Hydrocarbons

Worksheet#13 As Hydrocarbons
CHEMISTRY
AS
WORKSHEET#13
HydroCarbons
COMPILED BY:
KAMRAN SHAHZAD
 Cell#0314 538 9234
 E-mail:shahzadkamran@hotmail.com
KAMRAN SHAHZAD 1
Q1. Cottonseed oil contains large amounts of polyunsaturated carboxylic acids. When this oil is
used to make margarine, the C-C double bonds in the unsaturated carboxylic acids are
hydrogenated.
What reagents and conditions would be suitable to bring about this hydrogenation reaction?
A. H2 gas, nickel catalyst, 400oC

B. LiAlH4 in dry ether
C. NaBH4, aqueous solution
D. Steam, concentrated H2SO4, 300oC and 60 atm pressure
M/J-15-11
Q2. Which intermediate ion forms in the greatest amount during the addition of HBr to
propene?
A. CH3CH+CH3
B. CH3CH2CH2+
C. CH3CH-CH2Br
D. CH3CHBrCH2-
M/J-15-11
Q3. In 1869 Ladenburg suggested a structure for benzene, C6H6, in which one hydrogen atom is
attached to each carbon atom.
A compound C6H4Cl2 could be formed with the same carbon skeleton as the Ladenburg
structure. How many structural isomers would this compound have?
A. 3 B. 4 C. 5 D. 6
M/J-15-11
Q4. The citrus flavor of lemons is due to the compound limonene, present in both the peel and
the juice.
KAMRAN SHAHZAD 2
What is the mole ratio of carbon dioxide to water produced when limonene is completely
burnt in oxygen?
Number of moles Number of moles

carbon dioxide water
A 4 3
B 5 4
C 5 8
D 9 7
M/J-15-11
Q5. Four students, W, X, Y and Z made the following statements about alkanes and alkenes.
W ‘Bromine reacts with alkanes by electrophilic substitution.’
X ‘Bromine reacts with alkenes by a free-radical addition mechanism.’
Y ‘Alkenes can be oxidised by acidified manganite (VII) ions.’
Z ‘Alkenes are formed from alkanes by cracking.’
Which two students are correct?
A. W and X B. W and Z C. X and Y D. Y and Z

M/J-15-12
Q6. Aluminium carbide, Al4C3, reacts readily with aqueous sodium hydroxide. The two products
of the reaction are NaAlO2 and a hydrocarbon. Water molecules are also involved as
reactants.
What is the formula of the hydrocarbon?
A. CH4 B. C2 H 5 C. C3 H 8 D. C6H12
O/N-14-12
Q7. Which row correctly describes the reaction between propene and bromine, Br 2(l)?
Reaction mechanism Organic product

A Electrophilic addition CH3CHBrCH2Br
B Electrophilic addition CH3CH2CH2Br
C Nucleophilic substitution CH3CH2CH2Br
D Nucleophilic substitution CH3CHBrCH2Br
O/N-14-12
KAMRAN SHAHZAD 3
Q8. Which compound as an Mr of 84 and will react with HBr to give a product with an Mr of
164.9?
O/N-14-12
Q9.Corticosterone is a hormone involved in the metabolism of carbohydrates and proteins.
How many chiral centres are there in one molecule of corticosterone?
A. 5 B. 6 C. 7 D. 8
O/N-14-12
Q10. Which equation correctly represents the balanced equation for the complete combustion of
a hydrocarbons with the formula CxHy?
( 2y )O
A. CxHy + x + 2 xCO2 +
y
HO
2 2
B. C H + ( x + )O
y
x y 2 xCO2 + y H 2O
4
C. C H + ( x + )O
y y
x y 2 xCO2 + HO
4 4 2
D. C H + ( x + )O
y y
x y 2 xCO2 + H2O
4 2
O/N-14-12
KAMRAN SHAHZAD 4
Q11. Methyl methylpropenoate is the monomer used to make Perspex.
Which diagram correctly shows methyl methylpropenoate?
O/N-14-12
Q12. In this question, structural isomerism and stereoisomerism should be considered.
How many isomeric aldehydes have the formula C5H10O?
A. 3 B. 4 C. 5 D. 6
O/N-14-13
Q13. The compound known as ‘gamma-linolenic acid’ is found in the seeds of the evening
primrose plant.
CH3(CH2)4CH=CHCH2CH=CHCH2CH=CH(CH2)4CO2H
Gamma-linolenic acid
How many cis-trans isomers are there with this structural formula?
A. 3 B. 6 C. 8 D. 12
O/N-14-13
Q14. β-carotene is responsible for the orange colour of carrots.
β-carotene is oxidised by hot, concentrated, acidified KMnO4.
KAMRAN SHAHZAD 5
When an individual molecule of β-carotene is oxidised in this way, many product molecules
are formed.
How many of these product molecules contain a ketone functional group?
A. 4 B. 6 C. 9 D. 11
O/N-14-12
Q15. Methyl butanoate, C5H10O2, is an ester used in the food industry to give products the flavor
of apples.
Including methyl butanoate, how many structural isomers are there of C 5H10O2 that are
esters?
A. 6 B. 8 C. 9 D. 10
O/N-14-13
Q16. The diagram shows the structure of the naturally-occurring molecule cholesterol.
Student X stated that the seventeen carbon atoms in the four rings all lie in the same plane.
Students Y stated that this molecule displays cis-trans isomerism at the C = C double bond.
Which of the students are correct?
A. Both X and Y
B. Neither X nor Y
C. X only
D. Y only
O/N-14-13
KAMRAN SHAHZAD 6
Q17. Poly (ethanol) can be used to make plastic bags that dissolve in water.
It may be considered to be made by addition polymerization of CH2 = CH(OH).
Which structure represents a length of the polymer chain consisting of two monomer
residues?
O/N-14-13
Q18. The diagram shows the skeletal formula of phenazine.
What is the empirical formula of phenazine?
A. C6H4N B. C6 H 6 N C. C12H8N2D. C12H12N2
M/J-14-12
Q19. Which alcohol has a chiral centre and can be oxidised to a ketone?
A. Pentan-2 –ol
B. Pentan-3-o
C. 3-methylhexan-1 -ol
D. 3-methylhexan-3 –ol
M/J-14-12
KAMRAN SHAHZAD 7
Q20. Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH.
Which statement about these products is correct?
A. Both products are obtained in this reaction by electrophilic substitution.
B. Both products are obtained in this reaction by nucleophilic addition.
C. Both products can be hydrolysed to form the same organic compound.
D. Both products can form hydrogen bonds with water.
M/J-14-12
Q21. Which statement does not correctly describe a problem related to the disposal of PVC?
A. PVC is slowly degraded in the environment by bacteria and fungi.
B. PVC is slowly degraded in environment by sunlight.
C. When PVC is burnt, a significant amount of ethane gas is present in the products.
D. When PVC is burnt, a significant amount of HCl gas is present in the products.
M/J-14-12
Q22. Artermisinin is a powerful anti-malarial drug.
How many chiral centres are there in each molecule of artemisinin?

A. 4 B. 6 C. 7. D. 8
M/J-14-12
Q23. Which stage in the free radical substitution of methane by chlorine will have the lowest
activation energy?
KAMRAN SHAHZAD 8
O/N-13-12
Q24. The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass.
CH3CH2CH=CHCH2CH2OH
Leaf alcohol
What will be formed when ‘leaf alcohol’ is oxidised using an excess of hot, acidified
K2Cr2O7(aq)?
A. CH3CH2CH(OH)CH2CO2H
B. CH3CH2COCOCH2CO2H
C. CH3CH2CH=CHCH2CO2H
D. CH3CH2CO2H and HO2CCH2CO2H
O/N-13-12
Q25. Which compound exhibits stereoisomerism?
A. CH3CHClCH3
B. CH3CHClCH2Cl
C. CH3CCl2CH3
D. CH2ClCH2CH2Cl
O/N/13-12
Q26. Which types of bond breakage and bond formation occur in the addition polymerisation of
alkenes?
O/N-13-12
Q27. Which stage in the free radical substitution of ethane by chlorine will have the lowest
activation energy?
KAMRAN SHAHZAD 9
O/N-13/13
Q28. Including structural and stereoisomers, how many isomers are there of C 2H2Br2?
A. 2 B. 3 C. 4 D. 5
O/N-13-13
Q29. Pent-2-ene, CH3CH2CH = CHCH3, reacts in a similar way to ethane.
Pent-2-ene is reacted with cold, dilute, acidified manganite (VII) ions.
What will be produced in the greatest amount?
A. CH3CH2CH(OH)CH(OH)CH3
B. CH3CH2COCOCH3
C. A mixture of CH3CH2CH(OH)CH2CH3 and CH3CH2CH2CH(OH)CH3
D. CH3CH2COOH and CH3COOH
O/N-13-13
Q30. Which fragment could appear in the chain produced by polymerizing 1, 1 –dichloroethene?
A. –CH2-CH2-CCl2-CCl2-CH2-CH2-
B. –CHCl-CHCl-CHCl-CHCl-CHCl-CHCl-
C. –CH2-CCl2-CH2-CH2-CH2-CCl2-
D. –CCl2-CCl2-CH2-CH2-CH2-CCL2-
O/N-13-13
Q31. The following compounds are found in the seaweed Asparagopsis taxiformis.
Which compound could show both cis-trans isomerism and optical isomerism?
M/J-13-11
Q32. Pentane, C5H12, is reacted with chlorine in the presence of ultraviolet light. A compound R is
found in the products. R has molecular formula C5H10Cl2. Each molecule of R contains one
chiral carbon atom.
Which two atoms of the pentane chain could be bonded to chlorine atoms in this isomer?
KAMRAN SHAHZAD 10
A.1 and 3 B. 1 and 5 C. 2 and 3 D. 2 and 4
M/J-13-11
Q33. Synthetic resins, plasticisers and many other chemicals can be made by polymerization of a
variety of monomers including prop-2-en-1-ol, CH2 = CHCH2OH.
Which structure represents the repeat unit in poly (prop-2-en-1 –ol)?
M/J-13-11
Q34. Bromine reacts with ethane to form 1, 2 –dibromoethane.
What is the correct description of the organic intermediate in this reaction?
A. It has a negative change

B. It is a free radical
C. It is a nucleophile
D. It is an electrophile
M/J-13-11
Q35. Some vegetable oils contain ‘trans fats’ that are associated with undesirable increases in the
amount of cholesterol in the blood.
In the diagrams below, R1 and R2 are different hydrocarbon chains.
Which diagram correctly illustrates an optically active ‘trans fat’?
KAMRAN SHAHZAD 11
M/J-13-11
Q36. Sorbic acid is used as a food preservative because it kills fungi and moulds.
Sorbic acid will react with
 Hydrogen in the presence of a nickel catalyst.

 Bromine in an organic solvent.
How many moles of hydrogen and of bromine will in incorporated into one mole of sorbic
acid by these reactions.
moles of hydrogen moles of bromine

A 2 2
1
B 2 2
2
C 3 2
1
D 3 2
2
M/J-13-12
Q37. When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitutions.
In a propagation step a free radical is formed
How many different forms of are possible?
A. 1 B. 2 C. 3 D. 4
M/J-13-12
KAMRAN SHAHZAD 12
Q38. Polymerisation of ethane gives poly (ethane).
How does the carbon-carbon bond in poly (ethane) compare with that in ethane?
A. The carbon-carbon bond is longer and stronger in poly (ethane).

