13 Alkenes
OCR Chemistry A Exam-style questions
1 This question is about the reactions of cyclopentene, C 5H10.
a Draw the skeletal formula of the product made from Reaction 1 and the main
product from Reaction 2 in the boxes above. (2 marks)
b Give the reagents and conditions needed for Reaction 3 to take place.
(1 mark)
c Name the product of Reaction 3.
(1 mark)
d Reaction 2 demonstrates the test for unsaturation by the addition of bromine.
State the colour change you would expect to observe during this reaction.
Colour change from _______________ to _______________ (1 mark)
e All three reactions above have an atom economy of 100%. Explain why.
(1 mark)
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13 Alkenes
OCR Chemistry A Exam-style questions
2 Polybut-1-ene is a polymer that is insoluble in water. It is used for hot and cold
water pipes and is made by the polymerisation of the monomer but-1-ene.
a Write an equation to show this polymerisation reaction.
(2 marks)
b Polymers that are soluble in water have been developed for use as plastic
pouches to hold dishwasher liquid and laundry gels. A portion of one of these
polymer chains is shown below:
i Suggest the monomer of this polymer.
(1 mark)
ii Suggest why this polymer is soluble, but polybut-1-ene is insoluble in water.
(2 marks)
3 One method for disposing of waste poly(alkenes) is by combustion, generating
large amounts of heat.
a Give one possible advantage and one disadvantage to the environment of
disposing of polymers in this way.
(2 marks)
b Halogenated plastics such as poly(vinyl chlorides), PVC, can produce toxic
waste gases if combusted. One of these waste gases can be removed by a
reaction with sodium hydrogencarbonate.
Name this waste gas.
(1 mark)
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13 Alkenes
OCR Chemistry A Exam-style questions
c New polymers are being developed that will break down more easily in the
environment. One type is a biodegradable polymer.
Give an example of another type of degradable polymer and state what
makes these polymers break down.
(2 marks)
d Biodegradable polymers are often made from plant material and break down
through microbial action to produce carbon dioxide and water. Manufacturers
claim these types of polymers are carbon neutral.
Explain how the manufacturers can claim this and suggest why producing
these polymers is actually unlikely to be carbon neutral overall.
(2 marks)
4 The following alkene will undergo a reaction with hydrogen chloride to produce
two possible products.
a Name the alkene.
(1 mark)
b Name the type of mechanism for the reaction of this alkene with hydrogen chloride.
(2 marks)
c Draw the mechanism for the reaction that will produce the major product.
Use curly arrows, partial charges and charges where relevant. (4 marks)
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13 Alkenes
OCR Chemistry A Exam-style questions
d Explain, using Markownikoff’s rule, why this product is the major product.
(1 mark)
e Name the minor product formed.
(1 mark)
f Curly arrows can be used in mechanisms to show bond breaking. There are two types of
bond breaking: homolytic and heterolytic.
Which type of bond breaking in shown in the mechanism drawn in part c?
Explain your answer.
(2 marks)
5 The alkene methylpropene, shown below, is an unsaturated molecule that
contains a C=C double bond.
a The C=C double bond is made up of a σ-bond and a π-bond.
Draw a diagram to show how a π-bond forms when two orbitals on the
carbon atoms overlap. (2 marks)
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13 Alkenes
OCR Chemistry A Exam-style questions
b The bond angle, labelled a, in this molecule is 120°.
i What name is given to the shape around each carbon atom in this molecule?
(1 mark)
ii Explain why this bond angle is 120°.
(1 mark)
c Despite having a C=C double bond, this molecule cannot demonstrate E/Z
isomerism. Explain why.
(1 mark)
d Hex-2-ene has a molecular formula of C6H12. The skeletal formula for trans-
hex-2-ene is shown below:
i Draw the skeletal formula for cis-hex-2-ene.
(1 mark)
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13 Alkenes
OCR Chemistry A Exam-style questions
ii There are other aliphatic alkenes, besides hex-2-ene, which also have a
molecular formula of C6H12. Some of these alkenes can show E/Z
stereoisomerism.
Draw the structures of two other different alkenes, both with a molecular
formula C6H12, which can both show E and Z stereoisomers.
(2 marks)
e i Use the Cahn–Ingold–Prelog priority rules to identify whether the
following structure is the E or Z stereoisomer. Explain your answer.
(2 marks)
ii Why can this molecule not be labelled as either ‘cis’ or ‘trans’?
(1 mark)
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