Questions

Q1. This question is about alkenes.

(a) (i) Give the molecular formula of this alkene.(1)

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(ii) Explain why the alkene in (a)(i) exhibits geometric isomerism.(2)
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(b) Propene reacts with three different reagents.

(i) Give the reagent needed for Reaction 1.(1)

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(ii) Identify, by name or formula, the organic product A formed in Reaction 2.(1)

(iii) State the colour change that you would see when Reaction 2 is carried out.(1)

From ........................................................... to ...........................................................

(iv) Give the mechanism for Reaction 3. Use curly arrows and show any relevant dipoles and lone
pairs.(4)

(c) But-2-ene polymerizes to form poly(but-2-ene).

Draw a section of this polymer, showing two repeat units.
(1)
(d) Cyclohexanol forms cyclohexene in the following reaction.

(i) Calculate the percentage atom economy by mass for the production of cyclohexene.
(1)

(ii) Calculate the percentage yield if 10.20 g of cyclohexanol produced 6.15 g of cyclohexene.
(2)

(Total for question = 14 marks)

Q2. A propellant for a rocket consists of a fuel, kerosene, and an oxidizer, liquid oxygen.
(a) The formulae of some hydrocarbons present in kerosene are shown in the table below.

(i) Name the homologous series to which the compounds A, B, C and E belong.
(1)
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 (ii) Name the compound A.(1)
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(iii) Explain the term structural isomers, by reference to two molecules selected from the table
in part (a).(3)
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(iv) Give the molecular formula of the compound D.(2)

(b) In the petrochemical industry, other fuels are obtained by the cracking and reforming of kerosene.
Using appropriate letters, A to D, identify a molecule listed in the table that could be formed from E by
(i) cracking alone
(1)
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(ii) cracking and then reforming
(1)
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(c) Suggest how engine performance is improved by using a fuel containing the molecule that you have
identified in (b)(ii).
(1)
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(d) The energy density of a fuel is defined as the energy produced per kilogram of fuel.
Calculate the energy density of dodecane, C12H26, in kJ kg−1. Give your answer to two significant figures.
The enthalpy change of combustion of dodecane is −8086 kJ mol−1.
[Molar mass: C12H26 = 170 g mol−1]
(3)

energy density = ........................................................... kJ kg−1

(Total for question = 13 marks)

Q3.This question is about alkenes.
(a) Give the general formula for the homologous series of alkenes.(1)
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(b) Give the structural formula of the organic product formed when ethene, CH2=CH2, reacts with
(i) hydrogen
(1)

(ii) chlorine
(1)

(iii) acidified aqueous potassium manganate(VII)

(1)

(iv) bromine water

(1)

(c) When propene, CH3CH=CH2, reacts with hydrogen chloride, there are two possible products, a major
product and a minor product.
(i) Draw the displayed formulae of these products.
(2)

(ii) Give the mechanism for the reaction of propene with hydrogen chloride which forms the major
 product.
(3)

(d) Propene can be polymerized.

(i) Write a balanced equation for the polymerization of propene to form poly(propene), drawing the
displayed formula of the repeat unit of poly(propene).
(3)

(ii) State a problem associated with the disposal of waste poly(propene).(1)

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(e) Standard enthalpy changes of combustion can be used to calculate the standard enthalpy change of
formation of propene.

Values for some standard enthalpy changes of combustion, are shown in the table below.

(i) Complete the Hess cycle below to enable you to calculate from combustion data.
(1)

(ii) Calculate in kJ mol−1.

