1.

What is the correct name for the compound below?

E-2,3-dibromopent-2-ene

E-2,3-dibromopent-3-ene

Z-2,3-dibromopent-3-ene

Z-2,3-dibromopent-2-ene
(Total 1 mark)

2.

The equations below show some of the processes that occur when methane and chlorine react.
A

Cl2(g) 2Cl(g)

Cl(g) + CH4(g) CH3(g) + HCl(g)

CH3(g) + CH3(g) C2H6(g)

Cl2(g) + CH4(g) CH3Cl(g) + HCl(g)

(a)

Which equation shows a propagation step?

A
B
C
D
(1)

(b)

Which equation shows an initiation step?

A
B
C
D
(1)

(c)

Which equation shows a termination step?

A
B
C
D
(1)
(Total 3 marks)

(b)

Study the reaction scheme below and then answer the questions that follow.

(i)

Name the reagent and catalyst needed for Reaction 1.

Reagent.............................................................................................................
Catalyst.............................................................................................................
(2)

(ii)

Give the name and displayed formula of compound X.

Name.................................................................................................................
Displayed formula

(2)

(iii)

Describe what colour change you would see during Reaction 4 if a small amount of acidified
KMnO4(aq) was shaken with ethene.
From................................................. to..............................................................
(1)

(c)

(i)

Use displayed formulae to show the mechanism for Reaction 3.

(3)

(ii)

Explain why the alkene, propene, could form two products when it reacts with hydrogen
bromide in a similar way.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(d)

The formula of the alkene phenylethene, often called styrene, is shown below. It can be used to make
the polymer poly(styrene).

Draw a section of the poly(styrene) polymer chain formed from two monomer units.

(2)

5.

Consider the following compounds, P, Q, R and S.

CH3CH2CH3

Compound P

Compound Q

CH3CH2CH2CH2Br

Compound R
9.

(a)

Compound S

Propene, C3H6, reacts with hydrogen bromide, HBr, in an electrophilic addition reaction.
2-bromopropane is formed as the major product.
H3CCH==CH2 + HBr H3CCH(Br)CH3
(i)

Complete the mechanism for the reaction, using curly arrows where appropriate. Show clearly
the structure of the intermediate carbocation formed.

(3)

(ii)

Draw the structure of the alternative carbocation that can be formed in the reaction between
propene and hydrogen bromide.
(1)

32.

Which of the following mixtures could not form when octane, C8H18, is cracked?

propane + pentene

butane + butene

pentane + propene

heptane + ethene
(Total 1 mark)

33.

This question is about the organic compounds with skeletal formulae as shown:

(a)

Which compound is 2-methylpropane?

A
B
C
D
(1)

(b)

Which compound has the molecular formula C5H12?

A
B
C
D
(1)

(c)

(d)

Which compounds are isomers?

A

compound A and compound C

compound B and compound C

compound B and compound D

compound C and compound D

Which compound reacts with acidified potassium manganate(VII) to form a diol?

A
B
C
D

34.

The structural formula of 5-chloro-2,2-dimethylhexane is

(Total 1 mark)

35.

This question is about hexane, C6H14, and hex-1-ene, C6H12.

(a)

What test would you use to distinguish between hexane and hex-1-ene? Give the results of the test for
each substance.
Test: ............................................................................................................................
.....................................................................................................................................
Result with hexane: ....................................................................................................
.....................................................................................................................................

Result with hex-1-ene: ................................................................................................

......................................................................................................................................
(2)

(b)

Hex-1-ene has a number of isomers, including two stereoisomers of hex-2-ene.

(i)

Complete the formula to show the structure of E-hex-2-ene.

(1)

(ii)

Explain why stereoisomerism can occur in alkenes, and why hex-2-ene has stereoisomers but
hex-1-ene does not.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(d)

Hex-1-ene can be converted to hexane in the following reaction.

C6H12(l) + H2(g) C6H14(l)
(i)

What catalyst is used in this reaction?

...........................................................................................................................
(1)

(ii)

The enthalpy change of this reaction Hreaction can be calculated from the following enthalpy
changes of combustion.

Substance

Enthalpy change of combustion

/kJ mol1

Hex-1-ene, C6H12

4003

Hydrogen, H2

286

Hexane, C6H14

4163

Complete the Hess cycle by adding labelled arrows. Use your cycle to calculate the enthalpy
change Hreaction.

(3)

(iii)

The enthalpy change for the reaction of some other alkenes with hydrogen is shown below.

