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Halogenoalkanes and Alcohols HW
Halogenoalkanes and Alcohols HW
2.2.1 ALCOHOLS
2.2.2 HALOGENOALKANES
(no oxidation or esterification reactions)
ASSESSED HOMEWORK
Max 88 marks
Name ……………………………………………………………..
Paddington Academy 1
1. Ethanol has a relatively high boiling point. This can be explained in terms of
intermolecular hydrogen bonds.
Draw a second molecule of ethanol alongside the one drawn below and show
how a hydrogen bond could be formed. Clearly show any relevant dipoles and
lone pairs of electrons.
H O
C H 2C H 3
[Total 3 marks]
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[Total 2 marks]
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[2]
(b) In this question, one mark is available for the quality of written
communication.
Future supplies of ethanol are likely to come from glucose rather than from
ethene. Explain why.
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Paddington Academy 2
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[9]
Quality of Written Communication [1]
[Total 12 marks]
Paddington Academy 3
4. In this question, one mark is available for the quality of use and organisation of
scientific terms.
Different cars require different grades of petrol. The first stage in the production
of petrol in an oil refinery is to fractionate the crude oil. After that, refineries
carry out further processes.
Explain why, in the long term, ethanol could replace oil-based fuels.
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Paddington Academy 4
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[10]
Quality of Written Communication [1]
[Total 11 marks]
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[Total 2 marks]
Paddington Academy 5
(a) Answer the following questions by referring to the compounds A-F.
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[1]
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[1]
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and ..................................................
[1]
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and ..................................................
[1]
Paddington Academy 6
(b) Compound E can be dehydrated to form compound A. Complete a
balanced equation for this reaction.
H H H H
H C C C C H
H H O H H
[1]
name .............................................................................................................
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[2]
[Total 7 marks]
A B
reaction 1 reaction 2
H 3C CH2 CH3 H 3C CH2 CH2 Cl H 3C CH2 CH2 OH
C l 2 /uv light aque ous O H – / heat
reaction 3 ethanolic
O H – / heat
OH
polym erisation reaction 4
E H 3C CH CH2 H 3C CH CH3
C D
Paddington Academy 7
(b) In reaction 2, the aqueous OH– acts as a nucleophile.
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[1]
(ii) Complete, with the aid of curly arrows, the mechanism involved in reaction
2. Show any relevant dipoles.
OH–
[4]
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[2]
Compound B Compound D
[2]
Paddington Academy 8
[1]
[Total 15 marks]
OH
[1]
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[1]
[1]
Paddington Academy 9
(b) The reaction in stage 1 is difficult to control. One other possible chlorinated
product is 1,4-dichlorocyclohexane.This is shown below.
Cl
Cl
cyclohexane 1,4-dichlorocyclohexane
[1]
(ii) Two cyclic alkenes, C and D are formed in stage 3. C and D are
structural isomers. Suggest the structures of C and D.
[2]
[Total 6 marks]
Paddington Academy 10
9. This question is about the halogenoalkane 2-chlorobutane.
[1]
(ii) Describe, with the aid of curly arrows, the movement of the electrons in
the mechanism. Show any relevant dipoles, lone pairs of electrons and the
products.
[4]
[Total 5 marks]
(a) Describe, with the aid of curly arrows, the mechanism of the hydrolysis of
1-chlorobutane with OH–(aq) ions to produce butan-1-ol. Show any
relevant lone pairs of electrons and dipoles.
H H
C H 3C H 2C H 2 C Cl C H 3C H 2C H 2 C OH + ...................
H H
[4]
Paddington Academy 11
(b) Another halogenoalkane, H, has a relative molecular mass of 127 and has
the following composition by mass:
C, 37.8%; H, 6.3%; Cl, 55.9%.
[2]
[1]
(iii) Compound H can also be hydrolysed with hot aqueous alkali to form
butane-1,3-diol. Draw the structure of butane-1,3-diol
[1]
[1]
[Total 9 marks]
Paddington Academy 12
11. Halogenoalkanes are used in the production of pharmaceuticals, polymers and
flame retardants.
(iii) Calculate the percentage yield. Quote your answer to three significant
figures.
answer ……………………
[1]
[Total 4 marks]
Paddington Academy 13
12. Trifluorochloromethane, CF3Cl, is an example of a chlorofluorocarbon, CFC,
that was commonly used as a propellant in aerosols. Nowadays, CFCs have
limited use because of the damage caused to the ozone layer.
[1]
(ii) Predict an approximate value for the bond angles in a molecule of CF 3Cl.
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[1]
(iv) When CFCs are exposed to strong ultraviolet radiation in the upper
atmosphere, homolytic fission takes place to produce free radicals.
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[2]
(v) Suggest which bond is most likely to be broken when CF 3Cl is exposed to
ultraviolet radiation. Explain your answer.
bond ..............................................................................................................
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reason ...........................................................................................................
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[1]
(vi) Identify the two free radicals most likely to be formed when CF3Cl is
exposed to ultraviolet radiation.
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and ...........................................................
[2]
[Total 8 marks]
Paddington Academy 14
Paddington Academy 15
13. Oxygen-containing compounds can be added to improve the efficiency
and performance of fuels.
answer ……………………
[2]
[2]
[Total 4 marks]
Paddington Academy 16