Q1.

Which statement is correct about the fractional distillation of crude oil?

A A zeolite catalyst is used.

B Each fraction contains a mixture of hydrocarbons.

C Gaseous fractions are formed by breaking covalent

bonds.
D The fractionating column is hottest at the top.

(Total 1 mark)

Q2.
(a) (i) Name the process used to separate petroleum into fractions.

______________________________________________________________

(ii) Give the molecular formula for an alkane with nine carbon atoms.

______________________________________________________________

______________________________________________________________

(iii) Write an equation for the complete combustion of the alkane C11H24

______________________________________________________________

(iv) Write an equation for the incomplete combustion of C11H24 to produce carbon
and water only.

______________________________________________________________
(4)

(b) Alkenes can be produced by cracking the naphtha fraction obtained from petroleum.

(i) Write an equation for the thermal cracking of one molecule of C10 H22 to give
one molecule of propene and one molecule of an alkane only.

______________________________________________________________

(ii) Draw the structure of the chain isomer of but-1-ene.

(2)

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 (c) The alkanes and the alkenes are examples of homologous series of compounds.
One feature of an homologous series is the gradual change in physical properties
as the relative molecular mass increases. State two other general features of an
homologous series of compounds.

Feature 1 ___________________________________________________________

___________________________________________________________________

Feature 2 ___________________________________________________________

___________________________________________________________________
(2)
(Total 8 marks)

Q3.
The following table shows the boiling points of some straight-chain alkanes.

CH4 C2 H6 C3 H8 C4H10 C5H12

Boiling point / °C −162 −88 −42 −1 36

(a) State a process used to separate an alkane from a mixture of these alkanes.

___________________________________________________________________
(1)

(b) Both C3H8 and C4H10 can be liquefied and used as fuels for camping stoves.

Suggest, with a reason, which of these two fuels is liquefied more easily.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(c) Write an equation for the complete combustion of C4H10

___________________________________________________________________
(1)

(d) Explain why the complete combustion of C4H10 may contribute to environmental
problems.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e) Balance the following equation that shows how butane is used to make the
compound called maleic anhydride.

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 ..........CH3CH2CH2CH3 + .......... O2 ..........C2H2(CO)2O + .......... H2O
(1)

(f) Ethanethiol (C2H5SH), a compound with an unpleasant smell, is added to gas to

enable leaks from gas pipes to be more easily detected.

(i) Write an equation for the combustion of ethanethiol to form carbon dioxide,
water and sulfur dioxide.

______________________________________________________________
(1)

(ii) Identify a compound that is used to react with the sulfur dioxide in the products
of combustion before they enter the atmosphere.

Give one reason why this compound reacts with sulfur dioxide.

Substance ____________________________________________________

Reason _______________________________________________________

______________________________________________________________
(2)

(iii) Ethanethiol and ethanol molecules have similar shapes.

Explain why ethanol has the higher boiling point.

______________________________________________________________

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(g) The following compound X is an isomer of one of the alkanes in the table on above.

(i) Give the IUPAC name of X.

______________________________________________________________
(1)

(ii) X has a boiling point of 9.5 °C.

Explain why the boiling point of X is lower than that of its straight-chain isomer.

______________________________________________________________

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 ______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(iii) The following compound Y is produced when X reacts with chlorine.

Deduce how many other position isomers of Y can be formed.

Write the number of other position isomers in this box.

(1)

(h) Cracking of one molecule of an alkane Z produces one molecule of ethane, one
molecule of propene and two molecules of ethene.

(i) Deduce the molecular formula of Z.

______________________________________________________________
(1)

(ii) State the type of cracking that produces a high proportion of ethene and
propene.
Give the two conditions for this cracking process.

Type of cracking ________________________________________________

Conditions _____________________________________________________

______________________________________________________________
(2)
(Total 17 marks)

Q4.
Pent-1-ene is a member of the alkene homologous series.

(a) Pent-1-ene can be separated from other alkenes.

State the physical property of alkenes that allows them to be separated from a
mixture by fractional distillation.

___________________________________________________________________
(1)

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(b) (i) State the meaning of the term structural isomerism.

______________________________________________________________

______________________________________________________________

______________________________________________________________
(2)

(ii) Name the branched chain isomer of pent-1-ene shown below.

