Download A-level Chemistry Question paper Unit 3/W - Introduction to

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General Certificate of Education
June 2009
Advanced Subsidiary Examination
CHEMISTRY
Unit 3(a) Introduction to Organic Chemistry
Wednesday 3 June 2009
CHM3/W
9.00 am to 10.00 am
For this paper you must have
● the Periodic Table/Data Sheet provided as an
insert (enclosed)
● a calculator.
For Examiner’s Use
Question
Mark
Question
Mark
1
Time allowed: 1 hour
2
Instructions
● Use black ink or black ball-point pen.
● Fill in the boxes at the top of this page.
● Answer all questions.
● Answer the questions in Section A and Section B in the spaces
provided. Answers written in margins or on blank pages will not
be marked.
● Your answers to Section B should be on the pages indicated.
● All working must be shown.
● Do all rough work in this book. Cross through any work you do not
want to be marked.
● The Periodic Table/Data Sheet is provided as an insert.
3
Information
● The maximum mark for this paper is 60.
● The marks for questions are shown in brackets.
● You are expected to use a calculator where appropriate.
● Write your answer to the questions in Section B in continuous prose,
where appropriate.
● You will be assessed on your ability to use good English, to organise
information clearly and to use specialist vocabulary, where
appropriate.
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5
6
7
8
Total (Column 1) →
Total (Column 2) →
TOTAL
Examiner’s Initials
Advice
● You are advised to spend about 45 minutes on Section A and about
15 minutes on Section B.
(JUN09CHM3W01)
APW/Jun09/CHM3/W
CHM3/W
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SECTION A
Answer all questions in the spaces provided.
1 Crude oil is a mixture which can be separated into fractions. These fractions contain
saturated hydrocarbons that belong to the homologous series of alkanes.
1
(a)
(i) Name the process by which crude oil can be separated into fractions.
...................................................................................................................................
(1 mark)
1
(a)
(ii) State what is meant by the term saturated, as applied to a hydrocarbon.
...................................................................................................................................
...................................................................................................................................
(1 mark)
1
(b) Each homologous series can be represented by a general formula.
State two other characteristics of homologous series.
Characteristic 1 .................................................................................................................
.............................................................................................................................................
Characteristic 2 .................................................................................................................
.............................................................................................................................................
(2 marks)
1
(c) Fractions from crude oil can be converted into different substances by catalytic
cracking or by thermal cracking.
1
(c)
(i) Explain what is meant by the term cracking.
...................................................................................................................................
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(2 marks)
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(c)
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(ii) Apart from the use of a catalyst, state how one of the conditions for catalytic
cracking differs from that used for thermal cracking.
...................................................................................................................................
...................................................................................................................................
(1 mark)
1
(c) (iii) State one way in which the products formed by catalytic cracking differ from
those formed by thermal cracking.
...................................................................................................................................
...................................................................................................................................
(1 mark)
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2 The alkanes are used mainly as fuels.
2
(a) The empirical formula and the molecular formula of undecane are both C11H24
2
(a)
(i) State what is meant by the term empirical formula.
...................................................................................................................................
...................................................................................................................................
(1 mark)
2
(a)
(ii) Give the molecular formula of an alkane with 15 carbon atoms.
...................................................................................................................................
(1 mark)
2
(a) (iii) State what is meant by the term fuel.
...................................................................................................................................
...................................................................................................................................
(1 mark)
2
(a) (iv) Write an equation for the complete combustion of undecane (C11H24).
...................................................................................................................................
(1 mark)
2
(b) Ethanol can also be used as a fuel in the engine of a motor car.
Write an equation for the incomplete combustion of ethanol to form carbon monoxide
and water only.
.............................................................................................................................................
(1 mark)
5
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3 The mechanism for the reaction of fluorine with difluoromethane (CH2F2) is a free-radical
substitution similar to the reaction of chlorine with methane.
3
(a) Write an equation for each of the following steps in the mechanism for the reaction of
fluorine with difluoromethane to form trifluoromethane (CHF3).
Initiation step
.............................................................................................................................................
First propagation step
.............................................................................................................................................
Second propagation step
.............................................................................................................................................
A termination step in which C2H2F4 is formed
.............................................................................................................................................
(4 marks)
3
(b) Heptafluoropropane (C3HF7) is used to extinguish fires that occur in electrical
equipment.
3
(b)
(i) Balance the following equation.