 (2)

standard enthalpy change of formation of propene = ........................................................... kJ mol−1

(Total for question = 17 marks)
Q4. 100 cm3 of methane, CH4, is completely burned in 400 cm3 of oxygen.
What is the final volume of the gas mixture, in cm3, when all volumes are measured at room temperature
and pressure?
A 100 B 200 C 300 D 400
(Total for question = 1 mark)
Q5. This question is about the gases propane, C3H8, and butane, C4H10.
(a) (i) Propane and butane are both alkanes. Alkanes are said to belong to the same 'homologous series'.
Give two characteristics associated with homologous series.(2)
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(ii) Butane has a structural isomer but propane does not.
State what is meant by a structural isomer and explain why butane has a structural isomer but
propane does not.(2)
Structural isomer
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Explanation
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(b) Bottled propane is used as the fuel for the burners in hot air balloons. A hot air balloon carries 80 kg of
liquefied propane.
(i) Write the equation for the complete combustion of propane in air under standard conditions. State
symbols are not required.
(2)

(ii) Calculate the number of moles of propane in 80 kg.

(2)

(iii) The standard enthalpy change of combustion of propane, = –2220 kJ mol–1.

Calculate the heat energy, in joules, given out when 80 kg of propane burns completely.
(1)

(iv) The burners have a maximum power rating of 4800 W. (1 W = 1 J s–1)

Calculate the maximum time, in hours, that the balloon's fuel would last if the burners are used
continuously on full power with 80 kg of fuel.
(1)

(v) A student suggests that butane would be a better fuel for hot air balloons than propane because it
 has a more negative enthalpy change of combustion, = −2880 kJ mol–1.
Suggest two reasons why butane is not a better fuel than propane for hot air balloons.(2)
Reason one
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Reason two
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(c) The standard enthalpy changes of atomisation of propane and butane can be calculated. The
calculation requires their standard enthalpy changes of formation and the standard enthalpy changes of
atomisation of carbon and hydrogen.
(i) Complete the Hess cycle for the calculation of the standard enthalpy change of atomisation of
propane.
(1)

(ii) Calculate the standard enthalpy change of atomisation of propane,

[C3H8(g)]
Use the data below.
[C3H8(g)] = −104.5 kJ mol–1
[½H2 (g)] = +218 kJ mol–1
[C(s, graphite)] = +716.7 kJ mol–1
(3)

(iii) The standard enthalpy change of atomisation of butane can be calculated using the same method
as for propane. This value, together with the carbon-hydrogen bond energy, can be used to calculate the
carbon-carbon bond energy
ΔHat,298[C4H10(g)] = +5173.3 kJ mol–1.
E(C—H) = +412.3 kJ mol–1
Calculate the carbon-carbon bond energy.
(2)

(iv) Suggest why your answer differs from the mean bond energy for the carbon-carbon bond given in
 data books.(1)
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(Total for question = 19 marks)
Q6. What is the systematic name for the compound shown below?

A E-3-methylpent-2-ene B E-3-methylpent-3-ene
C Z-3-methylpent-2-ene D Z-3-methylpent-3-ene
(Total for question = 1 mark)
Q7. The skeletal formula of 3-methylcyclobut-1-ene is shown below.

What is the skeletal formula of 1-ethyl-3-methylcyclopent-1-ene?

(Total for question = 1 mark)

Q8. Crude oil is a source of alkanes.
(a) Name the process by which the hydrocarbons in crude oil are separated.
(1)
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(b) The alkane X is composed of straight-chain molecules, each with nine carbon atoms.
(i) Give the molecular formula of X.
(1)
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(ii) Y is a branched-chain isomer of X.
Y has eight carbon atoms in a straight-chain with one methyl group as a side-chain.
Draw the skeletal formula of one possible structure for Y.
Give the name of the structure that you have drawn.(2)
Skeletal formula:

Name: .............................................................................................................................................
(c) A reaction called cracking occurs when the alkane pentadecane, C15H32, is heated in the presence of a
catalyst.
(i) Give an equation to show the cracking of one molecule of C15H32 to form one molecule of ethene and
a molecule of one other product.
State symbols are not required.(1)
 (ii) In practice, cracking pentadecane forms a large number of products.
Suggest why this is so.(1)
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(d) In the petroleum industry, some straight-chain alkanes are processed to form cyclic hydrocarbons.
When octane is processed, each molecule of octane produces one molecule of a cyclic hydrocarbon,
C8H12, and three molecules of hydrogen as the only products.
(i) Complete the skeletal formula of one of the possible cyclic hydrocarbons.(1)

(ii) Suggest why the petroleum industry processes straight-chain alkanes to form cyclic hydrocarbons.
(1)
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(Total for question = 8 marks)
Q9. This question is about cyclohexene which can be used to show the reactions of the alkenes.

