can be polymerised to give poly(butene).

(i) What type of polymerisation occurs?

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

(ii) Poly(butene) is non-biodegradable.

What does the term non-biodegradable mean?

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

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

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

[Total: 10]

© UCLES 2017 5070/21/M/J/17 [Turn over

Abul Fazal Organic Chemistry WS 2


56
18
10 5070/21/M/J/17 B10
B10 The table shows some information about the homologous series of unbranched carboxylic acids.

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

(a) A homologous series has a general formula.

(i) Deduce the general formula for the homologous series of unbranched carboxylic acids.

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

(ii) Describe two other properties of a homologous series.

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.

Construct the equation for this reaction.

.......................................................................................................................................[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

butanol CH3CH2CH2CH2OH 117

pentanol CH3CH2CH2CH2CH2OH 138

(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]

(b) Describe the manufacture of ethanol by the fermentation of aqueous glucose.

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

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

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

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

...................................................................................................................................................
17
...............................................................................................................................................[3]
(c) Butanol reacts with ethanoic acid to make an ester.

Name and draw the structure of this ester.

Show all of the atoms and all of the bonds within the ester linkage.

name ..................................................................................

structure

[2]

(d) Ethanol is a gas at 100 °C.


© UCLES 2017 5070/22/M/J/17
Describe the changes in the arrangement and movement of the molecules when ethanol is
cooled from 100 °C to 25 °C.
Abul Fazal Organic Chemistry WS 2
...................................................................................................................................................
58
8
12 5070/21/O/N/17 A4
A4 The structure of malic acid is shown.

alt
H H
O O
C C C C
H O O H
O H

(a) Malic acid is a carboxylic acid because it contains a –COOH group.

Malic acid also contains an –OH group.

Name the homologous series of compounds which contain the –OH group.

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

(b) A diester of malic acid has the formula shown.

H7C3OOC–CH(OH)–CH2–COOC3H7

What reagent and conditions are needed to make this diester from malic acid?

reagent .....................................................................................................................................

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

(c) When heated, malic acid forms fumaric acid.

HOOC–CH(OH)–CH2–COOH HOOC–CH=CH–COOH + H2O


malic acid fumaric acid

How can aqueous malic acid and aqueous fumaric acid be distinguished when aqueous
bromine is added to a sample of each?

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

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

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

© UCLES 2017 5070/21/O/N/17

Organic Chemistry WS Abul Fazal


59
13
13 5070/21/O/N/17 B6
(c) The table shows some properties of four carboxylic acids.

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]

(ii) Estimate the density, in g / cm3, of liquid propanoic acid.

density ............................................... g / cm3 [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]

© UCLES 2017 5070/21/O/N/17 [Turn over

Abul Fazal Organic Chemistry WS 2


60
18
14 5070/21/O/N/17 B9
B9 Cyclopropane is converted to propene when heated.

alt
H 2C
CH2 CH3CH = CH2
H 2C

cyclopropane

(a) Explain why cyclopropane and propene are isomers.


19
...............................................................................................................................................[1]
(e) Propene undergoes addition reactions. Two addition reactions of propene are shown in the
(b) The graph shows how the concentration of propene in this reaction changes with time.
diagram.

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

What is the name of this type of reaction?

13
...............................................................................................................................................[1]

(d) The table shows some properties of five alkenes.

alkene formula melting point boiling point


/ °C / °C
ethene C 2H4 –168.9 –103.6
propene C 3H6 –47.3
© UCLES 2017 5070/22/O/N/17
butene C 4H8 –185.2 –6.2
pentene C5H10 –165.0 30.0
hexene C6H12 –139.7 63.4

(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]

Abul Fazal Organic Chemistry WS 2


62
8
17 5070/21/M/J/18 Q4
4 This question is about ethanol and ethanoic acid.

alt
H H H O H

H C C O H H C C

H H H O

ethanol ethanoic acid

(a) Describe the manufacture of ethanol by fermentation.

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

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

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

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

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

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

(b) Ethanol can be oxidised by oxygen to form ethanoic acid.

Construct the equation for this reaction.

