1(a) This question is about cyclic organic compounds.

The table shows some information about cycloalkanes.

Cycloalkane Skeletal formula Boiling point / °C

Cyclopropane −33

Cyclopentane 49

Cyclohexane 81

The C–C–C bond angles in cyclohexane are 109.5°.

State and explain the shape around each carbon atom in cyclohexane.

shape _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

explanation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _

[2]

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 (b) In the presence of ultraviolet radiation, cyclohexane reacts with bromine.

A mixture of cyclic organic compounds is formed, including C6H11Br.

(i) Complete the table below to show the mechanism of the reaction between bromine and
cyclohexane to form C6H11Br.

Include all possible termination steps in your answer.

Step Equation

Initiation _______________________________________________

Propagation
_______________________________________________

_______________________________________________

Termination
_______________________________________________

_______________________________________________

_______________________________________________

[5]

(ii) The initiation step involves homolytic fission.

Explain why the initiation step is an example of homolytic fission.

[1]

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 (c) The reaction between cyclohexane and bromine in (f) also forms C6H10Br2.

(i) Write an equation, using molecular formulae, for the reaction of cyclohexane and bromine in the
presence of ultraviolet radiation to form C6H10Br2.

[1]

(ii) Name one of the structural isomers of C6H10Br2 formed in the reaction between cyclohexane and
bromine.

[1]

2 Alkanes are used as fuels.

(i) Construct an equation for the complete combustion of octane C8H18.

[1]

(ii) Combustion of 36.48 g of octane produced 2.50 mol of carbon dioxide.

Show that this combustion was incomplete.

[2]

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 3 This question looks at alkanes.

Ethane reacts with chlorine by radical substitution.

Describe fully, with equations, the mechanism for this reaction.

[5]

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 4 * The hydrocarbon propane can be reacted with chlorine to prepare 2-chloropropane, CH3CHClCH3,
by radical substitution.

Describe this reaction, including an overall equation and conditions, the mechanism with names for all
steps and the limitations of this method of preparation.

[6]

5 Give chemical explanations for the following statements.

The reaction of ethane with chlorine under UV radiation is a poor method for preparing a high yield of
chloroethane.

[1]

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 6(a) Alkane A, shown below, reacts with bromine in a radical substitution reaction.

Alkane A

In this reaction with bromine, monosubstitution of alkane A forms a mixture of organic products.

Show the structures of two monosubstituted organic products that are formed.

[2]
(b) With excess bromine, further substitution takes place.

Write an equation for the reaction of alkane A with excess bromine to produce
1,3-dibromo-2-methylpropane.

Use structures for the organic compounds.

[2]

7 The relative molecular masses and boiling points of some fuels are shown in Table 22.1.

Fuel Relative molecular mass Boiling point / °C

hexane 86 69
pentan-1-ol 88 138
heptane 100 98

Table 22.1

Write an equation for the incomplete combustion of heptane.

[1]

8(a) This question is about saturated hydrocarbons.

Compounds A, B and C are saturated hydrocarbons.

The structures and boiling points of A, B and C are shown below.

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 • Use the structures to explain what is meant by the term structural isomer.
• Explain the trend in boiling points shown by A, B and C in the table.

[5]

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 (b) Compounds A, B and C all react with chlorine in the presence of ultraviolet radiation to form organic
compounds with the formula C5H11Cl.

(i) Name the mechanism for this reaction.

[1]

(ii) Complete the table to show the number of structural isomers of C5H11Cl that could be formed from
the reaction of chlorine with A and B.

A B
Number of
structural isomers ........................ ........................
[2]

(iii) The reaction of compound A with excess chlorine forms a compound D, which has a molar mass of
175.5 g mol−1.

Draw a possible structure for compound D and write the equation for its formation from compound A.
Use molecular formulae in the equation.

Equation [2]

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 9 Under suitable conditions, butane, C4H10, reacts with chlorine by radical substitution. A mixture of
organic compounds is formed, including C4H9Cl , and compounds D and E.

(i) Complete the table below to show the mechanism for the initiation and propagation stages of the
reaction of C4H10 with chlorine to form C4H9Cl .

In your equations, use molecular formulae and ‘dots‘ (·) with any radicals.

Equation
Initiation
Conditions

→
Propagation

[3]

(ii) Organic compound D is formed by substitution of all the H atoms in butane by Cl atoms.

Write the equation for the formation of compound D from butane.

Use molecular formulae.

[1]

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 (iii) Organic compound E is formed by the substitution of some of the H atoms in butane by Cl atoms.

A chemist found that 0.636 g of compound E has a volume of 78.0 cm3.

Under the conditions used, the molar gas volume is 32.5 dm3 mol-1.

Determine the molecular formula of compound E.

molecular formula = ......................................................... [3]

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 10(a The structure of hydrocarbon A is shown below.
)

Complete the table to show the mechanism for the reaction of hydrocarbon A with Br2 to form
(CH3)3CCHBrCH3.

Use skeletal formulae for all organic compounds.

Use ‘dots’ (●) to show the position of unpaired electrons.

[3]
(b) State two limitations of using radical substitution in organic synthesis.

[2]

END OF QUESTION PAPER

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