(a) (i) 1 cm3 of bromine water is shaken with 2 cm3 of cyclohexene in a test tube and the mixture allowed to
stand.
Describe what you would see before and after shaking.(3)
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(ii) Draw the skeletal formula of the major organic product of this reaction.
(1)

(b) Draw the skeletal formula and give the name of the organic product formed when cyclohexene reacts
with potassium manganate(VII) mixed with dilute sulfuric acid.(2)
Skeletal formula

Name ................................................................................
(c) Suggest the skeletal formula of the polymer that would be formed if cyclohexene polymerised. Show
two repeat units.
(2)

(Total for question = 8 marks)

Q10. Which compound has E-Z isomers?
A but-1-ene B but-2-ene
C 1,1-dichloroethene D 2-methylbut-2-ene
(Total for question = 1 mark)
Q11.
Which compound has an empirical formula different from its molecular formula?(1)

(Total for question = 1 mark)

Q12. When ethane reacts with chlorine, a mixture of products forms. Which product is the best evidence
for a free radical mechanism?
A HCl B C4H10 C C2H5Cl D C2H4Cl2
(Total for question = 1 mark)
Q13. Copolymers are formed from two different monomers.
The repeat unit of a copolymer is

This copolymer is formed from ethene and(1)

A propane. B propene. C 2-methylbutane. D 2-methylbut-1-ene.
(Total for question = 1 mark)
Q14.Which is a free radical?
A OH B OH− C OH2 D OH
(Total for question = 1 mark)
Q15. Which of the following is a reforming reaction?

(Total for question = 1 mark)

Q16. Which of the following is a step in the propagation stage of the chlorination of methane?
 (Total for question = 1 mark)
Q17. In the mechanism of the reaction of methane with chlorine to form chloromethane, which of the
following is a propagation step?
A •CH3 + •Cl →CH3Cl B •CH3 + Cl2→ CH3Cl + •Cl
C CH4 + •Cl → CH3Cl + •H D •CH3+ Cl2 → •CH2Cl + HCl
(Total for question = 1 mark)
Q18. What is the IUPAC name of the following hydrocarbon?

A 2,2-dipropylbutane B 4-methyl-4-propylhexane
C 2-ethyl-2-propylpentane D 4-ethyl-4-methylheptane
(Total for question = 1 mark)
Q19. Which of the following fuels, when burned, would make no significant contribution to climate change?
A Hydrogen
B Methane
C Petrol
D Coal

(Total for question = 1 mark)

Q20.

An electrophile is a species that

A can accept a pair of electrons to form a covalent bond.
B can donate a pair of electrons to form a covalent bond.
C always has a negative charge.
D always has a positive charge.

(Total for question = 1 mark)

Q21.

Alkenes react with hydrogen gas in the presence of a nickel catalyst.

0.2 mol of an alkene reacted completely with 19.2 dm3 of hydrogen gas at room temperature and pressure.
How many bonds are there in a molecule of this alkene?
[The molar volume of a gas is 24.0 dm3 mol−1 at room temperature and pressure]
A 4
B 3
C 2
D 1

(Total for question = 1 mark)

Q22.

In the United Kingdom, the limit for gaseous hydrocarbons in vehicle exhaust gases is 200 ppm.
What is the maximum volume of gaseous hydrocarbons allowed in 10 mol of exhaust gases, at room
temperature and pressure?
[Molar volume = 24 dm3 mol–1]
A 24 cm3
B 48 cm3
C 96 cm3
D 480 cm3

(Total for question = 1 mark)

Q23.

Propene reacts with hydrogen bromide to form

(1)
A a mixture of 1-bromopropane and 2-bromopropane
B 1,2-dibromopropane
C 2-bromopropan-1-ol
D 1-bromopropan-2-ol

(Total for question = 1 mark)

Q24.

