Practice questions

1. When hydrogen bromide, HBr, reacts with propene, a higher percentage of 2-

bromopropane forms than 1-bromopropane. Which is the best explanation for this?
A 1-bromopropane is more stable than 2-bromopropane
B 2-bromopropane is more stable than 1-bromopropane
C a primary carbocation is more stable than a secondary carbocation
D a secondary carbocation is more stable than a primary carbocation
2. If propene, CH3CH=CH2, is reacted with aqueous acidified potassium manganate(VII)
the organic product is
A CH3CH(OH)CH2OH
B CH3CH(OH)CH3
C HOCH2CH2CH2OH
D CH3CH2CH2OH
3. Four of the reactions of propene are shown on the diagram below.

(a) Nickel is often used as the catalyst for Reaction 1. Use your Periodic Table to
select which of the following metals can be used instead of nickel to catalyse Reaction 1.

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A Potassium
B Calcium
C Gallium
D Palladium
(b) The name of the reagent and the product for Reaction 2 are

(c) What is formed in Reaction 3?

A Only 1-bromopropane
B Only 2-bromopropane
C A mixture of bromopropanes containing mainly 2-bromopropane
D A mixture of bromopropanes containing mainly 1-bromopropane
(d) A mixture of dilute sulfuric acid and which of the following reagents is needed for
Reaction 4?
A KOH
B KMnO4
C H2O2
D O2

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 (e) The reaction of propene in Reaction 4 can be classified both as

4. 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 C=C 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]
A4
B3
C2
D1
5. This question concerns the reaction of hydrogen bromide with propene.
(a) This reaction requires
A normal laboratory conditions.
B the presence of UV light.
C the presence of a suitable catalyst.
D heating under reflux.
(b) The reaction is best described as
A nucleophilic substitution.
B electrophilic substitution.
C nucleophilic addition.
D electrophilic addition.

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 (c) The major product of the reaction will be
A 1-bromopropane
B 2-bromopropane
C 1,2-dibromopropane
D 2-bromopropene
6. The repeat unit of a polymer is shown below.

The systematic name of the alkene monomer that forms this polymer is
A 2-methyl-3-ethylpropene
B 2-methylpent-2-ene
C 2-methylpent-3-ene
D 4-methylpent-2-ene
7. Poly(ethene) is a plastic material made by polymerizing the hydrocarbon ethene.
Which of the following is not true?
Pure poly(ethene) is
A solidified ethene.
B composed of carbon and hydrogen only.
C a long-chain compound.
D non-biodegradable.

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8. Which of the following equations shows the first step in the mechanism for the
reaction between hydrogen bromide and ethene?

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9. A section of a polymer is shown below.

What is the monomer for this polymer?

10. Alkenes are unsaturated hydrocarbons which, because of their reactivity, are important
industrial starting materials. Alkenes for industrial use are obtained by cracking alkanes.
(a) Write the equation for the cracking of decane (C10H22) to form 1 molecule of propene
as the only alkene.
(b) The carbon–carbon double bond in alkenes consists of a σ and a π bond.
(i) Explain, using diagrams, the difference between the σ and the π bond in the
carbon–carbon double bond of an alkene.
(ii) State the type and mechanism involved in the typical reaction of alkenes.
*(iii) By considering the strength and structure of the π bond, explain why alkenes are

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 more reactive than alkanes.
(c) When propene reacts with hydrogen bromide, there are two possible products.
(i) Draw a displayed formula of each of these products and label the major product.
(ii) Give the mechanism for the reaction of propene with hydrogen bromide which forms
the major product.
(iii) Explain, by referring to the mechanism, why the major product is formed.
d) The polymer poly(propene) is manufactured from propene.
(i) Write an equation for the polymerization, drawing the displayed formula of the repeat
unit of poly(propene).
(ii) UV radiation causes poly(propene) to degrade. Suggest one advantage and one
disadvantage of this.
11. This question is about the chemistry of alkenes, which are unsaturated hydrocarbons.
(a) State what is meant by the term unsaturated as applied to a hydrocarbon.
(b) An organic compound, X, is an unsaturated hydrocarbon with molecular formula C4H8.
(i) Draw the displayed formulae and give the names of two unbranched molecules with
molecular formula C4H8 which are E/Z isomers.
(ii) Both isomers react with a solution of acidified aqueous potassium manganate(VII).
State the colour change that you would observe when this reaction is carried out.
(iii) Draw the structure of the organic product of this reaction with either one of these
isomers.
(c) Another alkene is propene, C3H6.
Describe the mechanism for the addition reaction of propene with bromine, Br2, to form
C3H6Br2.
In your answer you should include:

• the name for the type of addition which occurs

• the name of the product
• the mechanism using curly arrows to show the movement of electron pairs.
(d) Propene can polymerize to form poly(propene).

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 (i) State, with a reason, the atom economy for this reaction.
(ii) Draw a section of this polymer, showing two repeat units.
12. 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.
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.
(ii) Classify the type and mechanism for the reaction in (a)(i).
(iii) Draw the structure of the other possible organic product of the reaction of propene
with ICl.

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13. This question is about alkenes.

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

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

(i) Give the reagent needed for Reaction 1.

(ii) Identify, by name or formula, the organic product A formed in Reaction 2.
(iii) State the colour change that you would see when Reaction 2 is carried out.
(iv) Give the mechanism for Reaction 3. Use curly arrows and show any relevant
dipoles and lone pairs.
(c) But-2-ene polymerizes to form poly(but-2-ene). Draw a section of this polymer,
showing two repeat units.
END