Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

 Petroleum and its products

 Names and formulae of organic compounds
 Structural formulae, homologous series and isomerism
 Characteristic reactions of different homologous series
 Chemistry of ethanol
 Carboxylic acids and esters
 Polymers
 Plastics

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

1) May 2016 [41] Q (6)

6 Petroleum is a source of many important chemicals.
(a) Name two industrial processes which must take place to produce alkenes
from petroleum.
............................................................................................................................
....................................................................................................................... [2]
(b) Ethene, CH2=CH2, and propene, CH2=CHCH3, can both be converted into
polymers.
(i) What type of polymerisation takes place when ethene forms a polymer?
....................................................................................................................... [1]
(ii) What is the empirical formula of the polymer formed from ethene?
....................................................................................................................... [1]
(iii) Propene has the structural formula CH2=CHCH3.
Draw two repeat units of the polymer made from propene.

[2]
(c) Ethene will react with steam to form ethanol.
Propene will react with steam to form two isomers, both of which are alcohols.
Suggest the structures of these alcohols.

[2]
(d) Esters are organic chemicals noted for their characteristic smells. Ethanoic
acid and methanol will react to form an ester.
(i) Name the catalyst needed to form an ester from ethanoic acid and
methanol.
....................................................................................................................... [1]
(ii) Name the ester formed when ethanoic acid reacts with methanol.
....................................................................................................................... [1]
(iii) Draw the structure of the ester formed when ethanoic acid reacts with
methanol. Show all bonds.

[2]
(iv) Give the name of a polyester.
....................................................................................................................... [1]
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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

2) May 2016 [42] Q (5)

5 (a) Hydrocarbons are compounds which contain hydrogen and carbon only.
• 10 cm3 of a gaseous hydrocarbon, CxHy, are burned in 100 cm3 of
oxygen, which is an excess of oxygen.
• After cooling to room temperature and pressure, there is 25 cm3 of
unreacted oxygen, 50 cm3 of carbon dioxide and some liquid water.
All volumes are measured under the same conditions of temperature and
pressure.
(i) What is meant by an excess of oxygen?
....................................................................................................................... [1]
(ii) What was the volume of oxygen that reacted with the hydrocarbon?
....................................................................................................................... [1]
(iii) Complete the table below to express the smallest whole number ratio of

volume of
volume of volume of
: : carbon dioxide
hydrocarbon reacted oxygen reacted
produced

volume of
volume of volume of
carbon dioxide
hydrocarbon reacted oxygen reacted
produced

smallest whole
number ratio of
volumes

[1]
(iv) Use your answer to (a)(iii) to find the mole ratio in the equation below.
Complete the equation and deduce the formula of the hydrocarbon.
.........C xHy(g) + .........O2(g) 
→ .........CO2(g) + .........H2O(l)

formula of hydrocarbon = ...........................................

[2]
(b) Cracking is used to convert long chain alkanes into shorter chain alkanes
and alkenes. Alkenes are unsaturated compounds.
Decane, C10H22, can be cracked to give propene and one other product.
(i) Complete the chemical equation.
C10H22 
→ C3H6 + ...............
[1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(ii) What is meant by the term unsaturated?

....................................................................................................................... [1]
(iii) Describe a test to show that propene is an unsaturated compound.
test .....................................................................................................................
result ..................................................................................................................
[2]
(c) Propene can be polymerised. The only product is polypropene. The
equation for the polymerisation is:

(i) Name the type of polymerisation that occurs.

....................................................................................................................... [1]
(ii) Deduce the maximum mass of polypropene that could be produced from 1
kg of propene.
............... kg [1]
(iii) Give the empirical formula of
propene, .............................................................................................................
polypropene. ......................................................................................................
[2]
3) May 2016 [43] Q (2)
2 The structures of six organic compounds are shown.

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(a) Give the name of F.

....................................................................................................................... [1]
(b) Identify two of the compounds that are members of the same homologous
series.
Give the general formula of this homologous series.
compounds ........................................................................................................
general formula ..................................................................................................
[2]
(c) Which two compounds are isomers of each other?
Explain why they are isomers.
compounds ........................................................................................................
explanation .........................................................................................................
............................................................................................................................
[3]
(d) Explain why B is an unsaturated hydrocarbon.
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(e) Describe how D is manufactured from B. Give a chemical equation for the
reaction.
............................................................................................................................
............................................................................................................................
....................................................................................................................... [3]
(f) Compound A forms an addition polymer.
Draw two repeat units of the addition polymer formed from A.

[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

4) May 2016 [43] Q (6_d, e)

(d) Nylon and proteins are both polymers containing nitrogen.
(i) Name the linkages found in the polymers of nylon and protein.
....................................................................................................................... [1]
(ii) Describe one difference in the structures of nylon and protein.
....................................................................................................................... [1]
(iii) What is the general name given to the products of hydrolysis of proteins?
....................................................................................................................... [1]
(e) Suggest the structure of the monomer used to make the polymer shown.

[1]
5) Nov 2016 [41] Q (3_a, b, c, d, e, i)
3 (a) Petroleum is a mixture of hydrocarbons. It is separated into useful
fractions by fractional distillation. This can be done using the fractionating
column shown.

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(i) What happens to the petroleum at point X, before it enters the fractionating
column?
............................................................................................................................
....................................................................................................................... [1]
(ii) State two ways in which fraction O differs from fraction L.
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(b) Most of the hydrocarbons obtained from petroleum are alkanes. The
alkanes are an homologous series of saturated hydrocarbons with the general
formula CnH2n+2.
Give two characteristics, other than having the same general formula, of
members of an homologous series.
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(c) The alkane with the molecular formula C5H12 can exist as a number of
structural isomers.
Draw the structures of two isomers with the formula C5H12.

[2]
(d) The alkane ethane has the structure shown.

When a mixture of ethane and chlorine is exposed to ultraviolet light a

substitution reaction takes place.
Draw the structure of one organic product from this substitution reaction.

[1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(e) Isoprene is a naturally occurring hydrocarbon.

(i) Explain how the name of isoprene suggests that it contains a C=C double
bond.
....................................................................................................................... [1]
6) Nov 2016 [41] Q (6)
6 Nylon, Terylene and proteins are all polymers.
(a) What is a polymer?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(b) Proteins are natural polymers. Proteins are biodegradable.
(i) Name the type of linkage in proteins.
....................................................................................................................... [1]
(ii) What is meant by the term biodegradable?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(c) Nylon and Terylene are synthetic polymers.
The repeat unit of nylon can be shown as

Terylene can be made from the monomers shown.

Draw a diagram to show the repeat unit of Terylene.

[3]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

7) Nov 2016 [42] Q (5_c, d)

(c) When one mole of bromine, Br2, reacts with one mole of propene, one
organic product is formed.
(i) Which part of the propene molecule reacts with bromine?
....................................................................................................................... [1]
(ii) What is the name of the type of reaction which takes place between
bromine and propene?
....................................................................................................................... [1]
(d) When one mole of chlorine, Cl2, reacts with one mole of propane, a
mixture of two structural isomers is formed.
(i) What is the name of the type of reaction which takes place between
chlorine and propane?
....................................................................................................................... [1]
(ii) Explain what is meant by the term structural isomers.
............................................................................................................................
....................................................................................................................... [2]
(iii) Draw the structure of two structural isomers formed when one mole of
chlorine reacts with one mole of propane.

[2]
8) Nov 2016 [42] Q (7_a, d)
7 Proteins are a major constituent of food.
Proteins are polymers.
(a) What is a polymer?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(d) When one molecule of an amino acid A combines with one molecule of
another amino acid B, two different dipeptide molecules could be formed.
Draw the structures of the two different dipeptide molecules.
Show all of the atoms and all of the bonds in the linkages.