Reaction

Standard enthalpy change

/ kJ mol1

C3H6 + H2 C3H8

4003

C4H8 + H2 C4H10

286

C5H10 + H2 C5H12

4163

Explain why the values are so similar.

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)
(Total 17 marks)

36.

Chloroethane, C2H5Cl, can be made from either ethane or ethene.

(a)

(i)

What reagent and condition would be used to make chloroethane from ethane?
Reagent................................................................................................
Condition...............................................................................................
(2)

(ii)

State the type of reaction and mechanism by which this reaction occurs.
...........................................................................................................................

(2)

(b)

(i)

What reagent would be used to make chloroethane from ethene?

...........................................................................................................................
(1)

(ii)

Show, in full, the mechanism for this reaction in which ethene is converted to chloroethane.
(3)

(c)

Which method of making chloroethane has

a higher atom economy? ................................................................................

a higher percentage yield? ..............................................................................

Explain your answers.

Higher atom economy ................................................................................................
.....................................................................................................................................
Higher percentage yield ..............................................................................................
.....................................................................................................................................
(3)

(d)

The compound chloroethene, CH2==CHCl, forms an addition polymer.

(i)

Draw a diagram, using dots or crosses, to show the arrangement of electrons in chloroethene.
Only the outer shell electrons need be shown.
(2)

(ii)

Chloroethene can form an addition polymer. Write the displayed formula of poly(chloroethene)
showing two repeat units.
(1)

(iii)

Poly(chloroethene) is commonly known as PVC. Almost a quarter of the PVC which is

manufactured is used to make water pipes, which were formerly made of metal.
Give TWO factors which have to be considered when deciding which material, PVC or metal,
contributes to more sustainable uses of resources in the long term.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
(2)
(Total 16 marks)

37.

Which of the following has the highest boiling temperature?

A

Pentane, CH3CH2CH2CH2CH3

Hexane, CH3CH2CH2CH2CH2CH3

2-methylbutane, CH3CH(CH3)CH2CH3

2-methylpentane, CH3CH(CH3)CH2CH2CH3
(Total 1 mark)

54.

This question is about hydrocarbons.

(a)

Liquefied petroleum gas (LPG) is a fuel sold as an alternative to petrol. It is a mixture of liquefied C3
and C4 alkanes.
(i)

Suggest a reason why the alkanes are liquefied.

...........................................................................................................................
...........................................................................................................................
(1)

(ii)

There are two C4 alkanes.

Draw skeletal formulae of each of the C4 alkanes in the spaces provided.
Name each alkane.
First skeletal formula

Second skeletal formula

Name: ..

Name: .
(4)

(iii)

Complete the following sentence.

Compounds with the same molecular formula but different structural formula are called
........................................
(1)

(b)

Propane, C3H8, reacts with chlorine, Cl2, in a substitution reaction.

C3H8 + Cl2 C3H7Cl + HCl
The mechanism for this reaction is described in three stages.
(i)

Give the initiation step for this reaction and state the condition necessary for this step to occur.
Initiation step

Condition.........................................................................................................
(2)

(ii)

Give the TWO propagation steps for this reaction.

(2)

(iii)

Give a possible termination step for this reaction.

(1)

(c)

Myrcene, C10H16, is a naturally occurring compound which is used in perfumes.

(i)

Name the functional group in myrcene.

...............................................................................................................
(1)

(ii)

What colour change would you observe when bromine, dissolved in an organic solvent, is
added to myrcene?
From..................................................to............................................................
(1)

(iii)

Classify the type and mechanism of the reaction that occurs when myrcene reacts with bromine,
Br2.

...........................................................................................................................
...........................................................................................................................
(2)

(iv)

In an experiment, 1.36 g of myrcene (molar mass: 136 g mol1) was found to react with 0.72
dm3 of hydrogen, H2, in the presence of a nickel catalyst.
Use this information to draw the structural formula of the product of the reaction between
myrcene and hydrogen.
[Assume the molar volume of H2 under the conditions of the experiment is 24 dm3mol1.]
Calculation

Hence structural formula of the product

(d)

Myrcene is one of a group of compounds related to 2-methylbut-2-ene shown below.

2-methylbut-2-ene undergoes addition polymerization in a similar way to ethene.

Draw the structural formula of the repeat unit of the polymer formed.
(2)

60.

61.

Which of these compounds is a secondary halogenoalkane?

A

CH3CH(OH)CH3

CH3CCl(CH3)CH3

CH3CHClCH3

CH3CH2CH2Cl

Which of these isomers has the highest boiling temperature?

(Total 1 mark)

62.