Propene is an alkene which can be produced by cracking some of the hydrocarbons in crude oil.
(a) Draw a dot and cross diagram showing the bonding in propene.
Show outer electrons only.
(2)

(b) (i) Propene is one product of the cracking of decane, C10H22.

Write the equation for the reaction in which one mole of decane is cracked to produce one mole of
ethene, one mole of propene and one other product. State symbols are not required.
(1)

(ii) A synthetic rubber can be made by polymerizing a mixture of ethene and propene.
Draw the structural formula of the repeat unit of this polymer which forms from one molecule of each
alkene.
(2)

(c) Propene is also used to make propane -1,2-diol. Give the reagents and colour change when this
product is made at room temperature.
 (3)
Reagents
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Colour change from
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(d) The reaction of propene with bromine water is used as a test for the carbon-carbon double bond.
State the colour change in this test.
Draw the displayed formula of the organic product and give its name.
(3)
Colour change from
.................................................. to ..................................................
Displayed formula of product

Name .....................................................................
(e) Write the mechanism for the reaction of propene with hydrogen bromide to give the major product.
Include relevant dipoles.
(4)

*(f) Molecules of the element bromine, Br2, are not polar. Explain how bromine acts as an electrophile
when it reacts with propene.
(2)
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(g) In the United States of America, large deposits of shale gas have been discovered. This gas is trapped
in rocks and can be extracted by "fracking" which involves breaking up the rock with water under pressure.
Shale gas typically contains about 90% methane, mixed with about 3% ethane, 0.6% propane, 0.2%
butane and 0.2% pentane. The rest is hydrogen, nitrogen and carbon dioxide.
Suggest how the use of shale gas may affect the relative amounts of poly(ethene) and poly(propene)
which are produced in the USA and justify your answer.
(2)
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 (Total for question = 19 marks)

Q25.

Iodine monochloride, ICl, is an interhalogen compound. Molecules of iodine monochloride have a

permanent dipole. Alkenes react with ICl, under suitable conditions, in a similar way to the reaction of
alkenes with hydrogen chloride, HCl.
(a) Propene reacts with ICl to form two possible organic products.
One of these products is 2-chloro-1-iodopropane.

(i) Complete the mechanism below, by adding curly arrows and the intermediate species.
(3)

(ii) Classify the type and mechanism for the reaction in (a)(i).
(2)

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(iii) Draw the structure of the other possible organic product of the reaction of propene with ICl.
(1)

(b) Methane reacts with ICl, under suitable conditions, to form many products. Two of these products are
iodomethane and hydrogen chloride.
The reaction between methane and ICl is similar to that between methane and chlorine, Cl2.

(i) Suggest the essential condition needed for this reaction.

(1)

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*(ii) The mechanism for the reaction between methane and ICl involves three stages. One of these is
the third and final stage, called termination.
Describe the mechanism of the reaction to form iodomethane and hydrogen chloride.
In your answer, include:
 the type of reaction and mechanism
 the type of bond fission occurring
 the name and equation for the first stage of the mechanism
 the name and equations for the second stage of the mechanism
 one equation for a termination step
Curly (half-) arrows and state symbols are not required in your equations.
(7)
Type of reaction and mechanism
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Type of bond fission occurring

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(Total for question = 14 marks)

Q26.

Which reagent reacts with propene to form this compound?

(1)
A hydrogen peroxide solution
B oxygen and water
C aqueous sodium hydroxide
D acidified potassium manganate(VII)

(Total for question = 1 mark)

Q27.

Which hazard symbol must be displayed on a bottle containing hexane?

 (Total for question = 1 mark)

Q28.

How many straight chain isomers have the molecular formula C3H5Cl?
A 3
B 4
C 5
D 6

(Total for question = 1 mark)

Q29.

Compound X has the molecular formula C5H12.