B. The carbon-carbon bond is longer and weaker in poly (ethane).
C. The carbon-carbon bond is shorter and stronger in poly (ethane).
D. The carbon-carbon bond is shorter and weaker in poly (ethane).
M/J-13-12
Q39. Carvone is found in spearmint.
How many σ and π bonds are present in this molecule?
σ π
A 13 3
B 22 3
C 22 6
D 25 3
O/N-12-12
Q40. An alkene has the formula CH3CH = CRCH2CH3 and does not possess cis-trans isomers.
What is R?
A. H B. Cl C. CH3 D. C2 H 5
O/N-12-12
Q41. Menthol is an important compound extracted from the peppermint plant.
KAMRAN SHAHZAD 13
How many chiral center are there in one molecule of menthol?
A. 1 B. 2 C. 3 D. 4
O/N-12-12
Q42. But-2-ene- 1, 4-diol is converted in two steps through an intermediate X into

ketobutanedioic acid.
What could be the reagent for step 1 and the intermediate X?
reagent for step 1 X
A cold acidified KMnO4 OHCH2CH2CH(OH)CH2OH
B hot acidified KMnO4 OHCCH(OH)CH2CHO

steam and concentrated
C HOCH2(OH)CH2CH2OH
H2SO4
D warm acidified K2Cr2O7 HO2CCH=CHCO2H
O/N-12-12
Q43. The cracking of a single hydrocarbon molecule, CnH2n+2, produces two hydrocarbon molecules
only. Each hydrocarbon product contains the same number of carbon atoms in one
molecule. Each hydrocarbon product has non-cyclic structural isomers.
What is the value of n?
A. 4 B. 6 C. 8 D. 9
O/N-12-12
Q44. High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes,

commonly known as CFCs.
Which free-radical is most likely to result from the irradiation of CHFClCF2Cl?
KAMRAN SHAHZAD 14
O/N-12-12
Q45. Isomers X and Y both react with HBr.
A mixture of X and Y is reacted with HBr.
Which three structures represent three different possible products of this reaction?
A. (CH3)2CHCBr3 (CH3)2CBrCHBr2 CH3CHBrCHBrCH3

B. (CH3)2CHCBr3 (CH3)2CBrCHBr2 CH3CBr2CHBrCH3
C. (CH3)2CBrCBr3 (CH3)2CHCBr3 CH3CBr2CHBrCH3
D. (CH3)2CBrCHBr2 CHBr2CBr(CH2)CH3 CH3CHBrCBr2CH3
M/J-12-12
Q46. Oct-1-ene, CH3(CH2)5CH = CH2, is subjected to thermal cracking.
Which combination of compounds W, X, Y and Z can be obtained?
CH2 = CH2 CH3CH = CH2 CH3CH2CH3 CH2 = CHCH = CH2
W X Y Z
A. W, X, Y and Z
B. W, X and Y only
C. W, X and Z only
D. W and X only
M/J-12-12
Q47. Bromine and propene undergo an addition reaction.
Which is a property of the product?
A. It exists in cis-trans isomers.
B. It is more volatile than propene.
KAMRAN SHAHZAD 15
C. It possesses a chiral centre.
D. It possesses hydrogen bonding.
O/N-11-12
Q48. Use of the Data Booklet is relevant to this equation.
Which bond in the structure below has the lowest bond energy?
O/N-11-12
Q49. The molecule shown in optically active.
How many chiral carbon atoms are present in this molecule?
A. 1 B. 2 C. 3 D. 4
O/N-11-12
Q50. In the general formula of which class of compound, is the ratio of hydrogen atoms to carbon
atoms the highest?
A. Alcohols
B. Aldehydes
C. Carboxylic acids
D. Halogenoalkanes
O/N-11-13
Q51. An unpleasant smelling chemical produced in the human armpit is 3-methylhex-2-enoic acid.
KAMRAN SHAHZAD 16
If this compound is reacted with a cold, dilute, acidified solution of potassium

manganite (VII), how many chiral centres will be produced?
A. 0 B. 1 C. 2 D. 3
O/N-11-13
Q52. Energy is released in the human body by the oxidation of glucose in a complex sequence of
reactions. Part of this sequence is the Krebs cycle. One reaction in the Krebs cycle is the
conversion of fumaric acid into malic acid.
Which reagents could achieve this transformation in the laboratory?

A. Acidified KMnO4
B. Br2(aq) followed by hot NaOH(aq)
C. H2O with Pt catalyst
D. Steam with H2SO4
O/N-11-13
Q53. A reaction between chlorine and propane in ultraviolet light produces two isomeric
monochloropropanes, C3H7Cl, as products.
Which information about this reaction is correct?
O/N-11-13
Q54. The products obtained by cracking an alkane, X, are methane, ethane and propene.
The mole fraction of ethane in the products is 0.5.
What is the identity of X?
KAMRAN SHAHZAD 17
A. C6H14 B. C8H18 C. C9H20 D. C11H24
M/J-11-12
Q55. Which compound does not show cis-trans isomerism?
A. 2-methylplent-2-ene
B. 3-methylpent-2-ene
C. 3,4-dimethylhex-3-ene
D. Pent-2-ene
M/J-11-12
Q56. How many isomers with the formula C5H10 have structures that involve π bonding?
A. 3 B. 4 C. 5 D. 6
M/J-11-12
Q57. This question should be answered by considering the reactions of KMnO4 with different
functional groups under the stated conditions.
The diagram shows the structure of the naturally-occurring molecule cholesterol.
Cholesterol is separately treated with
 Cold, dilute acidified KMnO4,

 Hot, concentrated acidified KMnO4.
What is the change in the number of chiral carbon atoms in the molecule during each
reaction?
KAMRAN SHAHZAD 18
M/J-11-12
Q58. One of the characteristics of addition polymerization is that the empirical formulae of the
polymer and of its monomer are the same. The absorbent material in babies’ disposable
nappies is made from the addition polymer shown.
From which monomer could this addition polymer be obtained?
A. CH3CH(OH)CO2H
B. HOCH2CH2CO2H
C. H2C=CHCO2H
D. H2OCCH=CHCO2H
O/N-10-11
Q59. Limonene is an oil formed in the peel of citrus fruits.
Which product is formed when an excess of bromine, Br2(I), reacts with limonene at room
temperature in the dark?
KAMRAN SHAHZAD 19
O/N-10-11
Q60. The compound 2-methylpropene, C4H8, is a monomer used in the production of synthetic
rubber.
In addition to 2-methylpropene there are x other isomers of C4H8, structural or otherwise,

which contain a double bond.
What is the value of x?
A. 1 B. 2 C. 3 D. 4
O/N-10-11
Q61. When gaseous chemicals are transported by road or by rail they are classified as follows.
Flammable non-flammable poisonous
Which commonly transported gas is non-flammable?
A. Butane
B. Hydrogen
C. Oxygen
D. Propene
M/J-10-12
substitution.
In a propagation step the free radical Xois formed.
KAMRAN SHAHZAD 20
How many different forms of Xo are possible?
A. 1 B. 2 C. 3 D. 4
M/J-10-12
Q63. Which compound exhibits both cis-trans ad optical isomerism?
A. CH3CH=CHCH2CH3
B. CH3CHBrCH=CH2
C. CH3CBr=CBrCH3
D. CH3CH2CHBrCH=CHBr
M/J-10-12
Q64. Polymerisation of 1, 1-dichloroethene produces a dense, high melting point substance that
does not allow gases to pass through. It is used as cling wrapping.
Which sequence appears in a short length of the polymer chain?
M/J-10-12
Q65. The drug cortisone has the formula shown.
In addition to those chiral centres marked by an asterisk (*), how many other chiral centres
are present in the cortisone molecule?
A. 0 B. 1 C. 2 D. 3
O/N-09-12
KAMRAN SHAHZAD 21
Q66. What is the least number of carbon atoms in a non-cyclic alkane molecule that has a chiral
centre?
A. 7 B. 8 C. 9 D. 10
O/N-09-12
Q67. The following diagram represents the structure of a possible polymer.
By which method might this polymer be made?
A. Polymerise ethane followed by hydration

B. Polymerise ethane followed by oxidation with cold acidified KMnO4
C. Polymerise 1, 2-dichloroethene followed by hydrolysis
D. Polymerise 1,2-dichloroethene followed by oxidation with cold acidified KMnO 4
O/N-09-12
Q68. Sorbic acid is used as a food preservative because it kills fungi and moulds.
Sorbic acid will react with

 Hydrogen in the presence of a nickel catalyst,
 Bromine in an organic solvent.
How many moles of hydrogen and of bromine will be incorporated into ne mole of sorbic
acid by these reactions?
KAMRAN SHAHZAD 22
O/N-09-12
Q69. Which equation represents a valid propagation step in the free radical reaction between
ethane and chlorine?
O/N-09-12
Q70. Which statement explains why the boiling point of methane is higher than that of neon?
[Ar: H, 1 ; C, 12 ; Ne, 20]
A. A molecule of methane has a greater mass than a molecule of neon.

B. Molecules of methane form hydrogen bonds, but those of neon do not.
C. Molecules of methane have stronger intermolecular forces than those of neon.
D. The molecule of methane is polar, but that of neon is not.
M/J-09-01
Q71. In recent years a number of athletes have been banned from sports because of their illegal
use of synthetic testosterone, a naturally occurring hormone in the body.
How many chiral centres are present in a testosterone molecule?
A. 1. B. 2 C. 3 D. 6
M/J-09-01
KAMRAN SHAHZAD 23
Q72. The compound known as ‘gamma-linolenic acid’ is found in significant amounts in the speed
of the Evening Primrose plant. There is evidence that the compound may help patients with
diabetes.
How many cis-trans isomers does gamma-linolenic acid have?
A. 3 B. 6 C.8 D. 12
M/J-09-01
Q73. What always applies to a nucleophile?
A. It attacks a double bond.

B. It has a lone pair of electrons.
C. It is a single atom.
D. It is negatively charges.
M/J-09-01
Q74. Trichloroethanoic acid, CCl3CO2H, is used in cosmetic surgery to perform a ‘chemical peel’ to
remove dead skin.
Trichloroethanoic ACID can be made by reacting chlorine with ethanoic acid.
What is the mechanism of this reaction?
A. Electrophilic addition
B. Electrophilic substitution
C. Free radical addition
D. Free radical substitution
M/J-09-01
Q75. Polymerisation of chloroethene gives PVC.
How does the carbon-carbon bond n PVC compare with that in chloroethene?
A. Longer and stronger
B. Longer and weaker
C. Shorter and stronger
D. Shorter and weaker
M/J-09-01
Q76. 2-Methylbuta- 1, 3-diene, CH2=C(CH3)-CH=CH2, is used as a monomer in the manufacture of
synthetic rubbers.
KAMRAN SHAHZAD 24
Which compound would not produce this monomer on treatment with concentrated sulfuric
at 170oC?
A. (CH3)2C(OH)CH(OH)CH3
B. HOCH2CH(CH3)CH2CH2OH
C. HOCH2CH(CH3)CH(OH)CH3
D. HOCH2C(CH3)(OH)CH2CH3
M/J-09-01
Q77. Sorbitol is a naturally-occurring compound with a sweet taste. It is often used as a substitute
for sucrose by the food industry.
The diagram shows its structure.
How many chiral centres are present in sorbitol?
A. 1 B. 2 C. 3 D. 4
O/N-08-01
Q78. The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass.
Which two compounds will be formed when ‘leaf alcohol’ is oxidised using hot, concentrated
manganite (VII) ions?
A. CH3CO2H and HOCH2CH2CH2CO2H

B. CH3CO2H and HO2CCH2CH2CO2H
C. CH3CH2CO2H and HO2CCH2CO2H
D. CH3CH2CO2H and HOCH2CH2CO2H
O/N-08-01
KAMRAN SHAHZAD 25
Q79. Which hydrocarbon can form a monochloro-substitution derivative which shows both
chirality and cis-trans isomerism?
A. CH3CH=CH2
B. (CH3)2C=CH2
C. CH3CH=C(CH3)2
D. CH3CH=CHCH2CH3
O/N-08-01
Q80. Trichloroethene is widely used as a dry-cleaning agent.
With which of the following does trichloroethene react to give a chiral product?
A. Br2 B. HCl C. NaCN(aq) D. NaOH(aq)

M/J-08-01
Q81. Chloroethene, CH2=CHCl, is the monomer of PVC.
What are the C-C-C bond angles along the polymeric chain in PVC?
A. They are all 109.5o.

B. Half are 109.5o and half are 120o.
C. They are all 120o.
D. They are all 180o.
M/J-08-01
Q82. Which hydrocarbon would not be collected in the inverted tube by heating pentane,
CH3(CH2)3CH3, in the apparatus shown?
KAMRAN SHAHZAD 26
A. CH4
B. CH3CH3
C. CH3CH2CH=CH2
D. CH3(CH2)8CH3
M/J-08-01
Q83. Which molecules, each with a linear carbon chain, can have an optically active isomer?
A. I and II only
B. I, II and III only
C. II and III only
D. I, II and IV only
O/N-07-01
Q84. In which pair do the isomers have identical boiling points?
KAMRAN SHAHZAD 27
O/N-07-01
Q85. Tetramethyl-lead (IV), (CH3)4Pb, increases the rate of the reaction of methane with chlorine.
Why can tetramethyl-lead (IV) behave in this way?
A. It is a source of methyl radicals.
B. It releases .
C. It reacts with chloromethane and prevents equilibrium being established.
D. Metal ions catalyse the reaction.
O/N-07-01
Q86. Which reaction occurs when ethane and chlorine are mixed in diffused sunlight?
A. A free-radical substitution with hydrogen given off.

B. A free-radical substitution with hydrogen chloride given off.
C. A free-radical substitution with no gas given off.
D. A nucleophilic substitution with hydrogen chloride given off.
O/N-07-01
Q87. Limonene is oil formed in the peel of citrus fruits.
Which product is formed when molecular bromine reacts with limonene at room
temperature in the dark?
KAMRAN SHAHZAD 28
O/N-07-01
Q88. The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below.
Which type of reaction is occurring in stage 2?
C. Free radical substitution
D. Nucleophilic addition
O/N-07-01
Q89. Glucose, C6H12O6, is a product of photosynthesis.
It has the following structure.
How many chiral centres does the molecule have?
KAMRAN SHAHZAD 29
A. 1. B. 2 C. 4 D. 6
M/J-07-01
Q90. Which reagent could be used to convert CH3CO2CH3 into ClCH2CO2CH3?
A. Concentrated hydrochloric acid at 100oC.