When 2-chloro-2-methylpropane is heated in a mixture of water and ethanol at 65 C, two types of reaction
occur. A mixture of two organic products, 2-methylpropan-2-ol and 2-methylpropene, is formed.

(a)

(i)

Name the two reaction types that are taking place.

Reaction 1........................................................................................................
Reaction 2........................................................................................................
(2)

(ii)

Explain how the two products form, by describing the role of the water in each case.
Reaction 1.........................................................................................................
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
Reaction 2.........................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(4)

(b)

A proposed mechanism for Reaction 1 involved the formation of the carbocation,

(i)

What type of bond breaking must have occurred during the carbocation formation?
...........................................................................................................................
(1)

(ii)

Suggest why 1-chlorobutane reacts with water via a different mechanism.

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(c)

Another halogenoalkane, 2-chlorobutane, behaves in a similar way to 2-chloro-2-methylpropane but in

Reaction 2 can form three different alkenes.
Suggest how three different alkenes can form and give their displayed formulae.
.....................................................................................................................................
.....................................................................................................................................

.....................................................................................................................................
(4)

(d)

Suggest why 2-fluoro-2-methylpropane would react more slowly than 2-chloro-2-methylpropane in

Reaction 1.
What reagent could you use instead of water to increase the rate of this reaction involving 2-fluoro-2methylpropane? Explain why the reagent would have this effect.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)
(Total 16 marks)

67.

How many isomers are there of C5H12?

A

Two

Three

Four

Five
(Total 1 mark)

68.

In a molecule of ethene, C2H4, how many (pi) bonds are present?

A

One

Two

Three

Four
(Total 1 mark)

69.

The mechanism of the reaction represented by the equation

C2H4 + Br2 CH2BrCH2Br
is an example of
A

Free radical substitution

Free radical addition

Electrophilic substitution

Electrophilic addition
(Total 1 mark)

70.

What is the systematic name for the following compound?

Z-4-methylhex-2-ene

E-2-ethylpent-3-ene

Z-4-ethylpent-2-ene

E-4-methylhex-2-ene
(Total 1 mark)

71.

Propene reacts with hydrogen chloride gas to give mainly

A

1-chloropropane (CH3CH2CH2Cl)

2-chloropropane (CH3CHClCH3)

3-chloroprop-1-ene (CH2==CHCH2Cl)

1,2-dichloropropane (CH3CHClCH2Cl)
(Total 1 mark)

72.

(a)

State the general formula of the alkanes, using the letter n to denote the number of carbon atoms in
each molecule.
(1)

(b)

Alkanes are used as fuels. In the petrochemical industry, useful hydrocarbons are often produced from
longer chain molecules.
Name the type of reaction shown below.
(i)

Type of reaction .......................................

(1)

(ii)

Type of reaction .......................................

(1)

(c)

By what type of formula are the organic molecules in (b) represented?

.....................................................................................................................................
(1)

(d)

Another reaction carried out in industry can be represented as shown below.

(i)

Give the molecular formula of compound 2.

...............................................................................................................
(1)

(ii)

Give the name of compound 2.

...............................................................................................................
(1)

(e)

An equation for the reaction between methane and chlorine is:

CH4 + Cl2 CH3Cl + HCl

The reaction occurs in the presence of ultraviolet (UV) light via a free-radical chain mechanism.
The initiation step is Cl2 2Cl
The next step could be
EITHER

CH4 + Cl CH3 + HCl

(Step A)

OR

CH4 + Cl CH3Cl + H

(Step B)

(i)

Use the following data to calculate a value for the enthalpy change for each of the Steps, A and
B.
Bond

Mean bond
enthalpy / kJ mol1

CH

+ 413

C Cl

+ 346

H Cl

+ 432

Enthalpy change for Step A

CH4 + Cl CH3 + HCl

Answer .......................kJ mol1

Enthalpy change for Step B

CH4 + Cl CH3Cl + H

Answer .......................kJ mol1

(3)

(ii)

Use your answer to (i) to justify which of the Steps, A or B, is the more likely.
...........................................................................................................................
...........................................................................................................................
(1)

(f)

Another halogenoalkane, bromomethane, CH3Br, is a toxic gas used to protect plants against insects.
Health and Safety advice states that concentrations above 5 parts per million (ppm) by volume of this
gas are harmful.

A research laboratory contains 2.5 105 dm3 of air. Calculate the maximum volume of
bromomethane, in dm3, allowed in the laboratory to comply with the advice given.
(1)
(Total 11 marks)

79.

This question is about four hydrocarbons with molecular formulae as shown.