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

(c) A sample of ethanol is heated with ethanoic acid in the presence of concentrated sulfuric acid
catalyst.

Draw the structure of the product of this reaction.

Show all of the atoms and all of the bonds.

[1]

© UCLES 2018 5070/21/M/J/18

Organic Chemistry WS Abul Fazal


63
18
18 5070/21/M/J/18 Q9
9 Methylpropane is a saturated hydrocarbon.

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.

(i) One of these compounds has a relative molecular mass of 127.

What is the molecular formula of this compound?

molecular formula ......................................................

Suggest a structure for this compound. Show all of the atoms and all of the bonds.

[2]

(ii) Another compound formed has the percentage composition by mass:

29.7% carbon; 4.3% hydrogen; 65.9% chlorine.

Calculate the molecular formula for this compound.

molecular formula ..................................................[2]

© UCLES 2018 5070/21/M/J/18

Abul Fazal Organic Chemistry WS 2


64
19
18 5070/21/M/J/18 Q9
(iii) A compound is formed when one molecule of methylpropane reacts with five molecules
of chlorine.

alt
Write the molecular formula for this compound.

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

(b) The structures of propene and cyclopropane are shown.

H
H H H
C H
C C C
C H
H CH3 H
H
propene cyclopropane

These two compounds are isomers of each other.

(i) What is meant by the term isomerism?

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

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

(ii) Both compounds are hydrocarbons.

What is meant by the term hydrocarbons?

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

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

(iii) Propene is an unsaturated hydrocarbon and cyclopropane is a saturated hydrocarbon.

What is the difference between an unsaturated and a saturated hydrocarbon?

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

.......................................................................................................................................[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.

© UCLES 2018 5070/21/M/J/18

Organic Chemistry WS Abul Fazal


65
7
19 5070/22/M/J/18 Q5
5 Naphtha is a fraction obtained from petroleum (crude oil).

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.

Construct the equation for this reaction.

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

(c) Ethene, C2H4, can be made by cracking hydrocarbons.

You only need to show the outer shell electrons.

[2]

© UCLES 2018 5070/22/M/J/18 [Turn over

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66
8
19 5070/22/M/J/18 Q5
(d) Chlorine reacts with both ethene and ethane.

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.

What is the molecular formula of the organic product of this reaction?

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

[Total: 10]

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67
16
20 5070/22/M/J/18 Q10
10 Ester A has the structure shown.

alt
H O H H H H

H C C O C C C C H

H H H H H

(a) Name ester A.

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

(b) Ester A reacts with hot aqueous sodium hydroxide to give two compounds, B and C.

(i) Compound B has the percentage composition by mass:

29.3% carbon; 3.7% hydrogen; 39.0% oxygen; 28.0% sodium.

Calculate the empirical formula for this compound.

[2]

(ii) Compound C has a relative molecular mass of 74 and is oxidised by warm acidified
potassium manganate(VII) to give butanoic acid.

Suggest a structure for C.

Give reasons for your answer.

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

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

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

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

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68
17
21 5070/22/M/J/18 Q10
(c) (i) What is meant by the term isomerism?

alt
...........................................................................................................................................

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

(ii) Draw an isomer of ester A.

[1]

(d) Explain why ester A is a saturated compound.

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

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

(e) Ester A can be used as a fragrance or perfume because it diffuses easily.

(i) Explain why the rate of diffusion of the ester decreases as the temperature decreases.

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

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

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

(ii) Suggest one other use for ester A.

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

[Total: 10]

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69
5
22 5070/21/O/N/18 Q3
3 Tartaric acid and succinic acid are colourless organic acids.

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?

(c) Succinic acid is a weak acid.

What is the meaning of the term ?

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

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

(d) Succinic acid is neutralised by aqueous sodium hydroxide.

C2H4(COOH)2 + 2NaOH C2H4(COONa)2 + 2H2O

Calculate the minimum volume of 0.0200 mol / dm3 sodium hydroxide required to neutralise
25.0 cm3 of 0.0500 mol / dm3 succinic acid.