[3]
9) Nov 2016 [43] Q (6_a, b, d)
6 Synthetic polyamides are made by condensation polymerisation.
(a) (i) What is meant by the term condensation polymerisation?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [3]
(ii) Name another type of polymerisation.
....................................................................................................................... [1]
(b) One repeat unit of a synthetic polyamide is represented by the following
structure.

(i) Draw a ring around the amide link. [1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(ii) Complete the diagrams to show the structures of the monomers used to
produce the synthetic polyamide. Show all the missing atoms and bonds.

[2]
(iii) Name an example of a synthetic polyamide.
....................................................................................................................... [1]
(c) Proteins and synthetic polyamides have similarities and differences.
(i) Name the type of compounds that are the monomers used to make up
proteins.
....................................................................................................................... [1]
(ii) Starting with a sample of protein, describe how to produce, separate,
detect and identify the monomers which make it up.
Your answer should include
• the name of the process used to break down the protein into its monomers,
• the name of the process used to separate the monomers,
• the method used to detect the monomers after they have been separated,
• the method used to identify the monomers after they have been separated.
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [4]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

10) May 2017 [41] Q (6)

6 The alkenes and alkanes are both examples of homologous series which
are hydrocarbons.
(a) What is meant by the term hydrocarbon?
............................................................................................................................
....................................................................................................................... [2]
(b) Give three characteristics of an homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
3 .........................................................................................................................
[3]
(c) Name and draw the structure of the second member of the alkene
homologous series.
Show all of the atoms and all of the bonds.
name ..................................................................................................................
structure

[2]
(d) Alcohols can be made from alkenes.
Name the reagent and conditions needed to convert an alkene into an
alcohol.
............................................................................................................................
....................................................................................................................... [2]
(e) The alcohol butanol, CH3CH2CH2CH2OH, can be converted into a
carboxylic acid with four carbon atoms.
(i) Name the carboxylic acid formed from butanol and draw its structure. Show
all of the atoms and all of the bonds.
name ..................................................................................................................
structure

[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(ii) Ethanoic acid can be formed from ethanol by fermentation. It can also be
formed by the addition of a suitable chemical reagent.
Name the reagent needed to convert ethanol into ethanoic acid.
....................................................................................................................... [2]
(iii) State the type of chemical change which occurs when ethanol is
converted into ethanoic acid.
....................................................................................................................... [1]
(f) Describe how a student could prepare the ester methyl ethanoate in a
school laboratory.
In your description give
● the names of the two starting organic chemicals,
● the essential reaction conditions needed,
● a chemical equation for the reaction.
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [5]
11) May 2017 [42] Q (6)
6 (a) An homologous series is a ‘family’ of organic compounds whose names
have the same ending.
(i) Name the homologous series for which the names of the organic
compounds end in –ene and –oic acid.
–ene ...................................................................................................... [1]
–oic acid ............................................................................................... [1]
(ii) State two characteristics of an homologous series.
............................................................................................................................
....................................................................................................................... [2]
(b) Propan-1-ol is a member of the homologous series of alcohols. It reacts in
the same way as ethanol with acidified potassium manganate(VII) and with
carboxylic acids.
Name the type of compound that is formed when propan-1-ol is heated with
acidified potassium manganate(VII), ..................................................................
ethanoic acid and a suitable catalyst. ................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(c) The structure of prop-2-enoic (acrylic) acid is shown.

(i) What would you see if prop-2-enoic acid were added to

aqueous bromine, ..............................................................................................
a solution of sodium carbonate. .........................................................................
[2]
(ii) Prop-2-enoic acid can be polymerised to form poly(acrylic acid).
Suggest the type of polymerisation that occurs and draw one repeat unit of
the polymer.
type of polymerisation ...................................................................
repeat unit

[3]
12) May 2017 [43] Q (2_a)
2 Cyclopropane is a colourless gas.
Cyclopropane reacts with bromine at room temperature. The chemical
equation for the reaction is shown.

(a) (i) What is the empirical formula of cyclopropane?

....................................................................................................................... [1]
(ii) What colour change, if any, would you see when cyclopropane is bubbled
into aqueous bromine?
initial colour ........................................................................................................
final colour ..........................................................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

13) May 2017 [43] Q (4_a, b, d)

4 Gasoline is used as a fuel for cars. It is a mixture of hydrocarbons.
(a) Name the raw material from which gasoline is obtained.
....................................................................................................................... [1]
(b) One of the compounds in gasoline is heptane, C7H16. Heptane is a
saturated hydrocarbon.
(i) What is meant by the term saturated hydrocarbon?
saturated ............................................................................................................
............................................................................................................................
hydrocarbon .......................................................................................................
............................................................................................................................
[3]
(ii) To which homologous series does heptane belong?
....................................................................................................................... [1]
(iii) Give two characteristics of an homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(iv) Complete the chemical equation for the complete combustion of heptane.
C7H16 + ..........O2 
→ ....................... + .......................
[2]
(d) The formula C4H10 represents two structural isomers, A and B.

(i) Name isomer A.

....................................................................................................................... [1]
(ii) What is meant by the term structural isomers?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(iii) Isomer B reacts with chlorine in a substitution reaction.

Give the conditions required for the reaction to occur and draw the structures
of two possible products, one of which is organic and one of which is not
organic.
conditions ...........................................................................................................
structures of products

[3]
14) Nov 2017 [41] Q (4_a, b, c, i, e)
4 (a) Ethanol, C2H5OH, can be made by fermentation.
(i) Complete the chemical equation for the formation of ethanol by
fermentation.
C6H12O6 
→ ......C2H5OH + ..............................
[2]
(ii) State two conditions required for fermentation.
1 .........................................................................................................................
2..........................................................................................................................
[2]
(b) Ethanol can also be made by the catalytic hydration of ethene. The
equation for the reaction is shown.
C2H4 + H2O 
→ C2H5OH
(i) Name a suitable catalyst for this reaction.
....................................................................................................................... [1]
(ii) Calculate the maximum mass of ethanol that can be made from 56 g of
ethene.

maximum mass of ethanol = ......................... g [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

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

(i) Name a suitable oxidising agent for this reaction.
....................................................................................................................... [1]
(e) Carboxylic acids react with alcohols to make esters.
The structure of an ester is shown.

Draw the structures of the carboxylic acid and alcohol from which this ester
can be made.
Give the names of the carboxylic acid and alcohol.
structure of the carboxylic acid

name of the carboxylic acid

........................................................................................................
structure of the alcohol

name of the alcohol

....................................................................................................................
[4]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

15) Nov 2017 [42] Q (3_d, e, f)

(d) Dodecane is an alkane containing 12 carbon atoms. Ethanol can be
manufactured from dodecane in a two-stage process.
In stage 1, each molecule of dodecane is converted into three molecules of
ethene and one molecule of another hydrocarbon.
(i) Name the process which occurs in stage 1.
....................................................................................................................... [1]
(ii) Write a chemical equation for the reaction which occurs in stage 1.
....................................................................................................................... [2]
In stage 2, ethene reacts with steam to produce ethanol.
(iii) State two conditions needed for stage 2.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(iv) Name the type of reaction which occurs in stage 2.
....................................................................................................................... [1]
(v) Suggest how to test the purity of the ethanol produced.
............................................................................................................................
....................................................................................................................... [2]
(e) Ethanol can also be manufactured by the fermentation of glucose,
C6H12O6.
(i) State two conditions needed for the fermentation of glucose.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(ii) Complete the chemical equation for the fermentation of glucose.
C6H12O6 
→ ......C2H5OH + ..............................
[2]
(iii) One disadvantage of fermentation is that the maximum concentration of
ethanol produced is about 15%.
Suggest why the concentration of ethanol produced by fermentation does not
exceed 15%.
............................................................................................................................
....................................................................................................................... [1]
(iv) Give one other disadvantage of manufacturing ethanol by fermentation.
....................................................................................................................... [1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(v) Give one advantage, other than cost, of manufacturing ethanol by

fermentation.
....................................................................................................................... [1]
(vi) Suggest the name of a process to obtain ethanol from a mixture of
ethanol and water.
....................................................................................................................... [1]
(f) Ethane-1,2-diol has the following structure.