A

C2H2

C3H6

C3H8

C4H10

(a)

Which hydrocarbon has the same empirical formula as its molecular formula?
A
B
C
D
(1)

(b)

Which has a molecular ion in the mass spectrum at mass/charge ratio = 58?
A
B
C
D
(1)

(c)

Which is neither an alkane nor an alkene?

A
B
C
D
(1)

(d)

Which could be 2-methylpropane?

A
B
C
D
(1)
(Total 4 marks)

80.

This question is about the following organic compounds with skeletal formulae as shown:

Br

Br

(a)

Which compound could be made from one of the others in an addition reaction?
A
B
C
D
(1)

(b)

Which compound has EZ isomers?

A
B
C
D
(1)
(Total 2 marks)

82.

Which of the following is the correct name for the compound below?
Cl

CH3
C

CH 3

Z-3-chlorobut-2-ene

E-3-chlorobut-2-ene

E-2-chlorobut-2-ene

Z-2-chlorobut-2-ene
(Total 1 mark)

83.

Propene can be used to make other important chemical products. The processes involved can be summarised
in the diagram:

CompoundA

CH2(OH)CH(OH)CH3
+HBr
Reaction 1

Reaction 2
CH2 CH

CH3

Propene

Reaction 4
+H2/Ni

Reaction 3

poly(propene)

CH3CH2CH2Cl
Reaction 5
(a)

(i)

Propane
CH 3CH2CH3

Give the mechanism for Reaction 1.

(3)

(ii)

Explain why compound A and not its structural isomer is the major product in Reaction 1.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(iii)

Name compound A formed in Reaction 1.

Name .................................................................................................................
(1)

(b)

What is added in Reaction 2 to make the product CH2(OH)CH(OH)CH3?

.....................................................................................................................................
(1)

(c)

Complete the balanced equation for the formation of poly(propene) in Reaction 3 using displayed
formulae.
n(CH2

CHCH3)

(2)

(d)

Poly(propene) fibres can be used to make fleece which is used at several horse racing courses to
prevent the ground becoming frozen.
State one advantage of using poly(propene) instead of natural fibres of similar cost.
.....................................................................................................................................
.....................................................................................................................................
(1)

(e)

(i)

One stage in the mechanism of Reaction 5 is shown below.

CH3CH2CH3 + Cl CH3CH2CH2 + HCl
What is this step?
...........................................................................................................................
(1)

(ii)

Give the name or formula of the trace product present in the final mixture which gives evidence
for this mechanism.
...........................................................................................................................
(1)
(Total 11 marks)

107. (a)

(i)

State TWO features that members of a homologous series have in common.

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

Name the homologous series to which propene belongs.

...........................................................................................................................
(1)

(iii)

Propene can be converted into a mixture of 2-chloropropane (as the major product) and 1chloropropane.
Classify the reaction involved and identify the reagent required.
Classification ....................................................................................................
Reagent .............................................................................................................
(2)

(b)

Define the term structural isomers.

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

.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)

(c)

1-chloropropane and 1-bromopropane both react with ammonia to give 1-propylamine.

State and explain, in terms of bonding and kinetics, which of 1-chloropropane and 1-bromopropane
would react faster with ammonia.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)

(d)

1-chloropropene, CH3CH

CHCl, can be polymerised to form poly(1-chloropropene).

Draw the repeat unit of poly(1-chloropropene).

(2)

(e)

Explain why 1-chloropropene exists as two different geometric isomers, but propene does not.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 14 marks)

108. (a)

Consider the following series of reactions.

reaction1
reaction 2
CH2OHCH2OH
CH2 CH2
CH2BrCH2Br
Ethene
Compound A
Compound B

(i)

Identify the reagent required for reaction 1.

...........................................................................................................................
(1)

(ii)

Name compound B.
...........................................................................................................................
(1)

(iii)

Identify the TWO reagents required for reaction 2.

...........................................................................................................................
...........................................................................................................................
(2)

(iv)

Compound A can be oxidised by heating with an acidified solution of potassium

dichromate(VI).
Give the colour change that would be observed and draw the full structural formulae of TWO
possible oxidation products, showing all bonds.
Colour from ................................................ to ................................................
Oxidation products

(3)

(v)

Suggest the name or formula of a compound that would be obtained if compound B were
reacted with ethanolic potassium hydroxide.
...........................................................................................................................
(1)

(b)

(i)

Compound B can be produced by reacting ethane with bromine in the presence of ultra-violet
light.
Suggest why a good yield of compound B would not be obtained and identify another organic
product that would be formed during the reaction.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

Write an equation for the complete combustion of ethane.