B. Phosphorus pentachloride at room temperature.
C. Sulphur dichloride oxide (thionyl chloride, SOCl2) at 50 oC.
D. Chlorine in bright sunlight at 100 oC.
M/J-07-01
Q91. In which class of compound, in its general formula, is the ratio of hydrogen atoms to carbon
atoms the highest?
A. Alcohols
B. Aldehydes
C. Carboxylic acids
D. Halogenoalkanes
O/N-06-01
Q92. What isthe total number of different chloroethanes, formula C2H6-nCln, where n can be any
integer from 1 to 4?
A. 4 B. 6 C. 7 D. 8
O/N-06-01
Q93. Which alkene could exist in cis and trans forms?
KAMRAN SHAHZAD 30
O/N-06-01
Q94. When gaseous chemicals are transported by road or by rail they are classified as follows.
Flammable non-flammable poisonous
Which gas is non-flammable?
A. Butane
B. Hydrogen
C. Oxygen
D. Propene
O/N-06-01
Q95. Which equation or statement describes what happens when poly 9propene) is burned in an
excess of air?
O/N-06-01
Q96. Warfarin is used as a rat poison.
How many chiral centres ar present in the warfarin molecule?
A. 0 B. 1 C. 2 D. 3
M/J-06-01
Q97. The structures below show isomers of C6H12.
KAMRAN SHAHZAD 31
In which pair are the members cis-trans isomers of each other?
A. 1 and 2 B. 1 and 3 C. 1 and 4 D. 2 and 4

M/J-06-01
Q98. Light initiates the following reaction.
What happens to chlorine in this photochemical reaction?

A. Heterolytic fission to give an electrophile
B. Hemolytic fission to give an electrophile
C. Heterolytic fission to give a free radical
D. Homoltic fission to give a free radical
M/J-06-01
Q99. High-energy irradiation in the stratosphere produces radicals from chlorofluoroalkanes,
commonly known as CFCs.
Which radical could result from this irradiation of CHFClCF2Cl?
M/J-06-01
Q100. The diagram shows the structure of vitamin C.
How many chiral centres are there in one molecule?
A. 1 B. 2 C. 3 D. 4
KAMRAN SHAHZAD 32
O/N-05-01
Q101. In the upper atmosphere chlorofluoroalkanes (CFCs) are broken down to give chlorine
radicals but not fluorine radicals.
What is the best explanation for this?
A. Fluorine is more electronegative than chlorine.
B. Fluorine radicals are less stable than chlorine radicals.
C. The C-F bond is stronger than the C-Cl bond.
D. The chlorine atom is larger than the fluorine atoms.
O/N-05-01
Q102. Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give
ethanoic acid only?
O/N-05-01
Q103. Under the Montreal Protocol the use of chlorofluorocarbons is to be phased out.
Fluorocarbons are often used to replace them. One chlorofluorocarbon which was widely
used as a solvent is CCl2FCClF2 and large stocks of it remain. One process to use up these
stocks is to convert it into the fluorocarbon CH2FCF3 by the following route.
What type of reaction is step 1?
A. Elimination
B. Free radical substitution
KAMRAN SHAHZAD 33
C. Isomerization
D. Nucleophilic substitution
M/J-05-01
Q104. When bromine reacts with propene in an organic solvent at room temperature, what is the
mechanism by which the bromine attacks the propene?
C. Nucleophilic addition
D. Nucleophilic substitution
M/J-05-01
Q105. Which of these compounds, on complete combustion of one mole, will release the greatest
amount of energy?
A. CH3CH2CH2OH
B. CH3CH2CH3
C. CH3CH2CO2H
D. CH3COCH3
O/N-04-01
Q106. This molecule is responsible for the flavor of spearmint chewing gum.
What is a true statement about the functional group X or Y?
A. X will undergo nucleophilic addition.

B. Y will undergo nucleophilic addition.
C. X will undergo electrophilic substitution.
D. Y will undergo electrophilic substitution.
O/N-04-01
KAMRAN SHAHZAD 34
Q107. Which reaction occurs with saturated hydrocarbons?
A. Catalytic hydrogenation
B. Ready decolourisation of aqueous bromine
C. Polymerization
D. Thermal cracking
O/N-05-01
Q108. How many different substitution products are possible, in principle, when a mixture of
bromine and ethane is allowed to react?
A. 3 B. 5 C. 7 D. 9
O/N-04-01
Q109. Which molecule does not have a chiral centre?
O/N-04-01
Q110. The reaction of chlorine with methane is carried out in the presence of light.
What is the function of the light?
A. To break the C – H bonds in methane

B. To break up the chlorine molecules into atoms
C. To break up the chlorine molecules into ions
D. To heat up the mixture
O/N-04-01
Q111. Which compound could not be obtained from cracking a sample of nonane, CH3(CH2)7CH3?
A. CH3CH = CHCH = CHCH2CH2CH2CH3
KAMRAN SHAHZAD 35
B. CH3CH2CH2CH2CH3
C. CH3CH2CH2CH2CH2CH = CH2
D. (CH3CH2CH2)3CH
M/J-04-01
Q112. Ethene reacts with aqueous bromine to give two products, CH2BrCH2Br and CH2BrCH2OH.
Which statement is correct for these products?
A. Both products are obtained in this reaction by electrophilic substitution.
B. Both products are obtained in this reaction by nucleophilic addition.
C. Both products can be hydrolysed to form the same diol.
D. Both products can form hydrogen bonds with water.
M/J-04-01
Q113. In which way are ethene and propane similar?
A. They are both obtained by the dehydration of alcohols.

B. They are neutral to an indicator solution.
C. They can both be hydrogenated using a suitable catalyst.
D. They can both undergo polymerization under suitable conditions.
M/J-04-01
Q114. How many alcohols (including both structural isomers and stereoisomers) can have the
molecular formula C4H10O?
A. 3 B. 4 C. 5 D. 6
O/N-03-01
Q115. Hydrogen bromide reacts with ethene to form bromoethane.
What is the best description of the organic intermediate in this reaction?
A. It contains carbon, hydrogen and bromine.
B. It has a negative charge.
C. It is an electrophile.
D. It is a free radical.
O/N-03-01
Q116. On strong heating a hydrocarbon produces ethene, propane and but-1-ene in the mole ratio
5 : 1 : 1.
KAMRAN SHAHZAD 36
What is the molecular formula of the hydrocarbon?
A. C17H34 B. C17H36 C. C19H38 D. C19H40
O/N-03-01
Q117. In the preparation of soft margarine, glyceryl trieleostearate.
is suitably hydrogenated so that, on average, one of its side-chains is converted into the
CH3(CH2)4CH = CHCH2CH = CH(CH2)7CO2 residue and two side-chains are converted into the
CH3(CH2)7CH = CH(CH2)7CO2 residue.
How many moles of hydrogen are required to convert on mole of glyceryl trieleostearate
into the soft margarine?
A. 4 B. 5 C. 6 D. 9
M/J-03-01
Q118. Cyclohexa-1,4-diene is treated with a solution of bromine in tetrachloromethane.
Which product is formed?
KAMRAN SHAHZAD 37
M/J-03-01
Q119. Chlorofluoroalkanes, commonly known as CFCs, undergo hemolytic fission by ultraviolet
irradiation in the stratosphere.
Which radical could result from this irradiation of CHFClCF2Cl?
M/J-03-01
Q120. The complete combustion of alkanes to produce carbon dioxide and water is an important
exothermic reaction.
Which line on the graph shows the relationship between the number of carbon atoms in the
alkane and the number of moles of oxygen gas needed for complete combustion of the
alkane?
M/J-03-01
Q121. The isomers, citric acid and isocitric acid, are intermediates in the Krebs cycle of the
oxidation of glucose in living cells.
KAMRAN SHAHZAD 38
How many chiral centres does each acid possess?
M/J-03-01
Q122. The compound hex-3-en-1-ol, P, has a strong ‘leafy’ smell of newly cut grass and is used in
perfumery.
What is produced when P is treated with an excess of hot concentrated acidic KMnO4?
M/J-03-01
Q123. How many structural and cis-trans isomers are there for dichloropropene, C 3H4Cl2?
A. 3 B. 5. C. 6. D. 7
M/J-03-01
Q124. Which compound is both chiral and acidic?
KAMRAN SHAHZAD 39
O/N-02-01
Q125. Camphor is used for medical purposes; the diagram shows its structure.
How many chiral centres are present in one molecule of camphor?
A. 0 B. 1 C. 2 D. 3
O/N-02-01
Q126. Chloroethane is used as a starting material for the production of ‘time-realease capsules’ in
pharmaceutical products. One way of preparing chloroethane is to react chlorine and ethane
in the presence of untraviolet light.
Which statement is correct about the first stage of the mechanism of this reaction?
A. The Cl – Cl bond is split homolytically.

B. The Cl – Cl bond is split heterolytically.
C. The C – H bond is split homlytically.
D. The C – H bond is split heterolytically.
O/N-02-01
Q127. The anaesthetic halothane, CF3CHBrCl, is made industrially as shown below.
HF Br2
CCl2 = CHCl CF3CH2Cl CF3CHBrCl
Stage 1 Stage 2
KAMRAN SHAHZAD 40
What type of reaction is occurring in stage 2?
C. Free radical substitution
D. Nucleophilic addition
M/J-02-01
Q128. What is the total number of different chloroethanes (formula C2H6-nCln, where n can be any
integer from 1 to 6)?
A. 6 B. 8 C. 9 D. 10
M/J-02-01
Q129. Polymerisation of chloroethene gives pvc.
How does the carbon-carbon bond in pvc compare with that in chloroethene?
A. Longer stronger
B. Longer weaker
C. Shorter stronger
D. Shorter weaker
M/J-02-01
Q130. In 1865 Kekule suggested a ring structure for benzene, C6H6, in which a hydrogen atom is
attached to each carbon atom.
In this structure all of the bonds remain in the places shown. Assuming this is the structure
of benzene, how many isomers of dichlorobenzene, C6H4Cl2, would exist?
A. 3 B. 4 C. 5 D. 6
O/N-16-11
Q131. The diagram shows the structure of vitamin A.
KAMRAN SHAHZAD 41
How many chiral centers are present in one vitamin A molecule?

A. 0 B. 1 C. 2 D. 3
O/N-16-11
Q132. PVC is difficult to dispose of. Two possible methods are burying it in landfill sites and disposal
by combustion.
Which row of the table is correct?
O/N-16-11
Q133. Limonene is found in lemon and orange oils.
What will be the major product when limonene is reacted with an excess of dry hydrogen
chloride?
KAMRAN SHAHZAD 42
O/N-16-12
Q134. The compound rotundone is responsible for the peppery smell of pepper and I also found in
some red wines.
How many hydrogen atoms are in one molecule of rotund one?

A. 15 B. 19 C. 22 D. 24
O/N-16-12
Q135. Which statement about stereoisomers is correct?
A. Cis-trans isomers are mirror images of each other.
B. Optical isomers must contain a double bond that restrict rotation.
C. Stereoisomers have the same structural formula as each other.
D. Stereoisomers must contain a chiral centre.
O/N-16-12
Q136. The diagrams show two different compounds.
What is
 The total number of structural isomers, including compound 2, that could be

formed by adding a second methyl group to the ring of compound 1,
 The number of π electrons in each compound?
KAMRAN SHAHZAD 43
M/J-16-11
Q137. The first propagation step in the reaction between methane and chlorine is shown.
How many different first propagation steps are possible in the reaction between pentane
and chlorine?
A. 2 B. 3 C. 4 D. 5
M/J-11-16
Q138. Which stage in the free radical substitution of ethane by chlorine has the lowest activation
energy?
M/J-16-12
Q139. Chlorofluorocarbons damage the ozone layer by undergoing reactions with a free radical
mechanism. The first stage of this is initiation.
Which equation is most likely to be the initiation stage when chlorofluoromethane is
involved in such a reaction?
KAMRAN SHAHZAD 44
M/J-16-12
Q140. Oct- 1 –ene, CH3(CH2)5CH=CH2, can be thermally cracked.
Which combination of compounds W, X, Y and Z can be obtained by thermally cracking oct- 1

–ene?
M/J-16-12
Q141. A cycloalkane with the molecular formula C7H12 was oxidised by hot concentrated acidified
MnO4-. The only organic product was 2-methylexane-1, 6-dioic acid.
What is the identity of the cycloalkane?
M/J-16-12
Q142. The diagram shows the structure of 1, 3-butadiene.
The addition reaction between 1,3-butadiene and two molecules of hydrogen bromide can
produce three structurally isomeric products.
How many of these products have at least one chiral centre?
KAMRAN SHAHZAD 45
A. 0 B. 1 C. 2 D. 3
M/J-16-13
substitution.
In a propagation step a free radical is formed.
How many different structures of are possible?
A. 2 B. 3 C. 4. D. 5
M/J-16-13
Q144. Hexamine is a crystalline solid used as a fuel portable stoves.
The diagram shows its skeletal structure.
What is the empirical formula of hexamine?