Give your answer to three significant figures.

volume ................................................... cm3 [3]

[Total: 7]
© UCLES 2018 5070/21/O/N/18 [Turn over

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70
6
23 5070/21/O/N/18 Q4
4 The alkanes are a homologous series of saturated hydrocarbons.

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.

Give one other characteristic of a homologous series.

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

(b) What is the meaning of the term ?

...............................................................................................................................................[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]

(e) Chlorine reacts with pentane.

C5H12 + Cl2 C5H11Cl + HCl

(i) What name is given to this type of chemical reaction?

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

(ii) What essential condition is needed for chlorine to react with pentane?

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

© UCLES 2018 5070/21/O/N/18

Organic Chemistry WS Abul Fazal


7

(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.

(i) Deduce the empirical formula of this hydrocarbon.

alt
empirical formula ...........................................................[2]

(ii) What additional piece of information is formula


empirical needed to deduce the molecular formula of this
...........................................................[2]
hydrocarbon?
(ii) What additional piece of information is needed to deduce the molecular formula of this
.......................................................................................................................................[1]
hydrocarbon?
[Total: 11]
.......................................................................................................................................[1]

[Total: 11]

© UCLES 2018 5070/21/O/N/18 [Turn over

© UCLES 2018 5070/21/O/N/18 [Turn over

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72

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]

(b) Fumaric acid is oxidised by acidified aqueous potassium manganate(VII).

What colour change would you observe in the reaction mixture when excess aqueous
fumaric acid is added to acidified aqueous potassium manganate(VII)?

from ............................................................... to ..................................................................[2]

(c) Fumaric acid is neutralised by aqueous sodium hydroxide.

C2H2(COOH)2 + 2NaOH C2H2(COONa)2 + 2H2O

(i) Write the ionic equation for this reaction.

.......................................................................................................................................[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.

Give your answer to three significant figures.

volume .................................................. cm3 [3]

[Total: 7]

© UCLES 2018 5070/22/O/N/18 [Turn over

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73

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]

(d) Butene reacts with hydrogen in the presence of nickel.

(i) Name the product formed.

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

(ii) What is the purpose of the nickel?

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

(iii) State one other condition needed for this reaction.

7
.......................................................................................................................................[1]

(e) A hydrocarbon contains 85.7% carbon by mass.

(i) Deduce the empirical formula of this hydrocarbon.

[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

(a) What is meant by the term hydrocarbon?

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

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

(b) Explain why cyclobutane and butene are isomers.

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

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

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

(c) Cyclobutane is saturated and butene is unsaturated.

Describe a chemical test that can distinguish cyclobutane from butene.

test ............................................................................................................................................

result for cyclobutane ...............................................................................................................

result for butene ........................................................................................................................


[3]

(d) Calculate the percentage by mass of carbon in butene.

percentage by mass ......................................................... [2]

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Organic Chemistry WS Abul Fazal


75
17
26 5070/21/M/J/19 Q10
(e) Ethene can be converted into ethanoic acid in a two-step process.

alt
H H H O
step 1 step 2
C C compound X H C C
H H H OH

(i) Identify compound X.

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

(ii) Identify the reagent used in step 1.

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

(iii) Identify the reagent used in step 2.

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

[Total: 10]

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Abul Fazal Organic Chemistry WS 2


76
16
27 5070/22/M/J/19 Q10
10 The structures of cyclobutanol and butanoic acid are shown.

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

(a) Explain why cyclobutanol is not a hydrocarbon.

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

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

(b) Explain why butanoic acid is a saturated compound.

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

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

(c) Describe a chemical test that can distinguish cyclobutanol from butanoic acid.

test ............................................................................................................................................

result for cyclobutanol ...............................................................................................................

result for butanoic acid .............................................................................................................


17 [3]

(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

(i) Identify compound X.


percentage by mass ......................................................... [2]

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

(ii) Identify the reagent used in step 1.

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

(iii) Identify the reagent used in step 2.

© UCLES 2019 .....................................................................................................................................


5070/22/M/J/19 [1]

Organic Chemistry WS [Total: 10]


Abul Fazal
The products are calcium ethanoate and hydrogen.