...........................................................................................................................
(2)

(iii)

Define the term empirical formula.

...........................................................................................................................
...........................................................................................................................
(1)

(iv)

Give the empirical formula for ethane.

...........................................................................................................................
(1)

(v)

Give the formula of an alkane, containing more than one carbon atom, whose molecular and
empirical formulae are the same.

(1)
(Total 15 marks)

137. This question concerns the compounds and reactions shown in the following reaction scheme.

CH3 H
CC
H

CH3
Step 5

Step 1

C=C
H

H n
E

CH3 H

HCCH

Cl

Step 4

Step 2

CH3 H
HCCH
Br

CH3 H
Step 3

H
D

(a)

HCCH
OH

From the compounds, A to E, state

(i)

which is a member of the same homologous series as pent-1-ene.

...........................................................................................................................
(1)

(ii)

which are described as secondary compounds.

...........................................................................................................................
(2)

(b)

Give the systematic name for

(i)

compound D ..........................................................................................................
(1)

(ii)

compound E ............................................................................................................
(1)

(c)

(i)

What reagent and conditions would you use for step 4?

Reagent .............................................................................................................
Conditions .........................................................................................................
(2)

(ii)

What type of reaction is this? ................................................................................

(1)

(d)

Compound B could be made from chlorine and propane in the presence of sunlight.
(i)

Write an equation to represent the initiation step in this chain reaction.

(1)

(ii)

Write an equation for the overall reaction to produce B in this way.

(1)

(iii)

Another possible product of this reaction has the following structural formula.
H3CCHCH3
H3CCHCH3

Name this compound ........................................................................................

Suggest how this compound formed in the reaction mixture.

Name the type of step involved in its formation.

...........................................................................................................................
(3)
(Total 13 marks)

141. A gaseous hydrocarbon, W, is a product formed in the cracking of eicosane, C20H42.

W decolourises bromine, forming compound X.
When X is reacted with aqueous potassium hydroxide, compound Y is formed.

When a solution of Y is refluxed with an excess of acidified potassium dichromate(VI), compound Z is

formed.
Compound Z contains carbon, hydrogen and oxygen only.
(a)

(i)

On complete combustion, 0.10 g of Z produced 53 cm3 of carbon dioxide and 0.020 g of water
at room temperature and pressure.
Calculate the empirical formula of compound Z.
[Molar volume of a gas is 24 000 cm3 mol1 at room temperature and pressure]

(3)

(ii)

The molar mass of Z is 90 g mol1. Find the molecular formula of Z.

(1)

(iii)

A solution made by dissolving 0.900 g of compound Z in water is titrated with sodium

hydroxide solution. 20.0 cm3 of sodium hydroxide solution of concentration 1.00 mol dm3 is
required for complete neutralisation.
Deduce the structural formula of compound Z.

(2)

(iv)

Deduce the structural formulae of compounds W, X, and Y.

(3)

(v)

Suggest a balanced equation for the cracking of eicosane.

(1)

(b)

Compound Y can be made in one step from compound W.

State the reagents needed for this reaction.
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 12 marks)

143. Bromine needs ultraviolet radiation to react with ethane, C2H6, but reacts with ethene, C2H4, in the dark.
(a)

Complete the equations.

(i)

C2H6 + Br2 ....................................................................................................

(1)

(ii)

C2H4 + Br2 ....................................................................................................

(1)

(b)

(i)

Identify and state the type of covalent bond in the hydrocarbon molecules that are broken
during these two reactions.
Ethane
bond broken ...................................... type ......................................
Ethene
bond broken ...................................... type ......................................
(2)

(ii)

Use your answer to (b)(i) to suggest why the reaction of bromine with ethene occurs more
readily than with ethane in the dark.
...........................................................................................................................
...........................................................................................................................
(1)
(Total 5 marks)

146. This question is about the chemistry of propane, C3H8.

Propane is sold for use as a fuel for camping stoves. On complete combustion it forms carbon dioxide and
water.
(a)

The enthalpy change of combustion of propane, Hc, can be measured by burning a known mass of
propane below a container of water and measuring the temperature rise of the water.
The heat capacity of the apparatus (the energy required to raise the temperature of the apparatus by 1
C) is found by calibrating it with a fuel with known enthalpy change of combustion.
The results of an experiment are shown below.
Mass of propane burned
Temperature of water at start
Final temperature of water
Heat capacity of apparatus

(i)

0.500 g
21.0 C
39.0 C
1.35 kJ C1

Calculate the number of kilojoules of energy transferred when the 0.500 g sample of propane
burns in this experiment.
(1)

(ii)

Use your answer to (i) to calculate Hc for propane in kJ mol1. Give your answer to three
significant figures.
Use the Periodic Table as a source of data.