(i) Write the empirical formula of ethane-1,2-diol.

....................................................................................................................... [1]
(ii) Ethane-1,2-diol can undergo condensation polymerisation but cannot
undergo addition polymerisation.
Explain why ethane-1,2-diol cannot undergo addition polymerisation.
............................................................................................................................
....................................................................................................................... [1]
(iii) Ethane-1,2-diol undergoes condensation polymerisation with molecule Y.
The diagrams represent the structures of ethane-1,2-diol and molecule Y.

Draw the condensation polymer formed between ethane-1,2-diol and

molecule Y.
Show one repeat unit. Show all of the atoms and all of the bonds in the
linkage.

[3]
(iv) Name the type of condensation polymer formed between ethane-1,2-diol
and molecule Y.
....................................................................................................................... [1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

16) Nov 2017 [43] Q (4_e)

(e) Some fuel cells use ethanol, C2H5OH, instead of hydrogen. Carbon dioxide
and water are products of the reaction in an ethanol fuel cell.
(i) Write a chemical equation for the overall reaction occurring in an ethanol
fuel cell.
....................................................................................................................... [2]
(ii) State an environmental problem caused by the release of carbon dioxide
into the atmosphere.
....................................................................................................................... [1]
(iii) Name the process by which ethanol can be manufactured from a
renewable resource.
....................................................................................................................... [1]
(f) Name the process occurring when electrical energy is used to break down
an ionic compound.
....................................................................................................................... [1]
17) Nov 2017 [43] Q (6)
6 (a) Alkanes and alkenes are two homologous series of hydrocarbons.
(i) What is meant by the term hydrocarbon?
....................................................................................................................... [1]
(ii) What is the general formula of the homologous series of
alkanes, ..............................................................................................................
alkenes? .............................................................................................................
[2]
(iii) Other than having a general formula, state two characteristics of a
homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(iv) The structure of an alkene molecule with the molecular formula C4H8 is
shown.

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

Draw the structure of a different alkene molecule with the molecular formula
C4H8. Show all of the atoms and all of the bonds.

[1]
(v) What term describes molecules with the same molecular formula but
different structural formulae?
....................................................................................................................... [1]
(b) 25 cm3 of a gaseous hydrocarbon, CxHy, were burnt in 150 cm3 of oxygen.
This was an excess of oxygen.
After cooling, the volume of the gases remaining was 100 cm3. This consisted
of 75 cm3 of carbon dioxide and 25 cm3 of unreacted oxygen. The water that
was produced in the reaction was liquid.
All volumes were measured at the same temperature and pressure.
(i) What is meant by an excess of oxygen?
....................................................................................................................... [1]
(ii) What was the volume of oxygen that reacted with the hydrocarbon?
............................. cm3 [1]
(iii) Complete the table to show the smallest whole number ratio of volumes.

[1]
(iv) Use your answer to (b)(iii) to balance the chemical equation. Deduce the
formula of the hydrocarbon.
CxHy(g) + ......O2(g) 
→ ......CO2(g) + ......H2O(l)

formula of the hydrocarbon = ............................. [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

18) May 2018 [41] Q (6)

6 The table shows the structures of four hydrocarbons.

(a) Why are compounds P, Q, R and S known as hydrocarbons?

............................................................................................................................
....................................................................................................................... [2]
(b) Compound P is saturated.
What is meant by the term saturated?
............................................................................................................................
....................................................................................................................... [1]
(c) Compound P undergoes a substitution reaction with chlorine.
(i) What is meant by the term substitution reaction?
............................................................................................................................
....................................................................................................................... [1]
(ii) State a condition required for this reaction to occur.
....................................................................................................................... [1]
(iii) Write a chemical equation for this reaction.
....................................................................................................................... [2]
(d) Compound R undergoes an addition reaction with bromine.
(i) Why is this reaction an addition reaction?
....................................................................................................................... [1]
(ii) A compound containing bromine is formed in this reaction.
Draw the structure of this compound. Show all of the atoms and all of the
bonds.

[1]
(e) Draw the structure of an unbranched isomer of compound S. Show all of
the atoms and all of the bonds. Name this unbranched isomer of compound S.
structure

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

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(f) Compound Q undergoes polymerisation.

(i) Name the polymer formed.
....................................................................................................................... [1]
(ii) Complete the chemical equation to show the polymerisation of compound
Q.

n CH2=CH2 
→

[2]
(g) Amino acids undergo polymerisation to form proteins. Part of a protein
molecule with the linkages missing is shown.
Draw the linkages on the diagram. Show all of the atoms and all of the bonds.

[2]

(h) The structure shows an ester.

Write the word equation for a reaction which could be used to make this ester.
....................................................................................................................... [3]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

19) May 2018 [42] Q (7_c, d, e, f)

(c) Compounds T and V both have the molecular formula C3H6O2.
● Compound T produces bubbles of carbon dioxide gas when it is added to
aqueous sodium carbonate.
● Compound V is an ester.
(i) What is the name given to compounds with the same molecular formula but
different structures?
....................................................................................................................... [1]
(ii) Draw the structures of compounds T and V. Show all of the atoms and all
of the bonds.
compound T

compound V

[2]
(iii) All compounds with the molecular formula C3H6O2 can undergo complete
combustion in an excess of oxygen.
Complete the chemical equation for this reaction.
C3H6O2 + ................... 
→ .................... + ...................
[2]
(d) Compound W has the molecular formula C2H6O. Compound W reacts
when heated with ethanoic acid and a catalyst to produce a sweet‑smelling
liquid.
(i) Give the name of the homologous series to which compound W belongs.
....................................................................................................................... [1]
(ii) Draw the structure of compound W. Show all of the atoms and all of the
bonds.

[1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(e) Alkanes and alkenes are hydrocarbons.

(i) What is meant by the term hydrocarbon?
............................................................................................................................
....................................................................................................................... [2]
(ii) State the general formula of:
alkanes ...............................................................................................................
alkenes ...............................................................................................................
[2]
(f) Ethanol can be produced from long‑chain alkanes as shown.

Describe the two‑stage manufacture of ethanol from the long‑chain alkane

octane, C8H18.
Include:
● the names of the types of chemical reactions that occur
● reaction equations
● reaction conditions.
step 1 .................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
step 2 .................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [5]

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20) May 2018 [43] Q (4)

4 Ethanol is a member of the homologous series of alcohols.
(a) Give two characteristics of members of a homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(b) The structure of ethanol is shown.

Complete the dot‑and‑cross diagram to show the electron arrangement in a

molecule of ethanol. Show outer shell electrons only.

[2]
(c) Ethanol can be produced by the catalytic addition of steam to ethene or by
the fermentation of glucose.
(i) Write a chemical equation for the production of ethanol by the catalytic
addition of steam to ethene.
....................................................................................................................... [1]
(ii) Write a chemical equation for the production of ethanol by the fermentation
of glucose, C6H12O6.
....................................................................................................................... [1]
(iii) State one advantage of producing ethanol by the catalytic addition of
steam to ethene.
Your answer must not refer to cost.
....................................................................................................................... [1]

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(iv) State one advantage of producing ethanol by the fermentation of glucose.

Your answer must not refer to cost.
....................................................................................................................... [1]
(d) Ethanol can be oxidised to ethanoic acid.
State the chemical reagent needed to oxidise ethanol to ethanoic acid.
....................................................................................................................... [1]
(e) Ethanoic acid reacts with ethanol in the presence of an acid catalyst. The
products are an organic compound and water.
(i) Draw the structure of the organic compound formed. Show all of the atoms
and all of the bonds.