A. CH2N B. C3 H 6 N 2 C. C4 H 8 N 4 D. C6H12N4
O/N-15-11
Q145. How many isomeric esters have the molecular formula C4H8O2?
A. 2 B. 3 C. 4 D. 5
O/N-15-11
Q146. A new jet fuel has been produced that is a mixture of different structural isomers of
compound Q.
Which skeletal formula represents a structural isomer of Q?
KAMRAN SHAHZAD 46
O/N-15-11
Q147. Crude oil is a mixture of many hydrocarbons ranging in size from 1 to 40 carbon atoms per
molecule. The alkanes in crude oil can be separated because they have different boiling
points.
The table below shows the boiling points of some alkanes.
What is the correct explanation for the difference in the boiling points of the three isomers
with Mr = 72?
A. Boiling point is dependent upon the length of the carbon chain only.
B. Increased branching on a carbon chain increases the boiling point.
C. Increased branching reduces the strength of the intermolecular hydrogen bonding.
D. Increased branching reduces the strength of the intermolecular van der Waals’ forces.
O/N-15-11
Q148. Sorbitol is a naturally-occurring compound with a sweet taste. It is often used as a substitute
for sucrose by the food industry.
KAMRAN SHAHZAD 47
How many chiral centres are present in sorbitol?
A. 3 B. 4 C. 5 D. 6
O/N-15-11
Q149. Which compound shows optical isomerism?
A. 2-chloropropane
B. 1,2-dichloropropane
C. 1,3-dichloropropane
D. 2,2-dichloropropane
O/N-15-12
Q150. X has the molecular formula C5H12O. X has a branched carbon skeleton and a secondary
alcohol functional group.
How many structural isomers fit this description of X?
A. 1 B. 2 C. 3 D. 4
O/N-18-11
Q151. A new jet fuel has been produced that is a mixture of different structural isomers of
compound Q.
Which skeletal formula represents a structural isomer of Q?
KAMRAN SHAHZAD 48
O/N-18-11
Q152. An organic molecule W contains 3 carbon atoms. It requires 4.5 molecules of oxygen for
complete combustion.
What could W be?
A. Propane
B. Propanoic acid
C. Propanone
D. Propan-1-ol
O/N-18-11
Q153. There are three structural isomers with the formula C5H12.
Which formulae correctly represent these three structural isomers?
O/N-18-12
Q154. Polyethene is made by the polymerization of ethane.
Which statement is correct?
A. The monomer and the polymer have different empirical formulae.
B. The monomer can be oxidized without heat whereas the polymer cannot.
C. The monomer can be used as a fuel whereas the polymer cannot.
D. The monomer has greater van der Waal’s forces than the polymer.
KAMRAN SHAHZAD 49
O/N-18-12
Q155. Which statement about compound Q is correct?
O/N-18-12
Q156. Which fuel would produce the largest mass of CO2 when 10 kg of the fuel undergo complete
combustion?
A. Biodiesel, C17H34O2
B. Ethanol, C2H6O
C. Octane, C8H18
D. Propane, C3H8
M/J-18-11
KAMRAN SHAHZAD 50
Q157. Fructose is a sugar with more than one chiral centre. The fructose molecule is shown with X,
Y and Z indicating three carbon atoms.
Which carbon atoms are chiral centres?

A. X, Y and Z B. X and Y only C. X only D. Y only
M/J-18-11
Q158. Compound Y is treated with an excess of hydrogen gas in the presence of a nickel catalyst.
The produce is fully saturated.
What is the number of chiral carbon atoms in the product?

A. 5 B. 6 C. 7 D. 8
M/J-18-12
Q159. Which equation represents a valid propagation step in chlorination of ethane?
M/J-18-12
Q160. Maleic acid is used in the food industry and for stabilizing drugs. It is the cis-isomer of
butenedioic acid and has the structural formula HO2CCH=CHCO2H.
What is the product formed from the reaction of maleic acid with cold, dilute, acidified
manganate(VII) ions?
KAMRAN SHAHZAD 51
A. HO2CCH(OH)CH(OH)CO2H
B. HO2CCO2H
C. HO2CCH2CH(OH)CO2H
D. HO2CCOCOCO2H
M/J-18-12
Q161. Which statement is not correct?
A. Combustion of PVC produces a highly acidic gas.
B. PVC molecules are saturated.
C. The empirical formula of PVC is the same as the empirical formula of its monomer.
D. The repeat unit of PVC is
M/J-18-13
Q162. Molecule G is shown.
How many chiral centres are present in each molecule of G?

A. 1 B. 2. C. 3 D. 4
M/J-18-13
Q163. Sibirene, C15H24, is reacted with an excess of HBr(g). The major product is X.
What is the skeletal formula of X?
KAMRAN SHAHZAD 52
M/J-18-13
Q164. What is the name of compound X?
A. Trans-2-hydroxyhex-3-ene
B. Trans-2-hydroxyhexene
C. Trans-5-hydroxyhex-3-ene
D. Trans-5-hydroxyhexene
O/N-17-11
Q165. The structural formula of compound Q is sown.
How many stereoisomers exist with this structural formula?

A. 1 B. 2 C. 4 D. 8
O/N-17-11
Q166. A section of an addition polymer chain is shown.
Which monomer could be used to make this polymer?

A. CH2CHCH2Cl
B. CH2CHCl
C. CH3CHCHCl
D. CHClCHCH2CH2Cl
O/N-17-11
KAMRAN SHAHZAD 53
Q167. Ethene is reacted with steam in the presence of concentrated H 3PO4. The product of this
reaction is added to acidified potassium dichromate(VI) and heated under reflux for one
hour. The final organic product is collected and labelled X.
But-2-ene is treated with hot, concentrated, acidified potassium manganate(VII). The final
organic product is collected and labelled Y.
A. One molecule of X has more carbon atoms than one molecule of Y.
B. One molecule of Y has more carbon atoms than one molecule of X.
C. X and Y have different functional groups.
D. X is the same compound as Y.
O/N-17-11
Q168. Two hydrocarbons have the formula CwHx and CyHz. W, X, Y and Z represent different whole
numbers.
Which row is correct when comparing the two hydrocarbons?
O/N-17-12
Q169. Which compound does not exhibit stereoisomerism?
A. CH3CHClCH2CHO
B. CH3CHCHCH3
C. CH2ClCH2CCl2H
D. CHClCHCl
O/N-17-12
Q170. The diagram shows the skeletal formula of citric acid.
KAMRAN SHAHZAD 54
What is the molecular formula of citric acid?
A. C6 H 8 O 7 B. C6 H 4 O 7 C. C8 H 8 O 7 D. C10H8O7
O/N-17-12
Q171. Which types of bond are broken and formed in the addition polymerization of alkenes?
O/N-17-12
Q172. Which compound would produce two different carboxylic acids when treated with hot,
concentrated, acidified manganate(VII) ions?
O/N-17-12
Q173. 2,3-dimethylpent-2-ene, (CH3)2C=C(CH3)CH2CH3, is treated with cold, dilute KMnO 4. The
product of this reaction is treated with an excess of concentrated H 2SO4 at 180oC, giving a
mixture of isomeric hydrocarbons with molecular formula C7H12.
What is the name of one of the isomeric hydrocarbons?
A. 2,3-dimethylpenta-1,2-diene
B. Cis-2,3-dimethylpenta-1,3-diene
C. 2,3-dimethylpenta-1,4-diene
D. 3,4-dimethylpenta-1,3-diene
O/N-17-12
Q174. The drug cortisone has the formula shown.
KAMRAN SHAHZAD 55
In addition to those chiral centres marked by an asterisk (*), how many other chiral cenres
are present in the cortisone molecule?
A. 0 B. 1 C. 2 D. 3
M/J-17-11
Q175. An alkaline is reacted with acidified manganate(VII) ions, MnO4-. The desired organic product
has a relative molecular mass greater than that of the alkene by 34.
What conditions should be used?
A. Cold, concentrated MnO4-
B. Cold, dilute MnO4-
C. Hot, concentrated MnO4-
D. Hot, dilute MnO4-
M/J-17-11
Q176. The diagram shows a short length of an addition polymer chain.
The polymer has a relative molecular mass of approximately 10 000.

Approximately how many monomer units are joined together in each polymer molecule?
A. 180 B. 360 C. 625 D. 710
M/J-17-11
Q177. Geraniol and linalool are compounds found in some flower fragrances.

A. They are chain isomers of each other.
B. They are geometrical isomers of each other.
C. They are optical isomers of each other.
KAMRAN SHAHZAD 56
D. They are positional isomers of each other.
M/J-17-12
Q178. Which equation represents the initiation step of the substitution reaction between methane
and chlorine?
M/J-17-12
Q179. Structural isomerism and stereoisomerism should be considered when answering this
question. If a molecule contains two non-identical chiral carbon atoms, four optical isomers
exist.
How many isomers are there with
 molecular formula C7H14O and
 a five-membered ring and
 a tertiary alcohol group?
A. 4 B. 5 C. 9 D. 13
M/J-17-13
Q180. Which equation correctly describes the complete combustion of an alkene, C nH2n?
M/J-17-13
Q181. Structural isomerism and stereoisomerism should be considered when answering this
question.
Which formula identifies a single substance?
A. CH3CHClCH2CHO
B. CH3CHCHCH3
C. CH2ClCH2CHCl2
D. C4H10
M/J-17-13
Q182. The diagram represents the structure of a polymer.
KAMRAN SHAHZAD 57
By which method might this polymer be made?

A. Polymerise ethene followed by hydration
B. Polymerise ethene followed by oxidation with cold, acidified KMnO4
C. Polymerise 1,2-dichloroethene followed by hydrolysis
D. Polymerise 1,2-dichloroethene followed by oxidation with cold, acidified KMnO 4
M/J-17-13
Q183. Bromine reacts with ethene in the dark.
Which description of the organic intermediate in this reaction is correct?
A. It has a negative charge.
B. It is a free radical.
C. It is a nucleophile.
D. It is an electrophile.
M/J-17-13
KAMRAN SHAHZAD 58
SECTION - B
For each of the question in this section, one or more of the three numbered statements 1 to 3 may
be correct.
Decide whether each of the statements is or is not correct (you may find it helpful to put a tick
against the statements that you consider to be correct).
The responses A to D should be selected on the basis of
A B C D
1, 2 and 3 1 and 2 2 and 3 1 only
are only are only are is
correct correct correct correct
No other combination of statements is used as a correct response.
Q184. The diagram shows the structure of an alkene molecule.
Which statement about this molecule are correct?
1. All the carbon atoms are in the same plane.

2. It has geometrical isomers.
3. It is optically active
M/J-15-11
KAMRAN SHAHZAD 59
Q185. Which compounds will react with HBr to give the compound R?
M/J-15-11
Q186. Halogenated hydrocarbons have many uses.

What have halogenated hydrocarbons been used for?
1. Solvents
2. Refrigerants
3. Monomers in polymer manufacture
M/J-15-12
Q187. Which statements about the photochemical chlorination of ethane are correct?
1. A propagation step in the mechanism is
2. Butane is present in the products.
3. The initiation step is the heterolytic fission of chlorine.
O/N-14-13
Q188. Which compounds produce pent-2ene as either one of the products, or as the only product,
on heating with potassium hydroxide in ethanol?
1. CH3CH2CH2CH2CH2Br
2. CH3CHBrCH2CH2CH3
3. CH3CH2CHBrCH2CH3
O/N-14-13
Q189. Which molecules would be present in the mixture produced by the photochemical
chlorination of methane?
1. Hydrogen
2. Hydrogen chloride
3. Dichloromethane
KAMRAN SHAHZAD 60
M/J-13-11
Q190. Which substances contain delocalized electrons?
1. Cyclohexene
2. Graphite
3. Sodium
M/J-13-12
Q191. Which compounds can be obtained from propene in a single reaction?
M/J-12-12
Q192. What are the same for a pair of optical isomers?
1. Their empirical formula

2. Their functional groups
3. Their structural formula
M/J-12-12
Q193. Which statements about the photochemical chlorination of ethane are correct?
1. Hydrogen gas is one of the products.
2. A propagation step in the mechanism is
3. The initiation step is the hemolytic fission of chlorine.
M/J-12-12
Q194. The definitions of many chemical terms can be illustrated by chemical equations.
Which terms can be illustrated by an equation that shows the formation of a positive ion?
1. First ionization energy
2. Heterolytic fission
3. Enthalpy change of atomisation
O/N-11-13
Q195. The diagram shows the structure of the naturally-occurring molecule cholesterol.
KAMRAN SHAHZAD 61
Which statements about cholesterol are correct?
1. The molecule contains a secondary alcohol group.