(2)

(iii)

The Book of data gives the value of Hc for propane as 2220 kJ mol1.
Calibrating the apparatus means that the answer you calculated in (ii) allows for errors due to
heat loss.
Suggest the other main source of error which makes the experimental result different from the
data book value.
...........................................................................................................................
...........................................................................................................................
(1)

(b)

A value of Hc for propane can be calculated using mean bond energies and the Hess cycle below.
(i)

Complete the Hess cycle, and use the mean bond energies to calculate H1.
Hence calculate Hc.
Mean bond energies
/kJ mol1
C=O

805

HO

464
Hc

C3H8 (g) + ..........O2 (g)

+6490 kJ mol1

3CO2 (g) + 4H2O(g)

H1 = ........................................

3C(g) + 8H(g) + ..............................

Hc = ................................................................................................................

(3)

(ii)

Give ONE reason why the value you calculated in (b)(i) also differs from the value for the heat
of combustion of propane in the Book of data.
...........................................................................................................................
...........................................................................................................................
(1)

(c)

When propane reacts with chlorine in the presence of ultraviolet light one of the products is 2chloropropane.
(i)

Name the mechanism and type of this reaction.

Mechanism .......................................................................................................
Type ..................................................................................................................
(2)

(ii)

In this reaction a small quantity of an alkane, C6H14, is produced.

Explain how this occurs. Include an equation in your answer.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(d)

2-Chloropropane and 2-iodopropane are both colourless liquids at room temperature.

They can be distinguished by their reactions with aqueous silver nitrate.
(i)

What would you see when the reaction is carried out with each halogenoalkane?
2-chloropropane ...............................................................................................
2-iodopropane ..................................................................................................
(2)

(ii)

Write an ionic equation showing how silver ions react in the mixture made from 2-iodopropane
and aqueous silver nitrate. Include state symbols in your answer.

(2)

(iii)

Both 2-chloropropane and 2-iodopropane form the same organic product in the reaction with
aqueous silver nitrate.
Name, or give the structural formula of, this organic product.
...........................................................................................................................
(1)
(Total 17 marks)

147. This question is about some of the chemicals used in car engines and their reactions.
(a)

Compound X, shown below, is one component of petrol.

H

CH3

HCCCCCH
H

CH3

CH3 H

(i)

Name X.
...........................................................................................................................
(1)

(ii)

Give the empirical formula of X.

...........................................................................................................................
(1)

(iii)

X can be made by cracking decane, C10H22.

Assuming only one other product forms in a cracking reaction, deduce the molecular formula
of this other product.

(1)

(iv)

What is the sign of the enthalpy change for the reaction in which decane is cracked? Give a
reason for your answer.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(v)

If the air supply in a car engine is poor, there is not enough air for carbon dioxide to be
produced.
Use this information to suggest ONE possible equation for the combustion of X in this engine.
Use the molecular formula of X in your equation.

(2)

(b)

When air enters a car engine, as well as the fuel burning, nitrogen and oxygen can react to form
nitrogen(II) oxide.
N2(g) + O2(g)
(i)

2NO(g)

H = + 180 kJ mol1

What, if any, is the effect on the percentage of nitrogen(II) oxide in an equilibrium mixture of
these three gases if the pressure and temperature are increased?
Explain your answers.

Increase in pressure
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
Increase in temperature
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(ii)

In a car exhaust pipe, nitrogen(II) oxide passes over a catalytic converter.

The following reaction occurs.
2NO(g) + 2CO(g) N2(g) + 2CO2(g)

H = 746 kJ mol1

Explain why this reaction speeds up when the car engine has been running for a few minutes.
...........................................................................................................................
...........................................................................................................................
(1)

(iii)

A textbook says The catalytic converter converts the gases coming out of the engine into less
harmful ones.
State, with a reason, which of the four gases in the equation in (ii) you consider to be least
harmful.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(1)

(iv)

The diagram below shows the reaction profile for the change which occurs in the catalytic
converter.

Energy

2NO(g) + 2CO(g)
N 2 (g) + 2CO 2 (g)

Progress of reaction

On the diagram, show the activation energy, EA.

Add a line showing the reaction profile if no catalyst is present.
(2)
(Total 12 marks)

151. (a)

(i)

Compound W contains, by mass, 12.77% C, 2.13% H, 85.1% Br.

