AS LEVEL CHEMISTRY

2.1.3 ALKENES

ASSESSED HOMEWORK

Answer all questions

Max 63 marks

Name ……………………………………………………………..

Mark ……../63 ……....% Grade ………

Paddington Academy 1
1. Cyclohexene can be converted into cyclohexane.

cyclohexene cyclohexane

Suggest suitable reagents and conditions for this reaction.

reagents ................................................................................................................
...

conditions ..............................................................................................................
...
[Total 2 marks]

2. Leaf alcohol reacts with bromine as shown in the equation below.

C H 3C H 2 C H 2C H 2O H C H 3C H 2 C H 2C H 2O H

C C + Br2 H C C H

H H Br Br

(i) State what you would see when bromine reacts with leaf alcohol.

.......................................................................................................................
..
[1]

(ii) Complete, with the aid of curly arrows, the mechanism involved in the
reaction between leaf alcohol and bromine. Show any relevant dipoles,
charges and lone pairs of electrons.
C H 3C H 2 C H 2C H 2O H C H 3C H C H 2C H 2O H

C C H C C H
H H Br Br

Br

Br
[4]
[Total 5 marks]

Paddington Academy 2
Paddington Academy 3
3. (a) Propan-2-ol can be formed by the hydration of an alkene in the presence
of a catalyst.

(i) Suggest a suitable catalyst for this reaction.

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[1]

(ii) This is an electrophilic addition reaction. What is meant by the term

electrophile?

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[1]

(b) A mechanism for the reaction in (a) is shown below.

CH3 H CH3 H CH3 H CH3 H

+
C C H C C H H C C H H C C H + H
step 1 + step 2 step 3
H H
O H O H
+
+ H H H
H

(i) Add ‘curly arrows’ to the mechanism to show the movement of

electron pairs in steps 1, 2 and 3.
[3]

(ii) Suggest, with a reason, the role of the H+.

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[1]
[Total 6 marks]

Paddington Academy 4
4. Propene, CH3CH==CH2, also reacts with HBr to produce two bromoalkanes that
are structural isomers.

C H 3 C H B rC H 3

C H 3C H CH2 + HBr

C H 3C H 2C H 2B r

Propyne, CH3CCH, reacts like propene. It reacts with HBr to give three
isomers with molecular formula C3H6Br2.

Draw the three isomers with molecular formula C3H6Br2.

[Total 3 marks]

Paddington Academy 5
5. Polymer A, shown below, can be formed from an alkene.
C2 H 5 H C 2H5 H C2 H 5 H C 2H 5 H

C C C C C C C C

H H H H H H H H

polymer A

(i) State the type of polymerisation involved in the formation of polymer A.

.......................................................................................................................
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[1]

(ii) Draw a circle around the repeat unit of polymer A.

[1]

(iii) Identify the monomer that formed polymer A.

[1]

(iv) Name polymer A.

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[1]
[Total 4 marks]

6. But-1-ene can undergo polymerisation. Draw a section of the polymer that can
be formed from but-1-ene. Show two repeat units.

[Total 2 marks]

Paddington Academy 6
7. Long chain alkanes, such as nonane, can be cracked into shorter chain alkanes
and alkenes.

(i) Write a balanced equation for the cracking of nonane into heptane and
ethene.

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..
[1]

(ii) Much of the ethene is then converted into ethanol.

Write a balanced equation for the conversion of ethene into ethanol. State
the essential conditions.

equation ........................................................................................................
..
[1]

conditions .....................................................................................................
...

.......................................................................................................................
..
[2]
[Total 4 marks]

8. Propene, CH3CH=CH2, is an alkene and undergoes an addition reaction with

bromine.

(i) State what you would see when propene reacts with bromine.

.......................................................................................................................
..
[1]

(ii) Complete, with the aid of curly arrows, the mechanism involved in the
reaction between propene and bromine. Show any relevant dipoles and
charges.

H3C  CH ==CH2

Br

Br
[4]
[Total 5 marks]

Paddington Academy 7
Paddington Academy 8
9. (a) Hex-3-ene reacts with Br2 to produce 3,4-dibromohexane.