[2]
(ii) State the name of the organic compound formed.
....................................................................................................................... [1]
(iii) Which homologous series does the organic compound formed belong to?
....................................................................................................................... [1]
(f) Ethanoic acid, CH3COOH, is a weak acid. It reacts with copper(II)
carbonate to form the salt copper(II) ethanoate, Cu(CH3COO)2.
(i) What is meant by the term weak when applied to acids?
....................................................................................................................... [1]
(ii) Describe how a crystalline sample of copper(II) ethanoate can be prepared
starting with ethanoic acid and copper(II) carbonate.
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [3]
(iii) Write the word equation for the reaction between ethanoic acid and
copper(II) carbonate.
....................................................................................................................... [1]

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21) Nov 2018 [41] Q (6)

6 (a) Ethane, C2H6, is a member of the homologous series called alkanes.
Ethanol, C2H5OH, is a member of the homologous series called alcohols.
(i) Alkanes are hydrocarbons.
What is meant by the term hydrocarbon?
............................................................................................................................
....................................................................................................................... [2]
(ii) All members of a homologous series can be represented by a general
formula.
State the general formula of:
● alkanes ...........................................................................................................
● alcohols ...........................................................................................................
[2]
(iii) State two characteristics, other than having the same general formula, of
members of a homologous series.
1 .........................................................................................................................
............................................................................................................................
2 .........................................................................................................................
............................................................................................................................
[2]
(b) Ethane can react with chlorine in a substitution reaction.
(i) State one essential reaction condition.
....................................................................................................................... [1]
(ii) Draw the structure of the organic product formed by substitution of one of
the hydrogen atoms in ethane with chlorine. Show all of the atoms and all of
the bonds.

[1]
(iii) Name the product of the substitution reaction between ethane and
chlorine that does not contain carbon.
....................................................................................................................... [1]

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(c) Propan-1-ol is an alcohol.

The structure of propan-1-ol is shown.

Propan-1-ol reacts with ethanoic acid to form an ester.

Give the name of the ester formed in this reaction.
....................................................................................................................... [1]
(d) Ester Y has the structure shown.

(i) Give the molecular formula of ester Y.

....................................................................................................................... [1]
(ii) Draw the structures of the carboxylic acid and the alcohol used to make
ester Y. Show all of the atoms and all of the bonds. Give the name of the
carboxylic acid and the alcohol.
structure of the carboxylic acid

name of the carboxylic acid ...............................................................................

structure of the alcohol

name of the alcohol ............................................................................................

[4]

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(e) Nylon is a polyamide.

Complete the diagram to show the structure of nylon. Show all of the atoms
and all of the bonds present in the linkages.

[3]
22) Nov 2018 [42] Q (5)
5 Alkynes are a homologous series of unsaturated hydrocarbons.
All members contain a C≡C triple bond.
(a) Complete the table showing information about the first three alkynes.

[2]
(c) Compounds in the same homologous series have the same general
formula.
(i) Give two other characteristics of members of a homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(ii) Use the information in the table in (a) to deduce the general formula of
alkynes.
....................................................................................................................... [1]
(d) Alkynes are unsaturated.
Describe a test for unsaturation.
test .....................................................................................................................
result ..................................................................................................................
[2]
(e) (i) Name an oxidising agent which can be used to oxidise ethanol to
ethanoic acid.
....................................................................................................................... [2]

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(ii) Draw the structure of ethanoic acid. Show all of the atoms and all of the
bonds.
[1]

(f) Carboxylic acids can be converted into esters.

(i) The ester formed by reacting propanoic acid and methanol has the
molecular formula C4H8O2.
Name this ester and draw its structure. Show all of the atoms and all of the
bonds.
name of the ester ...............................................................................................
structure of the ester

[2]
(ii) Name another ester with the molecular formula C4H8O2.
....................................................................................................................... [1]
(g) Polyesters are polymers.
(i) What type of polymerisation is used in the manufacture of polyesters?
....................................................................................................................... [1]
(ii) Name a polyester.
....................................................................................................................... [1]
23) Nov 2018 [43] Q (6)
6 (a) Ethanol can be manufactured by fermentation and by hydration.
(i) Describe these two processes of ethanol manufacture.
In each case you should:
● identify the reactants
● give the reaction conditions
● write a chemical equation for the reaction which produces ethanol.
fermentation .......................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................

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hydration ............................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
[6]
(ii) Give two advantages of ethanol manufacture by fermentation compared to
by hydration.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(iii) State two major uses of ethanol.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(b) The structures of some polymers are shown.

Answer the following questions about these polymers.

Each polymer may be used once, more than once or not at all.
State which polymer, A, B, C, D or E, represents:
(i) an addition polymer .................................................................................. [1]
(ii) a protein ................................................................................................... [1]

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(iii) a polyester made from only one monomer ............................................. [1]

(iv) Terylene................................................................................................... [1]
24) May 2019 [41] Q (5)
5 The structures of five alkenes, A, B, C, D and E, are shown.

(a) What is the general formula of alkenes?

....................................................................................................................... [1]
(b) What is the molecular formula of alkene D?
....................................................................................................................... [1]
(c) Predict which alkene, A, B, C, D or E, has the highest boiling point.
Explain your answer.
alkene ……………….
explanation ……………………………………………………………………………
…………………………………………………………………………………………..
[2]
(d) Which alkene, A, B, C, D or E, diffuses most quickly?
Explain your answer.
alkene ……………….
explanation ……………………………………………………………………………
…………………………………………………………………………………………..
[2]

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(e) A student added aqueous bromine to alkene C.

Describe the colour change seen and draw the structure of the product. Show
all of the atoms and all of the bonds.
colour change from.............................................. to ………………..…………….
structure

[2]
(f) Two different alcohols can be produced from alkene B by an addition
reaction.

(i) Draw the structures of the two alcohols. Show all of the atoms and all of the
bonds.

[2]
(ii) State the reagent and conditions needed to produce an alcohol from
alkene B.
reagent ………………………………………………………………………………...
conditions ……………………………………………………………………………..
………………………………………..…………………………………………………
[3]

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(g) Alkene C can be converted into a polymer.

(i) What type of polymerisation occurs?

....................................................................................................................... [1]
(ii) Suggest the name of the polymer formed.
....................................................................................................................... [1]
(iii) Complete the chemical equation to show this polymerisation.

[3]
(iv) State the empirical formula of the polymer formed .
....................................................................................................................... [1]
25) May 2019 [42] Q (4_c, d)
(c) Methanol is a member of the homologous series of alcohols.
(i) State two general characteristics of a homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(ii) Draw the structures of two different alcohols, each containing three
carbon atoms. Show all of the atoms and all of the bonds.
Name these two alcohols.

[4]

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(iii) What term is used to describe compounds with the same molecular
formula but different structural formulae?
....................................................................................................................... [1]
(d) Alcohols react with carboxylic acids to produce esters.
(i) The structure of ester X is shown.

Name ester X.
....................................................................................................................... [1]
(ii) Give the name of the carboxylic acid and the alcohol that react together to
produce ester X.
carboxylic acid ...................................................................................................
alcohol ................................................................................................................
[2]
(iii) Ester Y is different from ester X but also has the formula C3H6O2.
Draw the structure of ester Y. Show all of the atoms and all of the bonds.

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

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26) May 2019 [43] Q (5_a)

5 Carboxylic acids react with alcohols to form esters. The reaction is
reversible.
The equation for the reaction between ethanoic acid and ethanol is shown.
 CH3COOCH2CH3 + H2O
CH3COOH + CH3CH2OH 
(a) (i) What is the name of the ester formed in this reaction?
....................................................................................................................... [1]
(ii) Draw the structure of the ester formed. Show all of the atoms and all of the
bonds.

[1]
27) May 2019 [43] Q (6)
6 (a) Two hydrocarbons have the structures shown.

(i) Why are these two compounds hydrocarbons?