Calculate its empirical formula.

(2)

(ii)

The relative molecular mass of W is 188. Deduce its molecular formula.

...........................................................................................................................
...........................................................................................................................
(2)

(iii)

Compound W reacts with aqueous potassium hydroxide to form a compound X. Compound X

is also formed by the reaction of ethene with aqueous alkaline potassium manganate(VII). Draw
the structural formula of X.

(1)

(iv)

Hence draw the structural formula of W.

(1)

(b)

Primary halogenoalkanes (RCH2X) react with aqueous hydroxide ions:

RCH2X + OH RCH2OH + X
The rate of reaction depends on the halogen and is in the order
RCH2I > RCH2Br > RCH2Cl
Explain, in terms of bond enthalpies and kinetic factors, why this difference in rate is observed.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)
(Total 9 marks)

158. (a)

The molecule isoprene has the displayed formula

H
H

C C
H

(i)

Give the systematic name of isoprene.

...........................................................................................................................
(2)

(ii)

What colour change occurs when aqueous bromine solution is added to isoprene?
From ..................................................... to .......................................................
(1)

(iii)

State the type and mechanism of this reaction.

Type ................................................ Mechanism .............................................
(2)

(iv)

Suggest the displayed formula of the product formed when excess bromine reacts with
isoprene in the dark.

(1)

(b)

Compound Q, an isomer of isoprene, has the structural formula

CH2 =CHCH2CH=CH2.
(i)

Give the name of the intermolecular force present in both isomers.

...........................................................................................................................
(1)

(ii)

Which isomer would you expect to have the higher boiling point? Justify your answer.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)
(Total 9 marks)

164. Bromine reacts with both ethane, C2H6, and ethene, C2H4.
(a)

The reaction of bromine with ethane occurs in ultraviolet light.

(i)

By what type of mechanism does this substitution reaction occur?

...........................................................................................................................
(1)

(ii)

Write the equation for a reaction of ethane with bromine.

(1)

(b)

Bromine reacts rapidly with ethene without the need for light.
(i)

Give the equation for this reaction using structural formulae.

(2)

(ii)

Name the product. ...........................................................................................

(1)

(c)

Explain, in terms of the bonding in the two hydrocarbons, why the reaction of bromine with ethene
occurs so much more readily than that with ethane.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(3)
(Total 8 marks)

165. (a)

(i)

Draw the structural formulae of the two geometric isomers of but-2-ene, C4H8.

(2)

(ii)

Explain, in terms of structure and bonding, why but-2-ene exists as two geometric isomers
whereas but-1-ene does not.
...........................................................................................................................
...........................................................................................................................

...........................................................................................................................
...........................................................................................................................
(3)

(iii)

Draw the structural formula of another isomer with formula C4H8.

(1)

(b)

Alkenes can be used to make polymers.

(i)

Draw enough of the chain of poly(propene) to make its structure clear.

(2)

(ii)

Explain why poly(alkenes) cause problems when they are disposed of in a landfill site.
...........................................................................................................................
...........................................................................................................................
(2)
(Total 10 marks)

173. (a)

Name the homologous series to which the organic compound CH2=CHCH3 belongs.
.....................................................................................................................................
(1)

(b)

Write the structural formula of a member of the series named in (a) which contains four carbon atoms.
.....................................................................................................................................
(1)
(Total 2 marks)

175. (i)

Draw the displayed formula of propene, C3H6.

(1)

(ii)

Draw a dot and cross diagram for propene. You should show outer shell electrons only.

(1)
(Total 2 mark)

176. An addition polymer has the structure shown below.

CH3 H
C

CH3 H n
Give the structural formula and the name of the monomer from which this polymer is made.
Structural formula

Name .....................................................................................................................................
(Total 2 marks)

177. (a)

Calculate the enthalpy change of atomisation, Hat, in kJ mol1, for but-2-ene,

CH3CH CHCH3
CH3CH

CHCH3(g) 4C(g) + 8H(g)

Use the following average bond energies.

CC
C C
CH

Average bond energy

/kJ mol1
+347
+612
+413

(3)

(b)

The enthalpy changes of atomisation and the boiling points of some alkenes are shown below.
Hat
/kJ mol1

Boiling point
/C

Ethene, C2H4

+2260

103.6

Propene, C3H6

+3440

47.3

Alkene

6.2

But-1-ene, C4H8

(i)

Pent-1-ene, C5H10

+5800

+30.0

Hex-1-ene, C6H12

+6990

+63.4

On the grid below, plot values for the enthalpy change of atomisation (vertical axis) against the
number of carbon atoms in the alkene molecule (horizontal axis).
(One page of graph paper should be provided).
(3)

(ii)

Explain why these enthalpy changes rise regularly.