2. The molecule contains two π bonds.
3. All carbon atoms in the four rings lie in the same plane.
O/N-10-11
Q196. Which compounds can be obtained from ethane in a single reaction?
M/J-11-12
Q197. Which structural formulae represent 2,2-dimethylpentane?
M/J-10-12
Q198. A compound has a relative molecular mass of 88 and its molecule contains only four carbon
atoms.
What could this compound be?
1. A saturated non-cyclic diol

2. A secondary alcohol containing an aldehyde group
3. A primary alcohol containing a ketone group
O/N-09-12
Q199. A fraction of distilled crude oil contains molecules with between 15 and 19 carbon atoms.
This fraction is cracked by strong heating.
Why is this done?
1. To produce alkenes.
2. To produce smaller molecules which are in higher demand.
KAMRAN SHAHZAD 62
3. To insert oxygen atoms into the hydrocarbons.
M/J-09-01
Q200. Kevlar has the structure below.
Compared to a steel rope of similar dimensions, a Kevlar rope is both lighter and stronger.
Which properties of Kevlar help to explain these facts?
1. The fibers of Kevlar align due to hydrogen bonding.

2. The mass per unit length is less in a Kevlar rope than in a steel rope.
3. The Kevlar molecule has no permanent dipole.
O/N-08-01
Q201. Which statements about alkenes are correct?
1. They are formed when higher alkanes are cracked.

2. They are used as monomers for polymerisation.
3. They are less reactive than alkanes towards electrophiles.
O/N-08-01
Q202. During the bromination of methane, the free radical is generated and a possible
terminating step of this reaction is the formation of C 2H6 by the combination of two free
radicals.
O/N-08-01
Q203. The following three hydrocarbons all occur naturally.
Which of these will be split into two organic compounds, both containing a ketone group,
when treated with hot acidified potassium manganite (VII)?
KAMRAN SHAHZAD 63
O/N-06-01
Q204. In which pairs are the members stereoisomers of each other?
M/J-06-01
Q205. The sex-attractant of the house-fly is muscalure, with the following formula.
Which statements about muscalure are correct?
1. It will decolourise aqueous bromine.

2. It will be oxidised by cold aqueous alkaline KMnO4 to give a diol.
3. It will be optically active.
O/N-05-01
Q206. Which compounds may result from mixing ethane and chlorine in the presence of sunlight?
KAMRAN SHAHZAD 64
1. CH3CH2Cl
2. CH3CH2CH2CH3
3. CH3CHClCHClCH3
O/N-04-01
Q207. Which molecules would be present in the photochemical chlorination of methane?
1. Hydrogen
2. Hydrogen chloride
3. Dichloromethane
O/N-03-01
Q208. The taste buds on the tongue are chiral and can distinguish one optical isomer from another.
Which naturally-occurring compounds will have optical isomers that may be distinguished by
taste?
O/N-03-01
Q209. What will always be a characteristic of a compound containing a single carbon atom with
four different groups bonded to it?
1. It will have an optical isomer.

2. It will have a chiral centre.
3. It will have a structural isomer.
M/J-03-01
Q210. Which compounds have the empirical formula CH2O?
1. Methanol
KAMRAN SHAHZAD 65
2. Ethanoic acid
3. Methyl methanoate
O/N-02-01
Q211. Which compounds show cis-trans isomerism?
1. But-2-ene
2. But-1-ene
3. 2-methylpropene
O/N-02-01
Q212. When octane is subjected to catalytic cracking, which compounds can be obtained?
1. CH2 = CH2
2. CH3CH2CH = CH2
3. CH3(CH2)4CH3
O/N-02-01
Q213. Which pairs of compounds have the same empirical formula?
1. Ethane and ethene

2. Ethene and cyclohexane
3. Cyclohexane and oct-1-ene
M/J-02-01
Q214. Which compounds would be formed in the reaction of ethene with aqueous bromine in the
presence of sodium chloride?
1. CH2ClCH2Cl
2. CH2BrCH2Cl
3. CH2BrCH2Br
M/J-02-01
Q215. A cathedral in New Zealand has been constructed from cardboard. Cardboard contains
polymer molecules. Part of one such polymer molecule is shown below.
KAMRAN SHAHZAD 66
Which statements about this polymer are correct?
1. The polymer molecules can form hydrogen bonds with each other.
2. The polymer can form intermolecular forces with water molecules.
3. The polymer will not burn easily because it is a secondary alcohol.
O/N-16-12
Q216. A species of termite produces a chemical defence secretion which contains the molecule
shown.
To help determine the structure of this compound, it is treated with hot, concentrated,
acidified manganate (VII) ions.
Which compound are produced in this reaction?
1. CO2
2. CH3COCH3
3. CH3CO2H
O/N-16-12
Q217. The diagram shows the structure of cyclohexene.
Which structures could be formed by addition reaction with cyclohexene as the only
reactant?
KAMRAN SHAHZAD 67
M/J-16-11
Q218. One of the active ingredients in tea-tree oil is terpinen-4-ol.
In the diagram of the skeletal formula of terpinen-4-ol, three of the carbon atoms are
labelled 1, 2 and 3.
Which of the labelled carbon atoms are chiral?
M/J-16-12
Q219. Compound Z is heated with concentrated acidified potassium manganate(VIII). This produces
an equimolar mixture of CO2 and CH3COCH2CH2CH(COCH3)CH2CO2H.
What could be the structural formula of Z?
O/N-15-12
Q220. 2-methylpropene can react in more than one way with chlorine.
One of the reactions follows the pathway shown.
KAMRAN SHAHZAD 68
Witch statements about this mechanism are correct?
1. The intermediate has all carbon atoms in the same plane.
2. There is an electrophilic attack on the double bond.
3. It is a free radical mechanism.
O/N-18-11
Q221. Which bromopropenes would react with cold bromine in the dark to form a product
containing a chiral carbon atom?
1. CHBr=CHCH3
2. CH2=CHCH2Br
3. CH2=CBrCH3
O/N-18-12
Q222. Polymer Z contains the length of polymer chain shown below.
This short length of chain is found many times within the chains of polymer Z, although it is
not the repeat unit.
What would be the name of polymer Z?

1. Poly(2-chloropropene)
2. Poly (chloroethene)
3. PVC
M/J-18-11
Q223. Limonene is found in lemons.
KAMRAN SHAHZAD 69
Limonene is heated with concentrated acidified potassium manganate(VII).

Which compounds are produced?
1. CH3COCH2CH2CH(CH2CO2H)2
2. CO2
3. CH3COCH2CH2CH(COCH3)CH2CO2H
M/J-18-11
Q224. Which compounds show geometrical (cis-trans) isomerism?

1. CH3CH=C(CH3)C2H5
2. CH3CH=CHCH2CH2CH3
3. C2H5CH=CHC2H5
M/J-18-12
Q225. In which molecules do all the carbon atoms lie in the same plane?
1. 2,3-dimethylbut-2-ene
2. Propane
3. Cyclohexane
O/N-17-11
Q226. P and Q are a pair of cis-trans isomers.
What must be the same for P and Q?
1. Their empirical formula
2. Their functional groups
3. Their skeletal formula
M/J-17-11
Q227. Which compounds contain a chiral centre?
1. 2-huydroxybutanoic acid
2. 3-hydroxybutanoic acid
3. 4-hydroxybutanoic acid
M/J-17-12
Q228. The diagram shows the monomer used to make polyvinyl chloride, PVC.
KAMRAN SHAHZAD 70
Assuming that one particular molecule of the polymer forms from n molecules of the
monomer (where n is many thousands), which statements are correct?
1. The relative molecular mass of this polymer molecule is approximately 62.5n.
2. There are n chiral carbon atoms in this polymer molecule.
3. There are 5n σ bonds in one polymer molecule.
M/J-17-12
SECTION - C
Q1. In each section of this question an organic compound is shown. For each compound give it
name and answer the questions about it.
(a). CH3CH2CH(CH3)CH=CHCH3
(i). name ……………………………………………………………………………………………………………….

[1]
(ii). This compound shows stereoisomerism.
Define stereoisomerism.
………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
[1]
(iii). State and explain how many stereoisomers of this structure there are.
………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
[4]
(b). (CH3)2C=C(CH3)2
(i). name ……………………………………………………………………………………………………………….
KAMRAN SHAHZAD 71
[1]
(ii). Draw the skeletal formula of the organic product of the reaction of this
compound with cold, dilute, acidified manganite(VII) ions.
[1]
(iii). Name the organic product of the reaction of this compound with hot,
concentrated, acidified manganite(VII) ions.
…………………………………………………………………………………………………………………………
[1]
(iv). Draw the structure of part of a molecule of the addition polymer formed from
this compound, showing exactly three repeat units.
[1]
(c). (CH3)2C=CH2
(i). name ……………………………………………………………………………………………………………….

[1]
(ii). Complete the mechanism for the reaction of this compound with hydrogen
bromide. Include all necessary curly arrows, lone pairs, charges and partial
charges.
[4]
(iii). Explain fully with 2-bromomethylpropane is the major product of this reaction
while only relatively small amounts of 1-broomethylpropne are produced.
KAMRAN SHAHZAD 72
………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
[4]
O/N-16-21
Q2. This question is about molecules with molecular formula C4H8.
(a). Give the structures of a pair of positional isomers with the formula C4H8.
[1]
(b). Give the structures of a pair of chain isomers with the formula C4H8, that do not
exhibit stereoisomerism.
[1]
(c). Give the structures and full names of a pair of stereoisomers with the formula C4H8.
KAMRAN SHAHZAD 73
[2]
(d). The structure of a molecule, A, of formula C4H8 is shown.
Draw a functional group isomer of molecule A in box B. Explain how molecules A and
B could be distinguished by a chemical test.
…………………………………………………………………………………………………………………………………….
…………………………………………………………………………………………………………………………………….
…………………………………………………………………………………………………………………………………….
[3]
M/J-16-21
Q3. Crude oil is a mixture of hydrocarbons and provides many useful chemicals when processed.
Two of the stages involved in the processing of crude oil are fractional distillation and
cracking.
(a). The diagram is a simplified representation of a fractional distillation column.
KAMRAN SHAHZAD 74
(i). What is to be done to the crude oil before it enters the column?
…………………………………………………………………………………………………………………………
[1]
(ii). What trend in structure is there from fraction A to fraction F?
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
[1]
(iii). State the trends in two properties of the fractions from A to F.
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
[2]
(b). The naphtha fraction from fractional distillation of crude oil is used as a starting
material for cracking.
(i). Write an equation for the cracking of C12H26 to form the products ethane and
one other hydrocarbon in a 2 : 1 mole ratio.
…………………………………………………………………………………………………………………………
[1]
KAMRAN SHAHZAD 75
(ii). Suggest a use for each of the products from your equation in (i). Explain what
makes each products from (i) suitable for the use you suggest.
Use of ethane ………………………………………………………………………………………………….
…………………………………………………………………………………………………………………………
Explanation ……………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
Use of other product ………………………………………………………………………………………
…………………………………………………………………………………………………………………………
Explanation ……………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………
[4]
M/J-16-23
Q4. Heptane, C7H16, is an undesirable component of petrol as it burns explosively causing

‘knocking’ in an engine.
(a). There are nine structural isomers with the formula C7H16, only two of which contain
chiral centres.
(i). Explain the meaningsofthe terms structural isomers and chiral.
Structural isomers ………………………………………………………………………………………….
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
chiral………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
[2]
KAMRAN SHAHZAD 76
(ii). Give the structures and names of the two structural isomers of C7H16 which
contain a chiral centre.
[4]
(b). (i). Write an equation for the complete combustion of heptane.
………………………………………………………………………………………………………………………..
[1]
(ii). Write an equation for the incomplete combustion of heptane leading to the
production of a solid pollutant.
………………………………………………………………………………………………………………………..
[1]
(iii). Incomplete combustion can also lead to emission of unburnt hydrocarbons.
State one environmental consequence of this.
………………………………………………………………………………………………………………………..
[1]
(c). The reaction of heptane with chlorine in the presence of UV light produces a wide
variety of products.
Formation of the monochloroheptanes can be represented by the following equation
(i) Name the mechanism of the reaction between heptane and chlorine in the
presence of UV light.
………………………………………………………………………………………………………………………..
[1]
(ii). Describe this mechanism, using suitable equations and including the names of
each stage in the process.
KAMRAN SHAHZAD 77
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
[5]
O/N-15-21
Q5. Ethane reacts with chlorine to form chloroethane.
(i). Use bond energies from the Data Booklet to calculate the enthalpy change for
this reaction.
enthalpy change = ………………………………… kJ mol-1

[3]
(ii). State the conditions needed for this reaction to occur.
…………………………………………………………………………………………………………………………………..
[1]
(iii). Use a series of equations to describe the mechanism of this reaction including the
names of each stage and an indication of how butane can be producedas a minor by-
product.
……………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………
KAMRAN SHAHZAD 78
……………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………
[5]
M/J-15-22
Q6. P, Q and R are structural isomers with the molecular formula C4H8.
All three compounds readily decolourise bromine in the dark
P and Q do not exhibit stereoisomerism but R exists as a pair of geometrical (cis-trans)

isomers.
All three compounds react with hotconcentrated, acidified potassium manganite(VII) to

produce a variety of products as shown in the table.
S reacts with 2, 4-dinitrophenylhydrazine reagent, 2,4-DNPH, to form an orange crystalline

product but does not react with Fehling’s reagent.
(a). Give the structural formulae of P, Q, R and S.
P ……………………………………………………… Q ………………………………………………………
R ……………………………………………………… S ………………………………………………………
[4]
(b) (i). Explain what is meant by the term stereoisomerism.
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
[2]
(ii). Draw the displayed formulae of the geometrical isomers of R and name them
both.
KAMRAN SHAHZAD 79
name …………………………………………… name ………………………………………….......