(a) Draw the displayed formulae of the three structural isomers of C5H12.
(2)
(b) C5H12 reacts with chlorine to form a mixture of products.
(i) Classify the type and mechanism of this reaction.
(2)

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(ii) Write the equations for the two propagation steps for this mechanism. Use the molecular formula,
C5H12, in your first equation. Curly arrows are not required.
(2)

(iii) Write the equation for one termination step for this mechanism. Curly arrows are not required.
(1)

(c) An experiment was carried out to determine the enthalpy change of combustion of compound X, C5H12.
100.0 g of water was heated by burning 0.144 g of compound X.
The temperature rise of the water was 14.5°C.
(i) Calculate the energy transferred, in kJ, in this experiment.
Use the equation
heat energy produced (J) = mass of water × 4.18 × temperature change
(1)

energy transferred = ........................................................... kJ

(ii) Calculate the number of moles of compound X used in this experiment.

(1)

moles of X = ...........................................................

(iii) Calculate the enthalpy change of combustion of compound X. Include a sign and units in your
answer.
(2)

enthalpy change of combustion = ...........................................................

 (iv) The Data Book values for the enthalpy changes of combustion of the three structural isomers with
the formula C5H12 are:
−3509.1 kJ mol−1
−3503.4 kJ mol−1
−3492.5 kJ mol−1
The experimental value calculated in (c)(iii) is very different from these values.
Give two reasons, other than heat loss, for this large difference.
(2)

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(v) Explain why it is not possible to deduce which of the isomers is compound X by comparing this
experimental value and the Data Book values.
(1)

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*(d) Complete the Hess cycle and use it to calculate the enthalpy change of combustion of C5H12 from the
following data.
Show all of your working.

(4)
 (Total for question = 18 marks)

Q30.

What is the systematic name for the hydrocarbon shown?

(1)
A 2,2-dimethyl-4-ethylpentane
B 2-ethyl-4,4-dimethylpentane
C 3,5,5-trimethylhexane
D 2,2,4-trimethylhexane

(Total for question = 1 mark)

Q31.

In the reaction of methane with chlorine, ultraviolet light causes

A homolytic fission of the Cl—Cl bond in chlorine molecules.
B heterolytic fission of the Cl—Cl bond in chlorine molecules.
C homolytic fission of the C—H bond in methane molecules.
D heterolytic fission of the C—H bond in methane molecules.

(Total for question = 1 mark)

Q32.

Cordless hair-stylers use 2-methylpropane as a fuel. The 2-methylpropane reacts with oxygen on the
surface of a heated catalyst.
C4H10(g) + 6½O2(g) → 4CO2(g) + 5H2O(l)
(a) Draw the skeletal formula of 2-methylpropane.
(1)
(b) When the hair-styler is switched on, the catalyst is heated using a battery.
Suggest why the battery is not needed after the catalyst has been heated initially.
(2)
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(c) The standard enthalpy changes of formation for the three compounds are:

(i) The standard enthalpy change of formation of H2O(g) is –241.8 kJ mol–1. Explain why this is less
negative than the standard enthalpy change of formation of H2O(l).
(1)
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(ii) Use the data in the table to calculate the standard enthalpy change of combustion of 2-
methylpropane in kJ mol–1.
Show your method, which may involve the use of a Hess cycle.
Include a sign and units in your answer.
(3)

(iii) A refill canister for the cordless hair-styler holds 15 g of 2-methylpropane.

Calculate the energy in kJ which can be obtained from one canister.
(2)
(d) The enthalpy change of the reaction can also be calculated using the cycle below.

(i) Calculate the enthalpy change of the reaction using this cycle.
(1)
(ii) The enthalpy change of vaporization of water was one piece of data used to calculate the enthalpy
changes shown beside the arrows in the cycle. What other information was needed?
(1)
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(Total for question = 11 marks)

Q33.

For some reactions, the enthalpy change can be determined by experiment.

(a) Define the term enthalpy change of reaction.
(2)
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(b) An equation for the reaction between the two solids ammonium thiocyanate, NH4CNS, and barium
hydroxide, Ba(OH)2, is shown below.
2NH4CNS(s) + Ba(OH)2(s) → Ba(CNS)2(s) + 2H2O(l) + 2NH3(g)
The following apparatus was set up in order to determine the enthalpy change for the reaction.

