21 This question is about cycloalkanes.

(a) When alkanes from crude oil are reformed, the products include cycloalkanes.
Write the equation for reforming hexane into cyclohexane using
skeletal formulae for the organic compounds.
(2)

(b) The skeletal formula of cycloalkane D is shown.

(i) Give the name of D.

(1)

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(ii) Give the molecular formula of D.

(1)

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 (c) There are four structural isomers of C6H12 with a ring of four carbon atoms.
One of these isomers is shown, in the first box.
Complete the skeletal formulae of the other three isomers.
(2)

(d) A cycloalkane, E, has a molar mass of 126 g mol−1.

Deduce the molecular formula of E.
(1)

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(e) A sample of gaseous cyclopentane with a volume of 25 cm3 was mixed with
250 cm3 of oxygen (an excess) and the mixture was ignited.
Only gaseous products were formed.

2C5H10(g) + 15O2(g) o 10CO2(g) + 10H2O(g)

Calculate the volume of each gas remaining after the reaction.

All the gas volumes were measured at the same temperature and pressure.
(3)

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 (f ) Cyclobutane, C4H8, reacts with chlorine in sunlight.
(i) Name the mechanism and type of reaction that is occurring.
(2)

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(ii) Complete the equation for the initiation step of this reaction mechanism.
Include appropriate curly arrows.
(2)

Cl Cl o

(iii) Write the equations for the two propagation steps to form chlorocyclobutane.
Use C4H8 as the formula for cyclobutane.
Curly arrows and state symbols are not required.
(2)

(iv) A small amount of a hydrocarbon forms in this reaction.

Deduce the skeletal formula of this hydrocarbon. Justify your answer.
(2)
Skeletal formula of product

Justification

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(Oct 19 Total for Question 21 = 18 marks)

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