............................................................................................................................
....................................................................................................................... [2]
(ii) Hydrocarbon B reacts in the same way as a typical alkane.
Describe a chemical test to tell the difference between hydrocarbon A and
hydrocarbon B.
State the name of the reagent you would use and the result you would obtain
with hydrocarbon A and hydrocarbon B.
reagent ...............................................................................................................
result with hydrocarbon A ..................................................................................
result with hydrocarbon B ..................................................................................
[3]

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(b) Alkenes react with steam to form alcohols.

Compound C is an alcohol.

Draw the structure of the alkene which could be reacted with steam to make
compound C. Show all of the atoms and all of the bonds.

[1]
(c) Alkenes can form polymers.
(i) What type of polymerisation occurs when alkenes form polymers?
....................................................................................................................... [1]
(ii) Part of the structure of a polymer is shown.

Draw the structure of the alkene from which this polymer can be made. Show
all of the atoms and all of the bonds.

[1]
(iii) Polymers can undergo incomplete combustion to form carbon monoxide.
Complete the chemical equation for the incomplete combustion of
poly(ethene). The only carbon‑containing product is carbon monoxide.

[2]

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(d) Part of the structure of a polyamide is shown.

This polyamide is formed from identical monomers. Complete the diagram to

show the structure of one monomer. Show all of the atoms and all of the
bonds.

[2]
28) Nov 2019 [41] Q (5)
5 (a) Part of the structure of synthetic polymer A is shown.

(i) What type of synthetic polymer is A?

....................................................................................................................... [1]
(ii) Deduce the empirical formula of polymer A.
....................................................................................................................... [1]
(iii) Draw the structure of the monomer from which polymer A is made.
[2]

(b) The formula C4H10 represents two different structural isomers.

(i) What is meant by the term structural isomers?
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]

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(ii) Draw the structures of two structural isomers with the formula C4H10.
Show all of the atoms and all of the bonds.
[2]

(iii) All structural isomers of C4H10 are flammable.

Write a chemical equation for the incomplete combustion of C4H10.
....................................................................................................................... [2]
29) Nov 2019 [41] Q (7_a)
7 This question is about ethanol.
(a) Ethanol that is suitable for use as a fuel can be manufactured from sugars
such as glucose, C6H12O6, by a two-step process.
Describe how this can be done. In your answer, include:
● an equation for the reaction in which ethanol is formed
● the essential conditions for the reaction in which ethanol is formed
● the name of the process used to obtain ethanol that is pure enough to use
as a fuel from the reaction mixture.
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [5]

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30) Nov 2019 [42] Q (2_f)

(f) CO is formed from the incomplete combustion of fossil fuels such as
methane.
Write a chemical equation to show the incomplete combustion of methane.
....................................................................................................................... [2]
31) Nov 2019 [42] Q (5_a, c)
5 Methanol, CH3OH, is a member of the homologous series of alcohols.
(a) Methanol can be made from methane in a two-step process.
step 1 Methane is reacted with chlorine gas to produce chloromethane,
CH3Cl.
step 2 CH3Cl is reacted with sodium hydroxide to produce CH3OH and one
other product.
(i) What conditions are needed in step 1?
....................................................................................................................... [1]
(ii) Write the chemical equation for the reaction which occurs in step 1.
....................................................................................................................... [1]
(iii) State the type of organic reaction occurring in step 1.
....................................................................................................................... [1]
(iv) Complete the chemical equation for step 2.
CH3Cl + NaOH 
→ CH3OH + ..............................
[1]
(c) Methanol reacts with propanoic acid to form an ester with a molecular
formula C4H8O2.
(i) Name the ester formed when methanol reacts with propanoic acid.
....................................................................................................................... [1]
(ii) Name one other substance formed when methanol reacts with propanoic
acid.
....................................................................................................................... [1]
(iii) Draw the structure of an ester which is a structural isomer of the ester
named in (c)(i).
Show all of the atoms and all of the bonds.

[3]

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(iv) State the conditions needed to form an ester from a carboxylic acid and
an alcohol.
....................................................................................................................... [1]
32) Nov 2019 [43] Q (7)
7 Addition polymerisation and condensation polymerisation are two types of
polymerisation.
(a) Which functional group is present in all the monomers which are used to
make addition polymers?
....................................................................................................................... [1]
(b) Part of an addition polymer is shown.

(i) How many monomer units are needed to make the part of the addition
polymer shown?
....................................................................................................................... [1]
(ii) Draw the structure of the monomer that is used to make this addition
polymer. Show all of the atoms and all of the bonds.
Name the monomer.

name ..................................................................................................................
[2]
(iii) State the empirical formula of:
the monomer ......................................................................................................
the polymer ........................................................................................................
[2]

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(c) Complex carbohydrates are natural condensation polymers. They can be

broken down into colourless monomers which can then be separated and
identified.
X is a complex carbohydrate.
Starting with a sample of X, describe how to produce, separate, detect and
identify the monomers which make it up.
Your answer should include:
● the name of the process used to break down X into its monomers
● two types of substance that can be used to break down X
● the name of the process used to separate the monomers
● the method used to detect the monomers after they have been separated
● the method used to identify the monomers after they have been separated
and detected.
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
............................................................................................................................
....................................................................................................................... [6]
(d) Synthetic polyamides are condensation polymers.
(i) Name a synthetic polyamide.
....................................................................................................................... [1]
(ii) Synthetic polyamides can be made by reacting carboxylic acids with
amines.
Name the other substance that is produced in this reaction.
....................................................................................................................... [1]

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33) May 2020 [41] Q (3_c, d)

(c) Concentrated sulfuric acid is a dehydrating agent which can chemically
remove water from substances.
Both hydrated copper(II) sulfate crystals and sucrose (a sugar), C12H22O11,
can be completely dehydrated by concentrated sulfuric acid.
Name the solid product formed in each case.
hydrated copper(II) sulfate crystals ....................................................................
sucrose ..............................................................................................................
[2]
(d) When propan-1-ol is heated with concentrated sulfuric acid as a catalyst
an unsaturated hydrocarbon of relative molecular mass 42 is formed and one
other product.
(i) What is meant by the term unsaturated ?
....................................................................................................................... [1]
(ii) Write the chemical equation for this reaction.
....................................................................................................................... [2]
(iii) Name the unsaturated hydrocarbon formed.
....................................................................................................................... [1]
34) May 2020 [41] Q (5_a, b, d, e, f)
5 Ethanol is manufactured by two different processes.
(a) For each process, name the organic reactant and state the type of
reaction.
organic reactant ................................... type of reaction ....................................
organic reactant ................................... type of reaction ....................................
[4]
(b) Alcohols can be oxidised to form carboxylic acids.
Name a suitable oxidising agent for this reaction.
............................................................................................................................

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(d) The table shows some information about aldehydes.

(i) Complete the table.

[2]
(ii) Deduce the general formula of aldehydes.
....................................................................................................................... [1]
(e) The structural formula of ethanal is shown.

The C=O group in aldehydes is at the end of the carbon chain.

This is a reactive part of the molecule.
(i) What is the name given to the reactive part of any organic molecule?
....................................................................................................................... [1]
(f) Propanone belongs to a homologous series called ketones. Ketones have
the same C=O group as aldehydes but the C=O group is not at the end of the
carbon chain. Propanone has the same molecular formula as propanal,
C3H6O.
(i) What term is used to describe molecules with different structures but with
the same molecular formula?
....................................................................................................................... [1]
(ii) Suggest the structure of propanone, C3H6O. Show all of the atoms and all
of the bonds.

[2]

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35) May 2020 [42] Q (6)

6 (a) Propane reacts with chlorine in a photochemical reaction as shown.
C3H8 + Cl2 
→ C3H7Cl + HCl
(i) What type of reaction is this?
....................................................................................................................... [1]
(ii) What condition is needed for this photochemical reaction to occur?
....................................................................................................................... [1]
(iii) Draw two structural isomers of compounds with the formula C3H7Cl.
Show all of the atoms and all of the bonds.