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(iii)

Use your graph to estimate the value of the enthalpy change of atomisation for
but-1-ene.
....................................... kJ mol1
(1)

(c)

(i)

Which intermolecular force occurs between alkene molecules?

...........................................................................................................................
(1)

(ii)

Explain why the boiling points increase from ethene to hex1ene.

...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(iii)

There are two boiling points for CH3CH

this?

CHCH3, but only one for CH3CH2CH

CH2. Why is

...........................................................................................................................
...........................................................................................................................
(1)

(iv)

2-methylbut-1-ene, CH 3 CH 2 C

CH 2 , is an isomer of pent-l-ene.

CH3

Predict which of these isomers has the higher boiling point. Justify your answer.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
(2)

(d)

By considering the intermolecular forces in water, suggest why liquid alkenes do not mix with water.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
(2)
(Total 17 marks)

182. But-1-ene undergoes the following reactions:

(a)

State the reagent and conditions needed for Reaction 1.

Reagent ........................................................................................................................
Conditions ....................................................................................................................
(3)

(b)

(i)

The reagent in Reaction 2 is gaseous hydrogen bromide.

Draw the full structural formula of compound A.

(1)

(ii)

What type of reagent is hydrogen bromide in this reaction?

......................................................................................................................
(1)

(c)

Identify the reagent needed for Reaction 3.

................................................................................................................................
(1)

(d)

But-1-ene can be used to make an addition polymer.

Draw the repeating unit of the polymer.

(2)
(Total 8 marks)

183. (a)

2,2,4-trimethylpentane, C8H18, is one of the hydrocarbons present in petrol.

(i)

Draw the structural formula of 2,2,4-trimethylpentane.

(1)

(ii)

To which homologous series does 2,2,4-trimethylpentane belong?

......................................................................................................................
(1)

(b)

(i)

Define the term standard enthalpy of combustion.

......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(3)

(ii)

Write the equation to represent the complete combustion of butane, C4H10.

......................................................................................................................
(2)

(c)

The enthalpies of combustion of some compounds in kJ g1 and kJ cm3 are given below.
Compound

Hc /kJ g1

0.12

Butane, C4H10(g)

(i)

Hc /kJ cm3

Ethanol, C2H5OH(l)

30

21

2,2,4-trimethylpentane, C8H18(l)

48

33

The standard enthalpy of combustion of butane is 2877 kJ mol1.

Calculate the enthalpy of combustion of butane in kJ g1.

(2)

(ii)

Use the information in the table to compare the advantages and disadvantages of these three
compounds as fuels for a motor vehicle.
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(4)
(Total 13 marks)

186. (a)

Pent-1-ene, CH3CH2CH2CH=CH2, polymerises in a similar manner to ethene.

(i)

Draw enough of the chain of poly(pent-1-ene) to make the structure of the polymer clear.

(2)

(ii)

Give the mechanism for the polymerisation of pent-1-ene, using a peroxide initiator ROOR
that produces RO radicals. Show only the initiation and two propagation steps.
Include the use of an appropriate type of arrow to show the movement of an electron.

(4)

(b)

Pent-1-ene reacts with hydrogen bromide to give 2-bromopentane as the major product.
(i)

Give the mechanism for this reaction.

(3)

(ii)

By considering the nature of the intermediates in this reaction, explain why the major product is
2-bromopentane rather than 1-bromopentane.
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(2)

(c)

Molecules of 2-bromopentane are chiral. If a single isomer of 2-bromopentane is reacted with

hydroxide ions, the SN1 reaction that results gives pentan-2-ol, but the product mixture shows no
optical activity.
(i)

How would you test for optical activity?

......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(2)

(ii)

Explain, in terms of the reaction mechanism, why the product mixture does not show optical
activity.
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
......................................................................................................................
(3)
(Total 16 marks)

187. Consider the following reaction scheme:

(a)

(i)

State the catalyst that is needed for Step 1.

......................................................................................................................
(1)

(ii)

Suggest a synthetic pathway that would enable you to make ethanoyl chloride from ethanol in
two steps. You should give reagents, conditions and the structure of the intermediate compound.
Experimental details and balanced equations are not required.

(4)

(b)

Give the reagents and conditions needed for:

(i)

Step 2 ...........................................................................................................
......................................................................................................................
(2)

(ii)

Step 3 ...........................................................................................................
......................................................................................................................
(3)