Construct the equation for this reaction. 77

............................................................................................................................................. [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]

(ii) Draw the structure of this ester.

[1]

[Total: 10]

© UCLES 2019 5070/21/O/N/19 [Turn over

Abul Fazal Organic Chemistry WS 2


(ii) Explain why aqueous magnesium chloride does not react with aqueous bromine.

..................................................................................................................................... [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.

In your answer include a description of fractional distillation in an oil refinery.

You may draw a labelled diagram.

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

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

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

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

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

5
............................................................................................................................................. [3]

(b) State one use for each of these hydrocarbon fractions:

kerosene ...................................................................................................................................

© UCLES 2019
naphtha .....................................................................................................................................
5070/22/O/N/19
[2]

(c) The refinery gas fraction contains methane, ethane and propane.

(i) To which homologous series do these hydrocarbons belong?

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

(ii) Give the general formula for the homologous series which contains methane, ethane
and propane.

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

(d) The exhaust from diesel engines contains carbon monoxide.

(i) Explain how carbon monoxide is formed in the diesel engine.


Organic Chemistry WS Abul Fazal
..................................................................................................................................... [1]

(ii) Describe one effect of carbon monoxide on human health.


Section B

Answer three questions from this section in the spaces provided.


79
The total mark for this section is 30.

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)

physical state: ...........................................................................................................................

explanation: ..............................................................................................................................

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

© UCLES 2019 5070/22/O/N/19

Abul Fazal Organic Chemistry WS 2


80

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

(a) These esters are part of a homologous series.

State two characteristics of a homologous series.

1. ...............................................................................................................................................

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

2. ...............................................................................................................................................

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

(b) The next member of the homologous series is hexyl ethanoate.

Explain why it is more difficult to predict the melting point than the boiling point of
hexyl ethanoate.

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

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

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

(c) At 25 °C ethyl ethanoate is a liquid.

Explain how the data in the table shows this.

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

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

(d) State one use for an ester.

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

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Organic Chemistry WS Abul Fazal


81

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

ethanoic acid carboxylic acid B

(a) An isomer of carboxylic acid B has the name methylpropanoic acid.

(i) What is the name of carboxylic acid B?

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

(ii) What is the meaning of the term isomer

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

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

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

(b) Vinegar contains ethanoic acid.

Describe the formation of vinegar from ethanol.

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

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

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

(c) Ethanoic acid reacts with calcium carbonate.

(i) Give the formula of the calcium salt formed in this reaction.

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

(ii) Name the other two products formed in this reaction.

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

[Total: 6]

© UCLES 2020 5070/21/M/J/20

Abul Fazal Organic Chemistry WS 2


82

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).

Choose from the list.

an alloy a compound an element

a mixture a polymer a salt

Petroleum (crude oil) is ................................................. of hydrocarbons. [1]

(b) Fractional distillation separates petroleum (crude oil) into fractions such as paraffin (kerosene)
and naphtha.

Give one use for the paraffin (kerosene) fraction.

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

(c) The naphtha fraction is used as a chemical feedstock.

One of the hydrocarbons in naphtha has the molecular formula C10H22.

The flow chart shows some compounds that can be made from C10H22.

cracking
C10H22 C 3H 8 + C3H6 + C 4H 8

Cl2 and uv light Br2 polymerisation

C3H7Cl C3H6Br2 poly(butene)

(i) C3H8 is an alkane and C3H6 is an alkene.

Explain why, in terms of their general formulae, C3H8 is an alkane and C3H6 is an alkene.

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

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

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

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

© UCLES 2020 5070/21/M/J/20

Organic Chemistry WS Abul Fazal


83
4 4
33 5070/22/M/J/20 Q3
3 3 The table
The shows
table some
shows properties
some of five
properties esters.
of five esters.

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.

(i) (i)State thethe


State relative molecular
relative mass
molecular of methyl
mass pentanoate.
of methyl pentanoate.

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


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

(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.

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

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


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

(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.

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

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


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

(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.