[2]
(b) Propene reacts with chlorine in an addition reaction as shown.
C3H6 + Cl2 
→ C3H6Cl2
(i) State why this is an addition reaction.
....................................................................................................................... [1]
(c) There are three functional groups in compound A.

(i) Name the homologous series of compounds that contains the following
structures.
C=C ....................................................................................................................
–OH ....................................................................................................................
–COOH ..............................................................................................................
[3]

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(ii) What would you observe when compound A is added to:

aqueous bromine ...............................................................................................
aqueous sodium carbonate? ..............................................................................
[2]
(d) Compound A can be used as a single monomer to produce two different
polymers.
(i) Draw one repeat unit of the addition polymer formed from compound A.
[2]

(ii) What type of condensation polymer is formed from compound A?

....................................................................................................................... [1]
36) May 2020 [43] Q (1)
1 (a) The structures of five organic compounds, A, B, C, D and E, are shown.
Answer the questions that follow.
Each letter may be used once, more than once or not at all.

(i) Give the letter of the compound that is propan-1-ol.

....................................................................................................................... [1]
(ii) Give the letter of the compound that has the empirical formula CH2.
....................................................................................................................... [1]
(iii) Give the letter of one compound that reacts with bromine in an addition
reaction.
....................................................................................................................... [1]

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(iv) Give the letter of one compound that reacts with chlorine to form the
compound shown.

....................................................................................................................... [1]
(v) Give the letters of two compounds that can react with each other to form
an ester.
........................................................... and …………………………………….. [1]
(vi) Give the letter of the compound that is in the same homologous series as
hex‑1‑ene.
....................................................................................................................... [1]
(vii) Give the letter of one compound that is an acid.
....................................................................................................................... [1]
(viii) Draw a structural isomer of compound D.
Show all of the atoms and all of the bonds.

[1]
37) May 2020 [43] Q (8)
8 (a) Part of the synthetic polymer, nylon, is shown in the diagram.

(i) Circle one amide linkage on the diagram. [1]

(ii) Complete the structures of the two monomers that react to form nylon.

[2]

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(iii) Name the other product formed when nylon is produced.

....................................................................................................................... [1]
(b) Items made from nylon are often disposed of by burying them in the
ground. This is called landfill.
Why is the disposal of nylon using landfill a problem?
............................................................................................................................
....................................................................................................................... [1]
(c) Give the name of a natural polymer.
....................................................................................................................... [1]
38) Nov 2020 [41] Q (6)
6 (a) Ethane, propane and butane are members of the same homologous
series.
(i) Name this homologous series.
....................................................................................................................... [1]
(ii) State two ways members of the same homologous series are similar.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
23
(b) One mole of ethane, C2H6, contains 6.02 × 10 molecules.
Calculate how many molecules are in 15 g of ethane.

number of ethane molecules = .............................. [1]

(c) Propane reacts with chlorine.
(i) Write the formula of the product which does not contain carbon.
....................................................................................................................... [1]
(ii) Draw the structure of an organic product formed. Show all of the atoms
and all of the bonds.

[1]

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(iii) State the name of this type of reaction.

....................................................................................................................... [1]
(d) (i) Aqueous bromine was added to a sample of ethene.
Give the colour change seen.
from ................................................. to ......................................................... [2]
(ii) Explain, in terms of bonding, why there is no colour change when aqueous
bromine is added to ethane.
............................................................................................................................
....................................................................................................................... [1]
(e) There are two structural isomers with the formula C4H10.
(i) Draw the structures of both of these isomers, showing all of the atoms and
all of the bonds.

[2]
(ii) Butane is formed when longer chain hydrocarbons are cracked.
Complete the chemical equation to show the other product when butane is
formed by cracking.
C6H14 
→ C4H10 + ................................
[1]
39) Nov 2020 [41] Q (7)
7 (a) Ethanol can be manufactured by two different methods.
Method 1: fermentation of a sugar, C6H12O6
C6H12O6 
→ 2C2H5OH + 2CO2
Method 2: reaction of ethene with steam
C2H4 + H2O 
→ C2H5OH
(i) Give one advantage of using fermentation compared with Method 2.
............................................................................................................................
....................................................................................................................... [1]

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(ii) Give one disadvantage of using fermentation compared with Method 2.

............................................................................................................................
....................................................................................................................... [1]
(b) Ethanol reacts with acidified potassium manganate(VII) to form water and
a product that turns litmus red.
(i) State the name of the product that turns the litmus red.
....................................................................................................................... [1]
(ii) State the type of reaction that ethanol undergoes when it reacts with
acidified potassium manganate(VII).
....................................................................................................................... [1]
(c) Ethanol reacts with methanoic acid to form an ester.
(i) Name the ester formed in this reaction.
....................................................................................................................... [1]
(ii) Draw the structure of the ester formed.
Show all of the atoms and all of the bonds.

[1]
40) Nov 2020 [42] Q (4)
4 Alkenes and alkanes are homologous series of compounds containing
carbon and hydrogen atoms.
(a) State the name of the type of compound made from carbon and hydrogen
atoms only.
....................................................................................................................... [1]
(b) Alkenes take part in addition reactions.
(i) Describe what is meant by the term addition reaction.
....................................................................................................................... [1]
(ii) Draw the structure of the product made in the addition reaction between
propene and bromine. Show all of the atoms and all of the bonds.

[2]

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(iii) Describe the colour change seen when propene is added to aqueous
bromine.
from .................................................. to ........................................................ [2]
(iv) Draw the structures of molecules of two different alkenes which both
undergo an addition reaction with steam to form butan-2-ol. Show all of the
atoms and all of the bonds.

[2]
(c) Propane undergoes a substitution reaction with chlorine.
Write the chemical equation for the reaction between one molecule of
propane and one molecule of chlorine.
....................................................................................................................... [2]
41) Nov 2020 [42] Q (5_a, i, ii, c, d)
5 This question is about alcohols, carboxylic acids and esters.
(a) Ethanol will react with hot aqueous potassium manganate(VII) to form
ethanoic acid.
(i) State the other condition needed for this reaction to take place.
....................................................................................................................... [1]
(ii) State the type of chemical change that happens to the ethanol during this
reaction.
....................................................................................................................... [1]
(c) Ethanoic acid will react with an alcohol to form the ester shown.

(i) Name the other product formed when ethanoic acid reacts with an alcohol
to make this ester.
....................................................................................................................... [1]

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(ii) Give one condition needed when ethanoic acid reacts with the alcohol to
make this ester.
....................................................................................................................... [1]
(iii) Draw the structure of the alcohol which was added to ethanoic acid to
make this ester.
Show all of the atoms and all of the bonds.

[2]
(d) Polyesters can be manufactured from carboxylic acids and alcohols.
Hexanedioic acid has the structure: HOOC–CH2–CH2–CH2–CH2–COOH.
This structure can be simplified as shown.

Ethanediol has the structure: HO–CH2–CH2–OH.

This structure can be simplified as shown.

The functional groups are found at the end of each molecule.

(i) State what is meant by the term functional group.
....................................................................................................................... [1]
(ii) Determine the empirical formula of hexanedioic acid.
....................................................................................................................... [1]
(iii) Calculate the percentage by mass of oxygen present in ethanediol.
Give your answer to the nearest whole number.

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

354 13 – Organic Chemistry Mostafa Barakat (0100 165 44 62)

Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(iv) Complete the diagram to show a section of polyester manufactured from

hexanedioic acid and ethanediol. Include all of the atoms and all of the bonds
in the linkages.

[2]
(v) State the name of a polyester.
....................................................................................................................... [1]
42) Nov 2020 [43] Q (6)
6 (a) A carboxylic acid and an ester are structural isomers.
(i) State the meaning of the term structural isomers.
............................................................................................................................
............................................................................................................................
....................................................................................................................... [2]
(ii) Draw the structures of the carboxylic acid and the ester which both contain
two carbon atoms.
Show all of the atoms and all of the bonds.
Name the carboxylic acid and the ester.