C3H8 + …… F2
3
(b)
C3HF7 + …… HF
(1 mark)
(ii) Draw the structure of one of the possible isomers of C3HF7
(1 mark)
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(c) Halon 1301 was used in fire extinguishers before the introduction of
heptafluoropropane. Halon 1301 is a compound which contains 8.1 % carbon and
53.7 % bromine by mass. The remainder of the compound is fluorine.
Calculate the empirical formula of Halon 1301.
.............................................................................................................................................
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(3 marks)
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4 The table shows five structural isomers.
Structure
Isomer 1
Name
CH2
H2C
CH2
H2C
CH2
CH2
Isomer 2
H
CH3CH2CH2
C
C
CH3
hex-2-ene
H
2-methylpent-1-ene
H
Isomer 3
CH3
CH3CH2CH2
C
C
H
Isomer 4
CH3
CH3CH2
C
C
CH3
3-methylpent-2-ene
H
Isomer 5
CH3
CH3
C
C
CH3
CH3
4
(a) Complete the table by naming Isomer 1 and Isomer 5.
4
(b) State what is meant by the term structural isomers.
(2 marks)
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(2 marks)
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(c)
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(i) State the type of structural isomerism shown by Isomer 1 when it is compared to
the other four isomers in the table.
...................................................................................................................................
(1 mark)
4
(c)
(ii) Identify the isomers from the table that exist as stereoisomers.
...................................................................................................................................
...................................................................................................................................
(2 marks)
4
(c) (iii) Draw the structure of a position isomer of hex-2-ene.
(1 mark)
4
(d) Name and outline a mechanism for the reaction of bromine with Isomer 5.
Name of mechanism ...........................................................................................................
Mechanism
(5 marks)
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5 Consider the following two reaction sequences.
KOH(aq)
CH3CHBrCH3
CH3CH(OH)CH3
2-bromopropane
K2Cr2O7/H2SO4
O
CH3
C
P
KOH(aq)
CH3CH2CH2Br
CH3CH2CH2OH
1-bromopropane
Q
CH3
R
K2Cr2O7/H2SO4
O
CH3CH2
C
H
S
K2Cr2O7/H2SO4
compound T
5
(a) Name and outline a mechanism for the conversion of 2-bromopropane into
compound P.
Name of mechanism ...........................................................................................................
Mechanism
(3 marks)
5
(b) State the class of alcohols to which compound P belongs and give the name of
compound R.
Class of alcohols ................................................................................................................
Name of R ..........................................................................................................................
(2 marks)
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(c) A simple chemical test can be used to distinguish between separate samples of R and S.
Suggest a suitable test reagent and state what you would observe in each case.
Test reagent ........................................................................................................................
Observation with R ............................................................................................................
Observation with S ............................................................................................................
(3 marks)
5
(d)
(i) Draw the structure of T.
(1 mark)
5
(d)
(ii) State the type of reaction that occurs in the conversion of S into T.
...................................................................................................................................
(1 mark)
10
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SECTION B
Answer each question in the space provided.
6 Consider the following reaction sequence.
CH3 CH3
CH3
C
C
Br
Br
CH3 CH3
Reaction 1
CH3
CH3
KOH(ethanol)
C
C
CH2
Br
Reaction 2
CH3 CH3
CH3
C
C
H
H
CH3 CH3
Reaction 3
CH3
H2C
C
C
CH2
Outline a mechanism for the elimination reaction shown in Reaction 1.
Give a reagent and catalyst for Reaction 3.
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(5 marks)
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7 Ethanol can be manufactured by two different processes. One process uses ethene and the
other uses glucose.
Process 1
H2C
CH2
+
H2O
CH3CH2OH
ethene
Process 2
C6H12O6
2CH3CH2OH
+
2CO2
glucose
For each process, name the type of reaction and give a suitable catalyst.
Give one advantage that each process has over the other.
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(6 marks)
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8 Write an equation for the reaction in which epoxyethane is manufactured on an industrial
scale. Identify the catalyst used and show clearly the structure of epoxyethane.
Write an equation for the reaction of one molecule of epoxyethane with one molecule of
water.
