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General Certificate of Education

June 2009
Advanced Subsidiary Examination

CHEMISTRY CHM3/W
Unit 3(a) Introduction to Organic Chemistry

Wednesday 3 June 2009 9.00 am to 10.00 am

For this paper you must have For Examiner’s Use

● the Periodic Table/Data Sheet provided as an

insert (enclosed) Question Mark Question Mark

● a calculator.

Time allowed: 1 hour 2

Instructions 3
● Use black ink or black ball-point pen.
4
● Fill in the boxes at the top of this page.

● Answer all questions. 5

● Answer the questions in Section A and Section B in the spaces

provided. Answers written in margins or on blank pages will not 6

be marked.
● Your answers to Section B should be on the pages indicated. 7
● All working must be shown.

● Do all rough work in this book. Cross through any work you do not
8
want to be marked.
Total (Column 1) →
● The Periodic Table/Data Sheet is provided as an insert.

Total (Column 2) →
Information
● The maximum mark for this paper is 60. TOTAL
● The marks for questions are shown in brackets.

● You are expected to use a calculator where appropriate. Examiner’s Initials

● 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.

Advice
● You are advised to spend about 45 minutes on Section A and about

15 minutes on Section B.

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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 .................................................................................................................

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(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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1 (c) (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.

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(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.

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(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)

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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 C3HF7 + …… HF (1 mark)

3 (b) (ii) Draw the structure of one of the possible isomers of C3HF7

(1 mark)

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3 (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.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................
(3 marks)

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4 The table shows five structural isomers.

Structure Name
Isomer 1
CH2
H2C CH2
H2C CH2
CH2

Isomer 2
H
CH3CH2CH2 C C CH3 hex-2-ene
H

Isomer 3
CH3
CH3CH2CH2 C C H 2-methylpent-1-ene
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. (2 marks)

4 (b) State what is meant by the term structural isomers.

.............................................................................................................................................

.............................................................................................................................................

.............................................................................................................................................
(2 marks)

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4 (c) (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.

O
KOH(aq) K2Cr2O7/H2SO4
CH3CHBrCH3 CH3CH(OH)CH3 CH3 C CH3

2-bromopropane P R

O
KOH(aq) K2Cr2O7/H2SO4
CH3CH2CH2Br CH3CH2CH2OH CH3CH2 C H

1-bromopropane Q 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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5 (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 CH3

Reaction 1
CH3 C C CH3 CH3 C C CH2
KOH(ethanol)
Br Br Br

Reaction 2

CH3 CH3 CH3 CH3

Reaction 3
CH3 C C CH3 H2C C C CH2
H H

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.

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................

......................................................................................................................................................
(4 marks)

END OF QUESTIONS

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APW/Jun09/CHM3/W
General Certificate of Education
June 2009
Advanced Subsidiary Examination

CHEMISTRY CHM3/W
Unit 3(a) Introduction to Organic Chemistry

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

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
 The Periodic Table of the Elements
■ 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.

I II III IV V VI VII 0

Insert to APW/Jun09/CHM3/W
1.0 4.0
H He
Hydrogen
Key Helium
1 2
6.9 9.0 relative atomic mass 6.9 10.8 12.0 14.0 16.0 19.0 20.2
Li Be Li B C N O F Ne
Lithium Beryllium Lithium Boron Carbon Nitrogen Oxygen Fluorine Neon
3 4 atomic number 3 5 6 7 8 9 10
23.0 24.3 27.0 28.1 31.0 32.1 35.5 39.9
Na Mg Al Si P S Cl Ar
Sodium Magnesium Aluminium Silicon Phosphorus Sulphur Chlorine Argon
11 12 13 14 15 16 17 18
39.1 40.1 45.0 47.9 50.9 52.0 54.9 55.8 58.9 58.7 63.5 65.4 69.7 72.6 74.9 79.0 79.9 83.8
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
85.5 87.6 88.9 91.2 92.9 95.9 98.9 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
Rubidium Strontium Yttrium Zirconium Niobium Molybdenum Technetium Ruthenium Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
132.9 137.3 138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 210.0 210.0 222.0
Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
Caesium Barium Lanthanum Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
*
223.0 226.0 227
Fr Ra Ac
Francium Radium Actinium
87 88 89 †

140.1 140.9 144.2 144.9 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
* 58 – 71 Lanthanides Cerium Praseodymium Neodymium Promethium Samarium Europium Gadolinium Terbium Dysprosium Holmium Erbium Thulium Ytterbium Lutetium
58 59 60 61 62 63 64 65 66 67 68 69 70 71
232.0 231.0 238.0 237.0 239.1 243.1 247.1 247.1 252.1 (252) (257) (258) (259) (260)
Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
† 90 – 103 Actinides Thorium Protactinium Uranium Neptunium Plutonium Americium Curium Berkelium Californium Einsteinium Fermium Mendelevium Nobelium Lawrencium
90 91 92 93 94 95 96 97 98 99 100 101 102 103