Describe, with the aid of curly arrows, the movement of the electrons in
the mechanism.

Show the intermediate, any relevant dipoles and lone pairs of electrons.

H H H H

C C C 2H 5 C C C 2H 5

C 2H 5 C 2H 5 Br Br
Br

Br

                                                      Intermediate                                  3,4-
dibromohexane
[4]

(b) The mechanism in (a) shows cis-hex-3-ene reacting with Br2. Trans-hex-3-
ene also reacts with Br2 to produce 3,4-dibromohexane.

(i) How does the structure of trans-hex-3-ene differ from that of cis-hex-
3-ene?

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..

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[1]

(ii) Explain why both cis and trans hex-3-ene react with Br2 to produce
the same structural isomer.

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..

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..

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[1]

Paddington Academy 9
 [Total 6 marks]

Paddington Academy 10
10. Chloroethene, CH2CHCl, is polymerised to form poly(chloroethene) commonly
known as pvc.

(i) Draw a section of pvc showing three repeat units. Put a bracket round one
repeat unit.

[2]

(ii) Polymers such as pvc are difficult to dispose of because they are non-
biodegradable. Increasingly, they are disposed of by combustion.

State the problem associated with the combustion of polymers such as

pvc.

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..

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[1]

(iii) State two ways in which chemists are trying to minimise the damage to
the environment caused by the disposal of halogenated plastics such as
pvc.

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..

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[2]
[Total 5 marks]

Paddington Academy 11
11. Body odour often begins with secretions from glands called apocrine glands,
which are most numerous in the armpits. Bacteria, which live in the armpits, use
these secretions to produce energy and many different waste products.
Scientists have isolated one of these waste products, compound E, which is
shown below.
H 3C H
C C
C H 3C H 2C H 2 C H 2O H
com pound E

Compound E contains two functional groups, one of which is a primary alcohol.

(i) Name the other functional group and state how you could test for it.

name of the other functional

group .................................................................

test ................................................................................................................
..

observation ...................................................................................................
..
[3]

(ii) Name compound E

.........................................................................................
[1]
[Total 4 marks]

12. (a) Compound A is a chloroalkene with the percentage composition by mass:

C, 24.7%; H, 2.1%; Cl, 73.2%.

(i) Calculate the empirical formula of compound A. Show your working.

[2]

(ii) The relative molecular mass of compound A is 145.5. Show that the
molecular formula is C3H3Cl3.

[2]

Paddington Academy 12
Paddington Academy 13
 (b) Compound A is one of six possible structural isomers of C3H3Cl3 that are
chloroalkenes. Two of these isomers are shown below as isomer 1 and
isomer 2.

H C H 2C l C l CH3

C C C C

Cl Cl C l Cl

iso m e r 1 iso m e r 2

(i) Draw two other structural isomers of C3H3Cl3 that are chloroalkenes.

[2]

(ii) Name isomer

1. ......................................................................................
[2]

Paddington Academy 14
 (c) All of the isomers in (b) readily polymerise.

(i) Draw a section of the polymer P that could be formed when isomer 2
polymerises.

Show two repeat units.

polymer P
[2]

(ii) Addition polymers can be difficult to dispose of.

State two general problems in the disposal of polymers and identify

an extra problem when disposing of polymer P.

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[3]
[Total 13 marks]

Paddington Academy 15
13. 2-Methylbut-1-ene can be formed by the partial hydrogenation of isoprene.

2-Methylbut-1-ene reacts with Br2 to produce 1,2-dibromo-2-methylbutane by an

electrophilic addition mechanism. The mechanism for the reaction is shown
below.

H 3C H 3C CH3

step 1 step 2
C CH2 C C H 2B r C H 3C H 2 C C H 2B r

C H 3C H 2 C H 3C H 2 Br
Br Br

Br

(i) In step 1, Br2 behaves as an electrophile. Explain what is meant by the

term electrophile.

.......................................................................................................................
..
[1]

(ii) Label any relevant dipoles and add ‘curly arrows’ to the mechanism to
show the movement of electron pairs in step 1 and in step 2.
[3]
[Total 4 marks]

Paddington Academy 16