[2]
(c). State a reagent that could be used for the reduction of S and name the organic
product of this reduction.
reagent …………………………………………… product ………………………………………….......

[2]
O/N-14-21
Q7. The molecular formula C3H6 represents the compounds propene and cyclopropane.
(a). What is the H-C-H bond angle at the terminal = CH2 group is propene?
……………………… [1]
(b). Under suitable conditions, propene and cyclopropane each react with chlorine.
(i). With propene, 1,2-dichloropropane, CH3CHClCH2Cl is formed.
State fully what type of reaction this is
………………………………………………………………………………………………………………………
[1]
(ii). When cyclopropane reacts with chlorine, three different compounds with the
molecular formula C3H4Cl2 can be formed.
Draw displayed structures of each of these three compounds.
KAMRAN SHAHZAD 80
[3]
O/N-13-22
Q8. Octadecane, C18H38, is a long chain hydrocarbon which is present in crude oil. Such long chain
hydrocarbons are ‘cracked’ to produce alkanes and alkenes which have smaller molecules.
(a). Give two different conditions under which long chain molecules may be cracked.
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
[2]
(b). Octadecane, C18H38, can be cracked to form hexane and an alkene.
Write a balanced equation for this reaction.
…………………………………………………………………………………………………………………………….. [1]
Alkenes are important industrially because the C = C bond makes them very reactive.
(c). Ethene reacts with bromine to give 1, 2-dibromoethane.
(i). What type of reaction is this ?
…………………………………………………………………………………………………………………………
(ii). Outline the mechanism of this reaction, giving the structure of the
intermediate.
Show clearly any relevant dipoles, charges and lone pairs of electrons.
KAMRAN SHAHZAD 81
[4]
O/N-06-02
Q9. The molecular formula of a compound states the number of atoms of each element that are
present in one molecule. It contains no information about the structure of the molecule.
Hydrocarbons with the molecular formula C5H10 may be branched chain, straight chain or
cyclic.
(a). Draw a displayed formula of C5H10 as a branched chain hydrocarbon.
Pent-2-ene is one straight chain hydrocarbon with formula C5H10. [1]
(b). Pent-2-ene exhibits cis-trans isomerism. Draw and label the structural formulae of
the two cis-trans isomers of pent-2-ene.
[2]
O/N-07-02
Q10. Two types of isomerism found in organic compounds are structural isomerism and cis-trans
isomerism.
(a). Draw displayed formulae for
KAMRAN SHAHZAD 82
(i). Two structural isomers of C2H4Br2,
(ii). The cis- and the trans- isomers of C2H2Br2.
[4]
(b). (i). The cis- isomer of C2H2Br2 can be converted into one of the structural
isomers of C2H4Br2. State the reagent (s) and conditions you would use to do
this.
……………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………
(ii). Which of your structural isomers, D or E, would be formed? Explain your

answer.
Isomer formed is ………………………..
Reason …………………………………………………………………………………………………………….
[3]
M/J-08-02
Q11. (a). (i). By using equations, describe the mechanism of the reaction between chlorine
KAMRAN SHAHZAD 83
and methane to form chloromethane, CH3Cl.
Identify, by name, the separate steps of the overall reaction.
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
(ii). What is the intermediate organic species in this reaction?
………………………………………………………………… [7]
(b). The energy of activation for the formation of CH3Cl is 16 kJ mol-1.

Use this figure and your answer to (a)(i) to complete the reaction pathway diagram
below showing the formation of CH3Cl from CH4 and Cl2.
Show clearly the intermediate organic species and the final products.
Indicate on your sketch the relevant enthalpy change and their values
[4]
O/N-09-21
Q12. Give the structural formula of the organic product formed when propene reacts separately
with each of the following substances.
(i). bromine
KAMRAN SHAHZAD 84
(ii). Cold, dilute manganite (VII) ions.
(iii). Hot, concentrated manganite (VII) ions.
[3]
M/J-10-22
Q13. Astronomers using modern spectroscopic techniques of various types have found evidence
of many molecules, ions and free radicals in the dust clouds in Space. Many of the
species concerned have also been produced in laboratories on Earth.
Two such species are the dicarbon monoxide molecule, C2O and the amino free radical, NH2.
(a). (i). Dicarbon monoxide can be produced in a laboratory and analysis of it shows
that the sequence of atoms in this molecule is carbon-carbon-oxygen and
there are no unpaired electrons, but one of the atoms is only surrounded by
six electrons.
Draw a ‘dot-and-cross’ diagram of C2O and suggest the shape of the molecule.
Shape …………………………………………
(ii). What is meant by the term free radical?
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
KAMRAN SHAHZAD 85
(iii). Explain why NH2 is described as a ‘free radical”.
………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………. [5]
O/N-10-23
Q14. Crude oil is a naturally occurring flammable liquid which consists of a complex mixture of
hydrocarbons. In order to separate the hydrocarbons, the crude oil is subjected to fractional
distillation.
(a). Explain what is meant by the following terms.
(i). hydrocarbon ………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
(ii). Fractional distillation ……………………………………………………………………………………..
……………………………………………………………………………………………………………………….
[2]
(b). Undecane, C11H24, is a long chain hydrocarbon which is present in crude oil.
Such long chain hydrocarbons are ‘cracked’ to produce alkanes and alkenes which
have smaller molecules.
(i). Give the conditions for two different processes by which long chain
molecules may be cracked.
Process 1 …………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
Process 2 …………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………
(ii). Undecane, C11H24, can be cracked to form pentane, C5H12, and an alkene.
Construct a balanced equation for this reaction.
…………………………………………………………………………………………………………………………
[3]
Pentane, C5H12, exhibits structural isomerism.
(c). (i). Draw the three structural isomers of pentane.
KAMRAN SHAHZAD 86
[3]
O/N-10-21
Q15. In looking, unsaturated fats are often oxidised to give aldehydes or ketones.
(a). (i). Give the structural formulae of the two aldehydes formed by the partial
oxidation of the unsaturated fat below.
In the structure, X, represents the rest of the fat molecule.
(ii). Name the reagent you would use to show that the product contained either
an aldehyde or a ketone. What change would be seen?
[4]
Animal fats and vegetable oils can become rancid because of oxidation. The rancid fat or oil
has an unpleasant smell and taste.
Antioxidants are used to prevent the spoilage of many foodstuffs by oxidation.

One antioxidant that is widely used in vitamin C, ascorbic acid.
(b). (i). How many chiral carbon atoms are present in one molecule of ascorbic
acid? If none, write ‘none’.
KAMRAN SHAHZAD 87
…………………
(ii). The ascorbic acid molecule contains three functional groups.

Two of these are alcohol (primary and secondary) and alkene.
What is the name of the third functional group?
…………………………………………………………………………… [2]
M/J-11-22
Q16. The gas ethyne, C2H2, more commonly known as acetylene, is manufactured for use in the
synthesis of organic compounds. It is also used, in combination with oxygen, in ‘oxy-
acetylene’ torches for the cutting and welding of metals.
Industrially, ethyne is made from calcium carbide, CaC2, or by cracking liquid hydrocarbons.
(a). When calcium carbide is reacted with water, ethyne and calcium hydroxide are
formed.
Construct a balanced equation for this reaction.
………………………………………………………………………………………………………………………………. [1]
Ethyne can also be obtained from ethene by using the following sequence of
reactions.
(b). (i). What types of reaction are step 1 and step 2?
Step 1 …………………………………………………………………………….
Step 2 …………………………………………………………………………….
(ii). Suggest what reagent and conditions would be used in a laboratory in step 2.
Reagent …………………………………………………………………………….
Conditions ………………………………………………………………………… [5]
KAMRAN SHAHZAD 88
When ethyne is passed into water at 60 oC, in the presence of a little H2SO4 and Hg2+ ions, a
pungent, colourless organic liquid, Q, with Mr of 44 is obtained. This is step 3.
When Q is warmed with Tollens’ reagent in a test-tube, a silver mirror is formed.
On acidification, the solution remaining in the test-tube is found to contain the organic
compound R which has Mr of 60. This is step 4.
(c). (i). Give the structural formulae of Q and R.
(ii). What type of reaction is step 3 and step 4?
Step 3 …………………………………………………………………………………
Step 4 ………………………………………………………………………………… [4]
M/J-11-21
Q17. Crude oil contains a mixture of hydrocarbons together with other organic compounds which
may contain nitrogen, oxygen or sulfur in their molecules.
At an oil refinery, after the fractional distillation of crude oil, a number of other processes
may be used including ‘cracking’, ‘isomerisation’, and ‘reforming’.
(i). What is meant by the term ‘cracking’ and why is it carried out?
……………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………………………….
(ii). Outline briefly how the cracking of hydrocarbons would be carried out.
KAMRAN SHAHZAD 89
…………………………………………………………………………………………………………………………………….
…………………………………………………………………………………………………………………………………….
(iii). Construct a balanced equation for the formation of heptane, C7H16, by

cracking tetradecane, C14H30.
……………………………………………………………………………………………………………………………….
[4]
M/J-11-21
Q18. Analysis of another organic compound, B, gave the following composition by mass: C,
64.86%, H, 13.50%, O, 21.64%.
(i). Use these values to calculate the empirical formula of B.
(ii). The empirical and molecular formulae of B are the same.
B is found to be chiral.
Draw displayed formula of the two optical isomers of this compound, indicating with
an asterisk (*) the chiral carbon atom.
(iii). There are three other structural isomers of B which are not chiral but which contain
the same functional groups as B.
KAMRAN SHAHZAD 90
In the boxes below, draw the structural formulae of these isomers.
[7]
O/N-11-23
Q19. But- 1 –ene, CH3CH2CH = CH2, is an important compound in the petrochemical industry.
(a). Some reactions of but- 1 –ene are given below.
In each empty box, draw the structural formula of the organic compound formed.
[4]
KAMRAN SHAHZAD 91
O/N-11-22
Q20. But-2-ene, CH3CH = CHCH3, is an important compound which is obtained from the cracking of
hydrocarbons present in crude oil.
(a). Give two different conditions under which long chain hydrocarbons may be cracked.
……………………………………………………………………………………………………………………………………
……………………………………………………………………………………………………………………………………
[2]
(b). Dodecane, C12H26, is a long chain hydrocarbon which is present in crude oil and which
can be cracked to form but-2-ene and an alkane.
Write a balanced equation for this reaction.
…………………………………………………………………………………………………………………………… [1]
(c). Some reactions of but-2-ene are shown below.
In the boxes below, give the structural formulae of the organic compounds A to D.
[4]
KAMRAN SHAHZAD 92
(d). (i). Draw the skeletal formula of compound D.
(ii). By using the letters A to D as appropriate, identify those compounds which