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


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

© UCLES 2020
© UCLES 2020 5070/22/M/J/20
5070/22/M/J/20

Abul Fazal Organic Chemistry WS 2


84
10
34 5070/22/M/J/20 Q6
6 The structures of two alcohols are shown.

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

(a) What is the name of alcohol B?

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

(b) Draw the structure of one other alcohol which is an isomer of B.

Show all of the atoms and all of the bonds.

[1]

(c) Ethanoic acid is produced by the oxidation of ethanol.

State the reagent for this reaction.

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

(d) Ethanol is a simple molecular compound.

Explain why liquid ethanol does not conduct electricity.

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

11
............................................................................................................................................. [1]

(e) Ethanol can be dehydrated to form ethene, C2H4.

Describe, using a dot-and-cross diagram, the bonding in a molecule of ethene.

Only include the outer shell electrons.

© UCLES 2020 5070/22/M/J/20

Organic Chemistry WS Abul Fazal


85
18
35 5070/22/M/J/20 Q10
10 Fractional distillation and cracking are important processes in the conversion of petroleum (crude
oil) into useful hydrocarbons.

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]

(ii) Describe the separation of petroleum (crude oil) by fractional distillation.

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

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

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

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

(iii) Give one use of the bitumen fraction.

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

(b) The naphtha fraction is used as a chemical feedstock.

One of the hydrocarbons in naphtha has the molecular formula C10H22.

Use the general formula for an alkane to show that C10H22 is an alkane.

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

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

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

© UCLES 2020 5070/22/M/J/20

Abul Fazal Organic Chemistry WS 2


Section B

Answer three questions from this section in the spaces provided.


86
The total mark for this section is 30.
36 5070/21/O/N/20 Q6
6 (a) The table shows some properties of five alcohols.

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.

A few drops of a strong acid are added to catalyse the reaction.

(i) What does the term strong mean, when applied to acids?

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

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

© UCLES 2020 5070/21/O/N/20

Organic Chemistry WS Abul Fazal


87
11
36 5070/21/O/N/20 Q6
(ii) Name and draw the structure of the ester produced when ethanol reacts with
butanoic acid, showing all of the atoms and all of the bonds.

alt
name .................................................................................................................................

structure

[2]

(c) Ethanol can be oxidised to ethanoic acid in the laboratory.

State the reagents and conditions used in this reaction.

reagent .....................................................................................................................................

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

(d) Concentrated ethanoic acid, CH3CO2H, reacts with calcium.

The products are calcium ethanoate and hydrogen.

(i) Construct the equation for this reaction.

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

(ii) State and explain how the rate of this reaction changes when the experiment is repeated
using dilute ethanoic acid.

All other conditions stay the same.

Include in your answer ideas about collisions between particles.

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

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

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

[Total: 10]

© UCLES 2020 5070/21/O/N/20 [Turn over

Abul Fazal Organic Chemistry WS 2


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

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

© UCLES 2020 5070/22/O/N/20 [Turn over


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

(ii) What type of chemical reaction is this?

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

(e) The table shows some properties of four carboxylic acids.

carboxylic acid formula density boiling point


in g / cm3 in °C
methanoic acid HCO2H 1.22 101
ethanoic acid CH3CO2H 118
propanoic acid C2H5CO2H 0.99 141
butanoic acid C3H7CO2H 0.96 164

(i) Predict the density of ethanoic acid.

.......................................................................................................................... g / cm3 [1]

(ii) Describe and explain the change in the boiling point as the number of carbon atoms in a
molecule increases.

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

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

[Total: 10]

Organic Chemistry WS Abul Fazal


32
7.2 The Periodic Table of Elements Appendix

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

Cambridge O Level Chemistry 5070. Syllabus for examination in 2022.


133 137 178 181 184 186 190 192 195 197 201 204 207 209 – – –
87 88 89–103 104 105 106 107 108 109 110 111 112 114 116
actinoids
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Fl Lv
francium radium rutherfordium dubnium seaborgium bohrium hassium meitnerium darmstadtium roentgenium copernicium flerovium livermorium
– – – – – – – – – – – – –

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

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