______________________________________________________________
(1)

(iii) Draw the structure of a functional group isomer of pent-1-ene.

(1)

(c) The cracking of one molecule of compound X produces pent-1-ene, ethene and
butane in a 1:2:1 mol ratio.
Deduce the molecular formula of X and state a use for the ethene formed.

Molecular formula of X ________________________________________________

___________________________________________________________________

Use of ethene _______________________________________________________

(2)
(Total 7 marks)

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Mark schemes

Q1.
B
[1]

Q2.
(a) (i) fractional distillation or fractionation
1

(ii) C9H20 only

1

(iii) C11H24 + 17O2 → 11CO2 + 12H2O

1

(iv) C11H24 + 6O2 → 11C + 12H2O

1

(b) (i) C10H22 → C3H6 + C7H16

1

(ii) correctly drawn structure of methylpropene

(insist on clearly drawn C-C and C=C bonds)
1

(c) Any two from

o chemically similar or chemically the same or react in

the same way

o same functional group

o same general formula

o differ by CH2
(penalise same molecular formula or same empirical
formula)
2
[8]

Q3.
(a) Fractional distillation / fractionation / GLC / gas liquid chromatography
1

(b) C4H10
Need C4H10 and the reason for the mark

Because it has a higher bp / has stronger IMF / larger molecule / longer chain /
larger surface (area)
1

(c) C4H10 + 6½ O2 4CO2 + 5H2O

Accept multiples

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 Ignore state symbols
1

(d) CO2 or H2O evolved is a greenhouse gas / CO2 or H2O evolved contribute to
global warming / the products are greenhouse gases
Ignore climate change
1

(e) CH3CH2CH2CH3 + 3.5O2 C2H2(CO)2O + 4H2O

Accept multiples
Allow with or without a number 1 before the organic
molecules
1

(f) (i) C2H5SH + 4.5O2 2CO2 + 3H2O + SO2

Accept multiples
1

(ii) Calcium oxide / calcium carbonate

Allow any base or alkali
Allow correct formulae
1

Neutralises the SO2 / acid base reaction / it is a base

Can only score M2 if base or alkali used in M1
Allow M2 if blank in M1
1

(iii) Ethanol contains hydrogen bonding

Breaking covalent bonds CE = 0 / 2

Which is stronger than IMF (VDW / dipole-dipole forces) in ethanethiol /

(H bonding) is the strongest IMF
Only award M2 if M1 given, but allow IMF in ethanol are
stronger than in ethanethiol for maximum 1 mark
1

(g) (i) (2,2-)dimethylpropane

Ignore punctuation
1

(ii) Because molecule is smaller / less polarisable / has less surface (area) /
is more spherical / molecules can’t get as close to one another (to feel
the vdW forces)
Allow converse answers referring to straight chain isomers
CE = 0 / 2 if breaking bonds
1

vdW intermolecular forces or vdW force between molecules are weaker

or fewer
Need vdW rather than just IMF
1

(iii) 1 or one
1

(h) (i) C9H20

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 H20C9
1

(ii) Thermal (cracking)

If not thermal cracking CE = 0 / 2
1

High pressure AND high temperature

If blank mark on
Allow high P and T
1

OR

Pressure of ≥ 10 atm, ≥ 1 MPa ≥ 1000 kPa

AND temp of 400 °C ≤ T ≤ 1000 °C or 650 K ≤ T≤ 1300 K

Do not allow high heat
If no units for T, then range must be 650 − 1000
1
[17]

Q4.
(a) (Different) boiling points
Ignore mp’s, references to imf, different volatilities
1

(b) (i) Compound which have the same molecular formula

Accept same no and type of atom for M1
But If same (chemical) formula M1 = 0 but allow M2
If empirical formula CE = 0/2
1

but different structures/different structural

formulae/different displayed formulae
M2 dependent on M1
1

(ii) 3-methylbut-1-ene
only
ignore commas and hyphens
1

(iii)

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 Allow any correct structure with a cyclic alkane
1
Do not allow

i.e with an H missing on one C

(c) C13H28
only
1

Making plastics/used to make polymers or polythene/used

to make antifreeze/make ethanol/ripening fruit/any named
additional polymer
not used as a plastic/polymer/antifreeze
not just ‘polymers’ – we need to see that they are being
made
1
[6]

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