In the experiment, 15.22 g of NH4CNS was reacted with an excess of Ba(OH)2. The reaction absorbed heat
energy from the surroundings. The temperature of the 100.0 g of water fell from 22.0°C to 16.5°C.

(i) Calculate the heat energy absorbed, in joules, during the reaction.
 Use the equation
Heat energy absorbed (J) = mass of water × 4.2 × temperature change
(1)

(ii) Calculate the number of moles of NH4CNS used in the experiment.

(1)

(iii) Calculate the enthalpy change of the reaction, in kJ mol−1, to two significant figures. Include a sign
in your answer.

2NH4CNS(s) + Ba(OH)2(s) → Ba(CNS)2(s) + 2H2O(l) + 2NH3(g)

(3)

(c) Standard enthalpy changes of reaction can also be calculated using mean bond enthalpies.

(i) What is meant by the term mean bond enthalpy?

(2)
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(ii) Describe the bonding in a double bond in terms of the different ways in which the orbitals
overlap.
You may draw a diagram if you wish.
(2)
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Space for diagram:

 (iii) Suggest why the mean bond enthalpy of a bond is less than twice the mean bond enthalpy of
a bond.
(1)
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(iv) Use the mean bond enthalpy data in the table, and the equation given below, to calculate a value
for the standard enthalpy change of combustion of propene.
(3)

Answer = ...........................................................kJ mol−

*(v) The Data Booklet value for the standard enthalpy change of combustion of propene is −2058 kJ mol−1.
Explain why the value calculated in (c)(iv) is less exothermic than the Data Booklet value.
(2)
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(Total for question = 17 marks)

Q34.

A molecule of Z has the following structure:

What are the total numbers of σ-bonds and π-bonds in a molecule of Z?

(Total for question = 1 mark)

Q35.

One of the isomers with the formula C4H8 is

Possible names for this isomer are

A cis-but-2-ene and E-but-2-ene.
B cis-but-2-ene and Z-but-2-ene.
C trans-but-2-ene and E-but-2-ene.
D trans-but-2-ene and Z-but-2-ene.

(Total for question = 1 mark)

Q36.

Which of the following shows geometric isomerism?

A propene
B but-1-ene
 C but-2-ene
D 2,3-dimethylbut-2-ene

(Total for question = 1 mark)

Q37.

Which of the following does not represent the structure of the compound 2-methylpent-2-ene?

(Total for question = 1 mark)

Q38.

Which is the structure of Z-1,2-dibromoprop-1-ene?

 (Total for question = 1 mark)

Q39.

(a) Ethane reacts with chlorine in the presence of ultraviolet light forming chloroethane, C2H5Cl and other
products.
(i) Ultraviolet light causes homolytic fission of chlorine molecules.
Draw a dot and cross diagram of a chlorine molecule and use it to explain what happens to the
molecule when homolytic fission occurs, naming the species produced.
(2)

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(ii) Write the equations for the two propagation steps which occur in the reaction producing
chloroethane.
(2)
Equation 1:

Equation 2:
 (iii) Write the equation for the termination step which produces a hydrocarbon as a product in this
reaction.
(1)

(b) Ethene also reacts with chlorine but by a different mechanism.

*(i) Describe how the π bond in ethene forms and explain why this bond causes ethene to take part in
addition reactions with halogens.
(2)
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*(ii) Write the mechanism for the reaction of ethene with chlorine.
Use curly arrows to show movements of electron pairs.
(3)

(iii) Name the product of the reaction of chlorine with ethene.

(1)
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(c) The halogenoalkene,1-chloroethene, is used to make a widely used polymer, poly(chloroethene),
commonly known as PVC.
Write a balanced equation for the polymerisation of 1-chloroethene to PVC.
Use displayed formulae to show the bonds in both the monomer and the polymer.
(2)

(Total for question = 13 marks)