[4]

355 13 – Organic Chemistry Mostafa Barakat (0100 165 44 62)

Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(b) Part of a polyester chain is shown. This polyester is made from one
monomer.

(i) On the diagram draw a ring around one unit of the polymer that is
repeated. [1]
(ii) Name the type of polymerisation that produces polyesters.
....................................................................................................................... [1]
(iii) Complete the diagram to show the structure of the monomer used to
produce this polyester.
Show all of the atoms and all of the bonds in the functional groups.

[2]
(c) A polyamide is made from the two monomers shown.

Complete the diagram to show a section of the polyamide made from the two
monomers.
Show all of the atoms and all of the bonds in the linkages.

[2]
(d) Naturally occurring polyamides are constituents of food.
(i) State the name given to naturally occurring polyamides.
....................................................................................................................... [1]
(ii) Name the monomers which form naturally occurring polyamides.
....................................................................................................................... [1]

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43) May 2021 [41] Q (7_c, d)

(c) Compounds X and Y have the same general formula.
X and Y are both carboxylic acids.
Compound X has the molecular formula C2H4O2.
Compound Y has the molecular formula C4H8O2.
(i) Deduce the general formula of compounds X and Y.
....................................................................................................................... [1]
(ii) Draw the structure of compound Y. Show all of the atoms and all of the
bonds.
Name compound Y.

name ..................................................................................................................
[3]
(iii) Give the name used to describe a ‘family’ of similar compounds with the
same general formula, similar chemical properties and the same functional
group.
....................................................................................................................... [1]
(d) Propene is an unsaturated hydrocarbon. The formula of propene is shown.
CH3CH=CH2
(i) State the colour change observed when propene is added to aqueous
bromine.
from ................................................ to .......................................................... [1]
(ii) Propene can be produced by cracking long chain alkanes.
Pentadecane, C15H32, is cracked to produce an alkane and propene in a 1 : 2
molar ratio.
Complete the chemical equation for this reaction.
C15H32 
→ ................................. + .................................
[2]
(iii) Propene can be converted into poly(propene).
Name the type of polymerisation that occurs when propene is converted into
poly(propene).
....................................................................................................................... [1]

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(iv) Complete the diagram to show a section of poly(propene).

[2]
44) May 2021 [42] Q (2_f)
(f) Members of one homologous series only react with chlorine in the
presence of sunlight.
(i) Name a member of this homologous series.
....................................................................................................................... [1]
(ii) Name two products that form when the compound in (i) reacts with
chlorine.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
45) May 2021 [42] Q (6)
6 Molecules A and B can form condensation polymers.

(a) Each molecule has two identical functional groups.

(i) Name the functional group in B.
....................................................................................................................... [1]
(ii) Draw the part of the structure of the synthetic polymer that would form
when two molecules of A and two molecules of B combine. Show all of the
bonds in the linkages.

[3]

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(iii) Name the other product formed when molecules of A and B undergo
polymerisation.
....................................................................................................................... [1]
(c) Ethanol can be made from the simple sugar glucose, C6H12O6.
(i) State the name of this process.
....................................................................................................................... [1]
(ii) Complete the chemical equation for this reaction.
C6H12O6 
→
[2]
46) May 2021 [43] Q (1_a, c, f)
1 Give the name of the process that is used:
(a) to produce large molecules from monomers
....................................................................................................................... [1]
(c) to make ethanol from glucose
....................................................................................................................... [1]
(f) to separate the products of hydrolysis of long chain carbohydrates
....................................................................................................................... [1]
47) May 2021 [43] Q (7_c, d)
(c) Compounds T and V have the same molecular formula, C3H6O2.
● Compound T is an ester.
● Compound V contains a –COOH functional group.
(i) State the name given to compounds with the same molecular formula but
different
structures.
....................................................................................................................... [1]
(ii) Name the homologous series that V is a member of.
....................................................................................................................... [1]
(iii) Draw a structure of compound T. Show all of the atoms and all of the
bonds.
Name compound T.

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

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(iv) Draw the structure of compound V. Show all of the atoms and all of the
bonds.
Name compound V.

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

(d) Ethanol can be produced from long chain alkanes such as decane, C10H22,
in a two-step process.

For each of the two steps:

● name the type of chemical reaction that occurs
● write a chemical equation.
step 1: decane to ethene
type of reaction ..................................................................................................
chemical equation ..............................................................................................
step 2: ethene to ethanol
type of reaction ..................................................................................................
chemical equation ..............................................................................................
[4]

360 13 – Organic Chemistry Mostafa Barakat (0100 165 44 62)

Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

48) Nov 2021 [41] Q (5)

5 Alkenes and carboxylic acids are both families of similar compounds with
similar chemical properties.
Alkenes and carboxylic acids have different reactions.
(a) State the term used for a ‘family’ of similar compounds.
....................................................................................................................... [1]
(b) State the general formula of alkenes.
....................................................................................................................... [1]
(c) The structure of but-2-ene is shown.

(i) But-2-ene reacts with aqueous bromine in an addition reaction.

Describe the colour change seen when but-2-ene is added to aqueous
bromine.
from ................................................... to ....................................................... [1]
(ii) State what is meant by the term addition reaction.
....................................................................................................................... [1]
(iii) Write the chemical equation for the reaction between but-2-ene and
bromine.
....................................................................................................................... [2]
(iv) But-2-ene forms a polymer.
Suggest the name of the polymer formed from but-2-ene.
....................................................................................................................... [1]
(v) Name and draw a structural isomer of but-2-ene.
Show all of the atoms and all of the bonds.
name ..................................................................................................................

structure
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(d) Butanoic acid, CH3CH2CH2COOH, is a carboxylic acid.

(i) Deduce the empirical formula of butanoic acid.
....................................................................................................................... [1]
(ii) Complete the chemical equation for the reaction of butanoic acid and
sodium carbonate, Na2CO3.
2CH3CH2CH2COOH + Na2CO3 
→ ........................ + ............... + ...............
[2]
(iii) Butanoic acid reacts with methanol to form an organic compound and
water.
● Name the organic compound formed.
....................................................................................................................... [1]
● Draw the structure of the organic compound formed.
Show all of the atoms and all of the bonds.

[2]
49) Nov 2021 [42] Q (6)
6 Ethanol, C2H5OH, belongs to the homologous series called alcohols.
(a) Write the general formula of alcohols.
....................................................................................................................... [1]
(b) Explain why ethanol cannot be described as a hydrocarbon.
....................................................................................................................... [1]
(c) Ethanol can be manufactured from different substances by reaction with
steam or by fermentation.
(i) Give the formula of the substance which reacts with steam to form ethanol.
....................................................................................................................... [1]
(ii) Name a substance which will undergo fermentation to form ethanol.
....................................................................................................................... [1]
(d) Ethanol is a fuel.
Write the chemical equation for the complete combustion of ethanol.
....................................................................................................................... [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(e) Ethane-1,2-diol has two alcohol functional groups.

One molecule of ethane-1,2-diol will react with two molecules of ethanoic acid
to form molecule X.
X has two ester functional groups and a molecular formula of C6H10O4.
(i) State the empirical formula of X.
....................................................................................................................... [1]
(ii) Draw the structure of X.
Show all of the atoms and all of the bonds.

[2]
(iii) Name the other substance formed in this reaction.
....................................................................................................................... [1]
(f) Each alcohol functional group in ethane-1,2-diol reacts with acidified
potassium manganate(VII) to form a different organic compound, Y.
(i) Name the functional groups formed in Y.
....................................................................................................................... [1]
(ii) Draw the structure of Y.
Show all of the atoms and all of the bonds.