are chiral. If there are none, write ‘none’.
…………………………………………………………………………… [3]
(e). But-2-ene can be polymerized to give poly (butane).
Draw the structural formula of a portion of the polymer chain in poly (butane)
showing two repeat units.
[1]
(f). Compound C is a liquid which can be reacted with concentrated sulfuric acid to give a
gas, E, which will decolourise aqueous bromine when passed through it.
(i). Suggest the structural formula of E.
(ii). Suggest the structural formula of the product of the reaction between E and
an excess bromine.
(iii). What type of reaction occurs between E and an excess of bromine?
…………………………………………… [3]
M/J-12-23
KAMRAN SHAHZAD 93
Q21. One method of preparing ethene in a school or college laboratory is from ethanol by using
the apparatus shown below.
(a). (i). Write a balanced equation for this reaction.
………………………………………………………………………………………………………………………..
(ii). What type of reaction is this?
………………………………………………………………………………………………………………………..
(iii). Give the chemical name of a reagent other than pumice that could be used to
carry out this reaction. It is not necessary to use the same apparatus.
…………………………………………. [3]
(b). Ethene is bubbled into two separate tetst-tubes, one containing aqueous hydrogen
bromide and the other containing cold, dilute acidified potassium manganite (VII).
In each case, describe any colour changes you would see and give the structural
formula of the organic product.
KAMRAN SHAHZAD 94
[4]
(c). Cyclohexene has the following structural formula.
(i). What is the molecular formula of cyclohexene?
………………………………….
(ii). Draw the structural formula of the compound formed when cyclohexene is
reacted with bromine.
(iii). State as fully as you can what type of reaction this is.
…………………………………………………………………………………………………………………………
(iv). Draw the structural formula of the compound formed when cyclohexene is
reacted with hot concentrated acidified potassium manganite (VII).
[5]
M/J-12-21
Q22. Petrol and diesel fuel are both used in internal combustion engines.
Petrol may be regarded as having the formula C9H20 and diesel fuel as having the formula
C14H30.
(a). (i). Tw which class of compounds do these two hydrocarbons belong?
…………………………………………………………………..
KAMRAN SHAHZAD 95
(ii). Write a balanced equation for the complete combustion of petrol.
…………………………………………………………………………………………………………………………
[2]
(b). When petrol or diesel fuel are used in internal combustion engines, several different
products of the incomplete combustion of the fuel may be formed.
(i). Name two of these products that do not contain hydrogen.
……………………………………….. and …………………………………
(ii). Choose one of these and state a hazard it causes.
Product …………………………………………………………………………………………………………..
Hazard …………………………………………………………………………………………………………….
(iii). Write a balanced equation for the formation of one of the products in (i) from
diesel fuel.
…………………………………………………………………………………………………………………………
[4]
O/N-13-23
Q23. Propane, C3H8, and butane, C4H10, are components of Liquefied Petroleum Gas (LPG) which is
widely used as a fuel for domestic cooking and heating.
(a). (i). To which class of compounds do these two hydrocarbons belong?
……………………………………………………………….
(ii). Write a balanced equation for the complete combustion of butane.
…………………………………………………………………………………………………………………………
[2]
(b). When propane or butane is used in cooking, the saucepan may become covered by
a solid black deposit.
(i). What is the chemical name for this black solid?
KAMRAN SHAHZAD 96
………………………………………………………
(ii). Write a balanced equation for its formation from butane.
…………………………………………………………………………………………………………………………
[2]
(c). The boiling points of methane, ethane, propane and butane are given below.
(i). Suggest an explanation for the increase in boiling points from methane to
butane.
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
(ii). The isomer of butane, 2-methylpropane, (CH3)3CH, has a boiling point of 261
K. Suggest an explanation for the difference between this value and that for
butane in the table above.
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
[4]
O/N-13-22
Q24. The molecular formula C3H6 represents the compounds propene and cyclopropane.
(a). What is the H – C – H bond angle at the terminal = CH2 group in propene?
………………… [1]
KAMRAN SHAHZAD 97
(b). under suitable conditions, propene and cyclopropane each react with chlorine.
(i). With propene, 1,2-dichloropropane, CH3CHClCH2Cl is formed.
State fully what type of reaction this is.
…………………………………………………………………………………………………………………………
[1]
(ii). When cyclopropane reacts with chlorine, three different compounds with the
molecular formula C3H4Cl2 can be formed.
Draw displayed structures of each of these three compounds.
[3]
O/N-13-22
Q25. Another hydrocarbon, W, with the formula C4H8, reacts with hydrogen bromide, HBr, to give
two products X and Y. X and Y are structural isomers of molecular formula C4H9Br.
Reaction of X with aqueous alkali produces an alcohol, Z that has no reaction with acidified
dichromate (VI).
(i). Give the structure and names of the compounds W, X , Y and Z.
W X
KAMRAN SHAHZAD 98
……………………………………………………… ………………………………………………………
Y Z
……………………………………………………… ………………………………………………………
[4]
(ii). When W reacts with hydrogen bromide. More X than Y is produced. Explain
why.
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
[2]
M/J-14-23
Q26. Crude oil is processed to give a wide variety of hydrocarbons.
(a). Give the names of one physical process and one chemical process carried out during
the processing f crude oil.
Physical process ………………………………………………………………………………………………………….
Chemical process ………………………………………………………………………………………………………..

[2]
(b). Alkanes and alkenes can both be obtained from crude oil.
(i). Explain why alkanes are unreactive.
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………… [2]
(ii). State the bond angles in a molecule of
Ethane,…………………………………………………………………………………………………………….
KAMRAN SHAHZAD 99
ethene, ……………………………………………………………………………………………………………
[1]
(iii). State the shape of each molecule in terms of the arrangement of the atoms
bonded to each carbon atom.
Ethane ………………………………………….. ethene ……………………………………………… [1]
(iv). Explain why these molecules have different shapes in terms of the carbon-
carbon bonds present.
…………………………………………………………………………………………………………………………
…………………………………………………………………………………………………………………… [1]
(c). (i). Use a series of equations to describe the mechanism of the reaction of
ethane with chlorine to form chloroethane. Name the steps in this reaction.
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
[5]
(ii). Write an equation to show how butane could be produced as a by-product of

this reaction.
……………………………………………………………………………………………………………………….
[1]
M/J-14-22
Q27. Alkanes and alkenes both react with bromine.
(a). Explain how and why bromine can be used to distinguish between an alkene and an
alkane.
KAMRAN SHAHZAD 100

…………………………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………………… [2]
(b). The reaction of ethane with bromine forms a mixture of products.
(i). State the essential conditions for this reaction to occur.
…………………………………………………………………………………………………………………………
[1]
(ii). Give the full name of the mechanism of this reaction.
…………………………………………………………………………………………………………………………
[2]
(iii). Give the equation for a termination step that could occur, producing a
hydrocarbon.
…………………………………………………………………………………………………………………………
[1]
(iv). Give the equation for one propagation step involved in the formation of
dibromoethane from bromoethane during this reaction.
…………………………………………………………………………………………………………………………
[1]
(c). The reaction of ethene with bromine forms a single product.
(i). Give the full name of the mechanism of this reaction.
…………………………………………………………………………………………………………………………
[2]
(ii). Complete the diagram below to illustrate this mechanism.

Include all relevant charges, partial charges, curly arrows and lone pairs.
KAMRAN SHAHZAD 101

[4]
M/J-14-21
Q28. (a). CHClF2 is also used to produce the monomer tetrafluoroethene, C2F4.
This monomer can be used to produce poly(tetrafluoroethene), PTFE.
(i). State the type of polymerization that occurs during the production of PTFE.
………………………………………………………………………………………………………………………
[1]
(ii). Draw the repeat unit of PTFE.
[1]
(iii). Suggest why PTFE is used as a coating for cooking pans.
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
[1]
(iv). Waste disposal can cause litter problems.
State two other difficulties associated with the disposal of PTFE.
1. ………………………………………………………………………………………………………….
………………………………………………………………………………………………………….
2. ………………………………………………………………………………………………………….
………………………………………………………………………………………………………….
[2]
O/N-18-21
KAMRAN SHAHZAD 102

Q29. Crude oil is a complex mixture of hydrocarbon molecules.
The hydrocarbon molecules in crude oil are separated by fractional distillation. Fractional
distillation is used because the different hydrocarbon molecules in crude oil have different
boiling points.
(a). Explain why the hydrocarbon molecules in crude oil have different boiling points.
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
[2]
(b). Some of the hydrocarbon molecules obtained from crude oil are processed further by
cracking.
Suggest why some hydrocarbon molecules are processed further by cracking.
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
[1]
(c). Cracking one mole of dodecane, C12H26, produces two molecules of ethene and one
mole of another hydrocarbon molecule.
(i). Write the equation for this cracking reaction.
……………………………………………………………………………………………………………………..
[1]
The ethene can be used is the production of poly(ethene).
(ii). Give the full name of the process used to produce poly(ethene) from ethene.
……………………………………………………………………………………………………………………..
[1]
(iii). Give two reasons why poly(ethene) should be reused or recycled rather than
just thrown away.
KAMRAN SHAHZAD 103

……………………………………………………………………………………………………………………..
……………………………………………………………………………………………………………………..
……………………………………………………………………………………………………………………..
[2]
(iv). Part of a polymer chain, produced by the same type of process as
poly(ethene), is shown.
Give the displayed formula of the monomer used to produce this polymer.
[2]
M/J-18-21
Q30. (a). The reaction of methylpropene, (CH3)2CCH2, with hydrogen bromide, HBr, produces a
mixture of two halogenoalkanes.
One of the halogenoalkanes, 2-bromo-2-methylpropane, is formed as the major

product while 1-bromo-2-methylpropane is formed in small quantities.
(i). Complete the mechanism to show the reaction of methylpropene with HBr to
form the major product.
KAMRAN SHAHZAD 104

Include the structure of the intermediate and all necessary charges, dipoles,
lone pairs and curly arrows. The structure of 2-bromo-2methylpropane is not
required.
[4]
(ii). Explain why 2-bromo-2-methylpropane is the major product of this reaction.
……………………………………………………………………………………………………………………..
……………………………………………………………………………………………………………………..
……………………………………………………………………………………………………………………..
[2]
M/J-18-21
Q31. Most vehicle fuels contain hydrocarbons obtained from crude oil.
(a). (i). State the name of the type of reaction that hydrocarbons undergo when
being used as fuels.
………………………………………………………………………………………………………………………
[1]
(ii). Write an equation for the reaction of octane, C8H18, as a fuel, as in (a)(i).
………………………………………………………………………………………………………………………
[2]
(b). The supply of material suitable for use as fuels directly from crude oil is not sufficient
to meet demand. A process is carried out to make some of the larger hydrocarbon
molecules more useful.
(i). Name this process.
………………………………………………………………………………………………………………………
[1]
KAMRAN SHAHZAD 105

As well as producing fuels, this process produces compounds suitable for use in the
production of polymers. An example of such a compound is but-2-ene,
CH3CH=CHCH3.
(ii). Draw the repeat unit of the polymer that is produced from but-2-ene.
[2]
(iii). Name the type of polymerization that occurs during the production of the
polymer in (ii).
………………………………………………………………………………………………………………………
[1]
M/J-18-22
Q32. One reason for the wide variety of organic compounds is isomerism, either structural
isomerism or stereoisomerism.
(a). (i). Explain the meaning of the term structural isomerism.
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
[2]
(ii). Explain the meaning of the term stereoisomerism.
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
[2]
(b). Pent-1-ene, CH2=CH(CH2)2CH3, does not show stereoisomerism.
(i). Give two reasons why pent-1-ene does not show stereoisomerism.
Reason 1 …………………………………………………………………………………………………….
…………………………………………………………………………………………………….
Reason 2 …………………………………………………………………………………………………….
KAMRAN SHAHZAD 106

…………………………………………………………………………………………………….
[2]
(ii). A structural isomer of pent-1-ene is used as the monomer to form a polymer.
The repeat unit of this polymer is shown.
Draw the displayed formula of the monomer used to make this polymer.
Give the name of the monomer.
[2]
(iii). A different structural isomer of pent-1-ene shows geometrical isomerism.
Draw the structure of one of the two geometrical isomers with the formula
C5H10. Give the full name of this isomer.
KAMRAN SHAHZAD 107

[2]
M/J-18-23
Q33. (a). (i). Methylpropene can be polymerized to form a poly(alkene).
State the type of polymerization and draw the repeat unit of the polymer
formed from methylpropene.
Type of polymerization ……………………………………………………………………………………
Repeat unit
[3]
(ii). State the difficulty associated with the disposal of poly(alkenes).
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
[1]
O/N-17-22
Q34. (a). The hydrocarbons A, C4H10, and B, C4H8, are both unbranched.
A does not decolourise bromine.
B decolourises bromine and shows geometrical isomerism.
(i). Draw the skeletal formula of A.
KAMRAN SHAHZAD 108

[1]
(ii). The hydrocarbon A, C6H10, has a branched isomer.