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(4 marks)
4
END OF QUESTIONS
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General Certificate of Education
June 2009
Advanced Subsidiary Examination
CHEMISTRY
Unit 3(a) Introduction to Organic Chemistry
CHM3/W
Gas constant R = 8.31 J K–1 mol–1
Table 1
Proton n.m.r. chemical shift data
Type of proton
δ/ppm
RCH3
0.7–1.2
R2CH2
1.2–1.4
R3CH
1.4–1.6
RCOCH3
2.1–2.6
ROCH3
3.1–3.9
RCOOCH3
3.7–4.1
ROH
0.5–5.0
Table 2
Infra-red absorption data
Insert to APW/Jun09/CHM3/W
Bond
Wavenumber/cm–1
C—H
2850–3300
C—C
750–1100
C
C
1620–1680
C
O
1680–1750
C—O
1000–1300
O—H (alcohols)
3230–3550
O—H (acids)
2500–3000
Insert to APW/Jun09/CHM3/W
H
*
89
† 90 – 103 Actinides
†
Actinium
Ac
227
57
Lanthanum
La
138.9
39
Yttrium
Y
88.9
21
Scandium
Sc
45.0
Lanthanides
88
* 58 – 71
87
Ra
Radium
Fr
223.0
Francium
56
226.0
55
Ba
Barium
132.9
Cs
38
137.3
37
Caesium
Sr
Strontium
Rb
85.5
Rubidium
20
87.6
19
Ca
Calcium
K
40.1
39.1
Potassium
12
11
Mg
Magnesium
Na
23.0
Sodium
4
24.3
3
Be
Beryllium
Li
9.0
II
72
Hafnium
Hf
178.5
40
Zirconium
Zr
91.2
22
Titanium
Ti
47.9
24
25
Tc
98.9
26
Ru
101.1
Iron
Fe
55.8
43
44
45
Sm
150.4
77
Iridium
Ir
192.2
46
Eu
152.0
78
Platinum
Pt
195.1
Protactinium
Th
Thorium
91
Pa
59
231.0
92
Uranium
U
238.0
60
93
Neptunium
Np
237.0
61
94
Plutonium
Pu
239.1
62
95
Americium
Am
243.1
63
Pm
144.9
76
Osmium
Os
190.2
Palladium
Pd
106.4
28
Nickel
Ni
58.7
Europium
Nd
144.2
75
Rhenium
Re
186.2
Rhodium
Rh
102.9
27
Cobalt
Co
58.9
Praseodymium Neodymium Promethium Samarium
Pr
140.9
74
Tungsten
W
183.9
42
Molybdenum Technetium Ruthenium
Mo
95.9
58
90
Mn
54.9
3
Li
Lithium
6.9
Chromium Manganese
Cr
52.0
232.0
Cerium
Ce
140.1
73
Tantalum
Ta
180.9
41
Niobium
Nb
92.9
23
Vanadium
V
50.9
atomic number
relative atomic mass
Key
47
96
Curium
Cm
247.1
64
Gadolinium
Gd
157.3
79
Gold
Au
197.0
Silver
Ag
107.9
29
Copper
Cu
63.5
30
Al
Cf
252.1
66
Dysprosium
Dy
162.5
81
Thallium
Tl
204.4
49
Indium
In
114.8
31
Gallium
Ga
13
69.7
Aluminium
6
50
Es
(252)
67
Holmium
Ho
164.9
82
Lead
Pb
207.2
Tin
Sn
118.7
32
Germanium
Ge
14
72.6
Silicon
Si
28.1
Carbon
C
12.0
IV
97
98
99
Berkelium Californium Einsteinium
Bk
247.1
65
Terbium
Tb
158.9
80
Mercury
Hg
200.6
48
Cadmium
Cd
112.4
Zinc
Zn
65.4
5
27.0
Boron
B
10.8
III
7
100
Fermium
Fm
(257)
68
Erbium
Er
167.3
83
Bismuth
Bi
209.0
51
Antimony
Sb
121.8
33
Arsenic
As
15
74.9
Phosphorus
P
31.0
Nitrogen
N
14.0
V
The atomic numbers and approximate relative atomic masses shown in the table are for use in the examination unless stated
otherwise in an individual question.
Lithium
1
6.9
Hydrogen
1.0
I
■
The Periodic Table of the Elements
8
101
Mendelevium
Md
(258)
69
Thulium
Tm
168.9
84
Polonium
Po
210.0
52
Tellurium
Te
127.6
34
Selenium
Se
16
79.0
Sulphur
S
32.1
Oxygen
O
16.0
VI
9
102
Nobelium
No
(259)
70
Ytterbium
Yb
173.0
85
Astatine
At
210.0
53
Iodine
I
126.9
35
Bromine
Br
17
79.9
Chlorine
Cl
35.5
Fluorine
F
19.0
VII
He
10
103
Lawrencium
Lr
(260)
71
Lutetium
Lu
175.0
86
Radon
Rn
222.0
54
Xenon
Xe
131.3
36
Krypton
Kr
18
83.8
Argon
Ar
39.9
Neon
Ne
2
20.2
Helium
4.0
0