[1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

50) Nov 2021 [43] Q (7)

7 (a) Ethanol is a member of the homologous series of alcohols.
Give two characteristics of members of a homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(b) Ethanol can be manufactured from ethene.
Ethene can be made from long chain hydrocarbons such as decane, C10H22.
Ethene is then converted into ethanol.
(i) Name the process used to obtain ethene from long chain hydrocarbons
such as decane, C10H22.
....................................................................................................................... [1]
(ii) Complete the chemical equation to show the formation of ethene from
decane, C10H22.
C10H22 
→ C4H8 + ................... + ...................
[2]
(iii) Write the chemical equation for the conversion of ethene into ethanol.
....................................................................................................................... [1]
(iv) Name the type of reaction occurring when ethene is converted into
ethanol.
....................................................................................................................... [1]
(v) Give one condition for the reaction in which ethene is converted into
ethanol.
....................................................................................................................... [1]
(c) Ethanol can also be produced by fermentation of carbohydrates such as
glucose.
Give two advantages of manufacturing ethanol by fermentation compared to
manufacturing ethanol from ethene.
1 .........................................................................................................................
2 .........................................................................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(d) (i) Under certain conditions ethene can react with chlorine to produce
chloroethene.
The structure of chloroethene is shown.

The equation for the chemical reaction is shown.

C2H4 + Cl2 
→ C2H3Cl + HCl
State the type of chemical reaction between ethene and chlorine that this
equation shows.
....................................................................................................................... [1]
(ii) Chloroethene monomers can be converted into a polymer called
poly(chloroethene).
State the type of polymerisation that produces poly(chloroethene) from
chloroethene.
....................................................................................................................... [1]
(iii) Draw a section of the poly(chloroethene) molecule made from two
monomer molecules.

[2]
(e) The structure of part of a polymer is shown.

This polymer is made from one type of monomer only.

Complete the diagram to show the structure of the monomer used to produce
this polymer.
Show all of the atoms and all of the bonds in the functional groups.

[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

51) May 2022 [41] Q (1_c, d)

1 A list of substances is shown.

Answer the questions using the list of substances.

Each substance may be used once, more than once or not at all.
State which of the substances:
(c) are two products of fermentation
........................................................ and ....................................................... [2]
(d) is used as a fuel
....................................................................................................................... [1]
52) May 2022 [41] Q (5_e, f, g)
(e) Ethanoic acid is a member of the homologous series of carboxylic acids.
State the general formula of this homologous series.
....................................................................................................................... [1]
(f) Draw the structure of the carboxylic acid containing three carbon atoms.
Show all of the atoms and all of the bonds.

[2]
(g) When carboxylic acids react with alcohols, esters are produced.
The formula of ester X is CH3CH2CH2COOCH3.
(i) Name ester X.
....................................................................................................................... [1]

(ii) Give the name of the carboxylic acid and the alcohol that react together to
produce ester X.
carboxylic acid ...................................................................................................
alcohol ................................................................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

53) May 2022 [42] Q (5)

5 The reaction scheme shows five organic reactions, numbered 1 to 5.

(a) Name reaction 1.

....................................................................................................................... [1]
(b) Name reaction 2 and write the chemical equation for this reaction.
name ..................................................................................................................
equation .............................................................................................................
[3]
(c) Reaction 3 forms ethanol from alkene A.
(i) Identify alkene A.
....................................................................................................................... [1]
(ii) State the type of reaction that occurs during reaction 3.
....................................................................................................................... [1]
(iii) State the reagents and conditions needed for reaction 3.
............................................................................................................................
....................................................................................................................... [2]
(d) Alkene A is converted into alkane B in reaction 4.
(i) State the reagent and conditions for reaction 4.
............................................................................................................................
....................................................................................................................... [3]
(ii) State the general formula of alkanes.
....................................................................................................................... [1]
(e) Ethanol is oxidised in reaction 5 by heating it with dilute sulfuric acid and
one other reagent.
(i) Identify the other reagent in reaction 5.
....................................................................................................................... [1]
(ii) Name the homologous series compound C belongs to.
....................................................................................................................... [1]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(iii) Draw the structure of compound C.

Show all of the atoms and all of the bonds.

[1]
54) May 2022 [42] Q (6)
6 This question is about polymers.
(a) Polymer X is a condensation polymer.
Part of the structure of polymer X is shown.

(i) How many molecules of water are produced when this part of polymer X is
formed from its monomers?
....................................................................................................................... [1]
(ii) Complete the structures of the two monomers used to make polymer X.
Show all of the atoms and all of the bonds in the functional groups.

[2]
(iii) What type of condensation polymer is X?
....................................................................................................................... [1]
(b) Part of polymer Y has the structure shown.

State the number of different types of monomer needed to make polymer Y.

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

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(c) Part of polymer Z has the structure shown.

(i) Draw and name the structure of the monomer which forms polymer Z.
Show all of the atoms and all of the bonds.

name ...............................................
[3]
(ii) Name the chemical process used to make the monomer that forms
polymer Z.
....................................................................................................................... [1]
55) May 2022 [43] Q (4_c, d)
(c) Ethanol is a member of the alcohol homologous series.
Members of the same homologous series have the same general formula.
(i) State the general formula of alcohols.
....................................................................................................................... [1]
(ii) State two general characteristics, other than the same general formula, of
all homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(iii) One alcohol containing three carbon atoms is propan-1-ol.

Draw the structure of one other alcohol containing three carbon atoms. Show
all of the atoms and all of the bonds.
Name the alcohol you have drawn.

name ..................................................................................................................
[2]
(d) When alcohols react with carboxylic acids, esters are produced.
(i) The structure of ester X is shown.

Name ester X.
....................................................................................................................... [1]
(ii) Give the name of the alcohol and the carboxylic acid that react together to
produce ester X.
alcohol ................................................................................................................
carboxylic acid ...................................................................................................
[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

56) SPECIMEN PAPER 2023 [41] Q (6)

6 Alkynes and alkenes are homologous series of unsaturated hydrocarbons.
All alkynes contain a C≡C triple bond.
(a) Complete Table 6.1 showing information about the first three alkynes.

[2]
(b) Compounds in the same homologous series have the same general
formula.
(i) Give two other characteristics of members of a homologous series.
1 .........................................................................................................................
2 .........................................................................................................................
[2]
(ii) Deduce the general formula of alkynes.
Use the information from Table 6.1 to help you.
....................................................................................................................... [1]
(iii) Alkynes are unsaturated.
Describe a test for unsaturation.
test .....................................................................................................................
result ..................................................................................................................
[2]
(c) Ethene and but-2-ene are alkenes.
(i) Draw the displayed formula of but-2-ene.

[2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

(ii) Draw a dot-and-cross diagram to show a molecule of ethene, CH2=CH2.

Show outer shell electrons only.

[2]
(d) Ethene can be converted to ethanoic acid by a two-stage process.
In stage one, ethene is converted to ethanol by catalytic addition.
C2H4 + H2O 
→ C2H5OH
(i) Suggest why stage one is called an addition reaction.
....................................................................................................................... [1]
(ii) A catalyst is used in stage one.
State one other condition that must be used.
....................................................................................................................... [1]
(iii) State what must be reacted with ethanol to form ethanoic acid.
....................................................................................................................... [2]

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Cambridge IGCSE Chemistry Classified Paper_4_Topic 13

57) SPECIMEN PAPER 2023 [41] Q (7)

7 Carboxylic acids can be converted into esters.
(a) Propanoic acid and methanol react to form an ester that has the molecular
formula C4H8O2.
(i) Name this ester and draw its displayed formula.
name of ester .....................................................................................................
displayed formula

[2]
(ii) Name another ester with the molecular formula C4H8O2.
....................................................................................................................... [1]
(b) Polyesters are polymers made from dicarboxylic acids.
(i) Name the other type of organic compound used in the formation of
polyesters.
....................................................................................................................... [1]
(ii) Name the type of polymerisation used in the manufacture of polyesters.
....................................................................................................................... [1]

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