Suggest why unbranched A has a higher boiling point than its branched
isomer.
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
[2]
(iii). Give the structural formula of B.
……………………………………………………………………………………………………………………….
[1]
(iv). Explain why B shows geometrical isomerism.
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
[2]
(v). Draw the mechanism of the reaction of B with bromine, Br2.
Include all necessary charges, dipoles, lone pairs and curly arrows.
KAMRAN SHAHZAD 109

[4]
(vi). Explain the origin of the dipole on Br2 in this mechanism.
……………………………………………………………………………………………………………………….
……………………………………………………………………………………………………………………….
[1]
M/J-17-22
Q35. Combustion data can be used to calculate the empirical formula, molecular formula and
relative molecular mass of many organic compounds. Combustion data cannot distinguish
between different structural isomers.
(a). Define the term structural isomers.
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
…………………………………………………………………………………………………………………………………..
[2]
(b). P is a hydrocarbon, CxHy. A gaseous sample of P occupied a volume of 25 cm3 at 37oC
and 100 kPa.
The sample was completely burned in 200 cm3 of oxygen (an excess).
The final volume, measured under the same conditions as the gaseous sample so that
the water produced is liquid and its volume can be ignored), was 150 cm 3.
Treating the remaining gaseous mixture with concentrated alkali, to absorb carbon
dioxide, decreased the volume to 50 cm3.
The equation for the complete combustion of P can be represented as shown.
(i). Use the data given to calculate the value of x.
KAMRAN SHAHZAD 110

x = ………………………………………..
[1]
(ii). Use the data given to calculate the value of
= ………………………………………………
[1]
(iii). Give the molecular formula and the empirical formula of P.
Molecular formula of P ……………………………………………………………………………………
Empirical formula of P …………………………………………………………………………………….

[2]
(iv). P is unbranched.
Give the skeletal formulae for two possible structure of P that are positional
isomers of each other.
KAMRAN SHAHZAD 111

[2]
(v). Use the general gas equation to calculate the mass of P present in the original
25 cm3 gaseous sample, which was measured at 37oC and 100 kPa.
Give your answer to three significant figures.
Mass = ………………………………….. g
[3]
M/J-17-23
Q36. A, B and C all have the formula C4H8. They all decolourise bromine and are structural isomers
of each other.
(a). State the name of the process by which A, B and C could be obtained from C10H22
…………………………………………………………………………………………………………………………………..
[1]
(b). Draw the structures of these three structural isomers.
[1]
(c). Only A shows geometrical isomerism.

(i). Explain the meaning of the term geometrical isomerism.
KAMRAN SHAHZAD 112

………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
[2]
(ii). Draw the displayed formula of A and use it to show the mechanism of the
reaction of A with HBr. Include all necessary charges, dipoles, lone pairs and
curly arrows.
[4]
(d). B does not show geometrical isomerism.
B react with HBr to form a mixture of two structural isomers, X and Y.
(i). State the meaning of the term chiral centre.
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
………………………………………………………………………………………………………………………..
[1]
(ii). Name B.
………………………………………………………………………………………………………………………..
[1]
(iii). X exists as a pair of optical isomers.

Draw these isomers using the conventional three-dimensional representation
KAMRAN SHAHZAD 113

[2]
(iv). Explain why X is produced in higher yield than Y.
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
………………………………………………………………………………………………………………………
[2]
(e). C does not show geometrical isomerism.
C reacts with HBr to form a mixture of two structural isomers, neither of which has a
chiral centre.
(i). Name C.
………………………………………………………………………………………………………………………
[1]
(ii). Draw the displayed formula of each of the structural isomers produced by the
reaction of C with HBr.
[2]
KAMRAN SHAHZAD 114

M/J-17-23
ANSWER SHEET
1. (a). (i). 4-methylhex-2-ene [1]
(ii). (Molecules with the) same structural formula (and same molecular formula) with different
arrangement of atoms/groups (in space) [1]
(iii). 4 [4]
Double-bond/alkene
(2) different groups on each double-bonded carbon
(one) chiral carbon (centre)/(one) carbon atom has 4 different groups attached/is a symmetric/is chiral
(b). (i). 2, 3-dimethylbut-2-ene [1]
(ii). [1]
(iii). Propanone [1]

(iv). [1]
(c). (i). (2-) methylprop(-1-)ene [1]

(ii). [4]
KAMRAN SHAHZAD 115

(iii). (tertiary carbocation)/(tertiary) intermediate is /C+ with least number of hydrogen atoms bonded to
it is more stable (than primary)
due to (positive) inductive effect of three/more methyl groups (cf one)/three/more electron rereleasing
methyl groups
reducing charge (density) on C+ [3]
2. (a). [1]
(b). [1]
(c). [2]
(d). [3]
3. (a). (i). vaporize/boil/turn to gas [1]

(ii). increasing molecular size/no of carbon atoms per molecule/length of carbon chain [1]
(iii). increasing b.pt/decreasing volatility [2]
increasing viscosity
increasing density
increasing depth of colour
decreasing flammability/decreasing ‘cleanliness’ of flame owtte
(b). (i). [1]
(ii). ethene use = making polythene/plastic/polymers [4]
feature of ethene = double bond/unsaturated
octane/alkane use = fuel/petrol
feature of octane/alkane = flammability/releases energy when burned/combusted
4. (a). (i). structural isomers: (different molecules with) same molecular formula [1]
But different structural formulae
Chiral: has a carbon/C attached to 4 different groups/atoms/chains OR has no plane/line of
symmetry/has non-superimposable mirror images. [1]
KAMRAN SHAHZAD 116

(ii). [4]
(b). (i). [1]
(ii). [1]
(iii). global dimming/PAN/smog/global warming [1]

(c). (i). (free) Radical substitution [1]
(ii). [5]
5. (a). (i). [3]
(ii). UV/High T/sunlight [1]

(iii). [5]
6. (a). [4]
(b). (i). (different molecules with) the same (molecular and) structural formula
KAMRAN SHAHZAD 117

Different arrangements of atoms (in space)/different displayed formula [2]
(ii). [2]
(c). reagent; NaBH4 or LiA/H4 or names [2]

Product; propan-2-ol
7. (a). (i). alkanes or paraffins not hydrocarbons
(ii). [2]
(b). (i). carbon allow graphite
(ii). [2]
(c). (i). from methane to butane

there are more electrons in the molecule
therefore greater/stronger van der Waals’ forces [2]
(ii). straight chain molecules can pack more closely

therefore, stronger van der Waals’ forces
or reverse argument [2]
8. (a). high temperature (above 450 oC)

use of a catalyst [2]
(b). [1]
(c). (i). electrophilic addition
(ii). dipole on Br2 clearly shown by δ + and δ - [6]
curly arrow from π bond of CH2 = CH2 to Brδ +
formation of carbocation
9. (a).
KAMRAN SHAHZAD 118

H atoms must be shown.

Structure must not contain any CH3 groups [1]
(b). [2]
10. (a). (i). [2]
(ii). [2]
(b). (i). hydrogen

nickel catalyst – allow platinum or palladium
(ii). isomer formed must be 1,2-dibromoethane (D above)
because
cis isomer has one Br atom on each carbon atom
mark is for the reason but wrong isomer is penalised [3]
11. (a). (i).
[6]
(ii). CH3/methyl radical [1]
(b).
KAMRAN SHAHZAD 119

[5]
12. (a).
[3]
13. (a). (i). order of atoms must be C-C-O [2]
Linear
(ii). a molecule or atom with an unpaired electron or
a species formed by the homolytic fission of a covalent bond
(iii). molecule has 2 bond pairs and one lone pair

and one unpaired electron
these may be shown in a diagram [3]
14. (a). (i). a compound which contains only carbon and hydrogen
(ii). separation of compounds by their boiling points [2]
(b). (i). high temperature and high pressure
high temperature and catalyst
(ii).
[3]
(c). (i).
KAMRAN SHAHZAD 120

[3]
15. (a). (i). CH3(CH2)7CHO

OHC(CH2)7CX
(ii). 2,4-dinitrophenylhydrazine
yellow/orange/red precipitate
16. (a). [1]
(b). (i). step 1 electrophilic

addition
Step 2 elimination or dehydrohalogenation
(ii). reagent NaOH/KOH/OH-
conditions in alcohol/ethanol
only allow conditions mark if reagent is correct [5]
(c). (i). Q is CH3CHO (as minimum)

R is CH3CO2H (as minimum)
(ii). step 3 is addition
step 4 is oxidation/redox [4]
17. (a). (i). break large hydrocarbons into smaller hydrocarbons or [2]
break down large hydrocarbons
smaller hydrocarbons are more useful or
smaller hydrocarbons are more in demand
(ii). using high temperature/thermal cracking or [1]
using catalysts/catalytic cracking
(iii). [1]
18. (a). (i). [2]
KAMRAN SHAHZAD 121

(ii). [2]
(iii). [3]
19. (a).
KAMRAN SHAHZAD 122

[5]
20. (a). high temperature and high pressure

high temperature and catalyst [2]
(b). [1]
(c).
[4]
(d). (i).
KAMRAN SHAHZAD 123

(ii). compound B
compound C [3]
(e).
allow any orientation of CH3 – groups [1]
(f).
[3]
21. (a). (i).

(ii). elimination or dehydration
(iii). phosphoric acid or concentrated sulfuric acid
Sulfuric acid must be ‘concentrated’ [3]
(b).
[4]
(c). (i). C6H10 [1]
(ii). [1]
KAMRAN SHAHZAD 124

(iii). electrophilic [2]
addition
(iv). [1]
22. (a). (i). alkanes or paraffins not hydrocarbons
(ii). [2]
(b). (i). carbon
carbon monoxide
(names required)
(ii). CO is toxic or affects or combines with hemoglobin
or carbon causes respiratory problems
(iii).
[4]
23. (a).
[2]
(b).
[2]
(c). (i). from methane to butane

there are more electrons in the molecule
therefore greater/stronger van der Waals’ forces
(ii). straight chain molecules can pack more closely
therefore, stronger van der Waals’ forces
or reverse argument [4]
24. (a). 117o to 120o [1]

(b). (i). electrophilic addition
(ii).
KAMRAN SHAHZAD 125

1 mark for each correct structure

allow correctly drawn optical isomers of the first structure [4]
25. (a). (i).
(ii).
[2]
26. (a). [2]
(b). (i). [2]
(ii). 109.5o AND 120o (117o – 122o) [1]

(iii). ethane = tetrahedral
ethene = trigonal planar [1]
(iv). [1]
(c). (i). [5]
(ii). [1]
27. (a). decolourisation with an alkene at room conditions/quickly/easily/
KAMRAN SHAHZAD 126

OR alkane needs higher temp/UV/is slow at room conditions
double/π/pi bond/C=C present in alkenes [2]
(b). (i). UV light/sunlight/high temperature [1]
(ii). (Free) radical
substitution [2]
(iii). [1]
(iv). [1]
(c). (i). electrophilic

addition [2]
(ii).
[4]
28. (a). (i). addition [1]

(ii). [1]
(iii). molecule unreactive/inert [1]

(iv). non-biodegradable [2]
creates toxic/harmful gases/HF/CO2/CO if burnt
29. (a). different (hydrocarbon) molecules have different numbers of electrons [1]
so different strengths/numbers/amount of VdW/IMFs/id-id [1]
(b). produces more useful/more valuable/higher demand substances/alkanes/alkenes [1]
(c). (i). [1]
(ii). addition polymerization [1]

(iii). [2]
(iv).
KAMRAN SHAHZAD 127

correct monomer [1]

fully displayed [1]
30. (a). (i).
curly arrow from C=C to H [1]

correct dipole on HBr and curly arrow from bond of HBr to Br [1]
tertiary intermediate cation [1]
-
Br wit curly arrow from lone pair [1]
(ii). (carbo)cation/tertiary ion/tertiary intermediate (more) stable (than primary) [1]
due to electron-releasing/(positive) inductive effect of more alkyl/methyl groups [1]
31. (a). (i). combustion [1]

(ii).
correct species [1]
correct balancing [1]
(b). (i). cracking [1]
(ii).
even number of C’s in correct backbone with ‘end bonds’ AND no C=C [1]
CH3 and H on each of two C drawn for 1 repeat unit only AND all the carbons must be tetravalent [1]
(iii). addition [1]
32. (a). (i). (molecules/isomers with) the same molecular formula/same number of atoms of each element [1]
different structural formulae/different structures [1]
(ii). (Molecules/isomers) with the same (molecular and) structural formula [1]
different arrange of atoms in space/different spatial arrangement of atoms. [1]
(b). (i). two Hs on one of the C=C carbons/terminal C/C-1 [1]
no chiral C/no C with 4 different groups/atoms/chains attached has a super(im)possible mirror image
KAMRAN SHAHZAD 128

[1]
(ii). [1]
2-methylbut-1-ene [1]
(iii). structure [1]
Trans-pent-2-ene or cis-pent-2-ene [1]

or E- or Z-
33. (a). (i). addition [1]
[2]
(ii). not/non- biodegradable/harmful combustion products [1]
34. (a). (i). [1]

(ii). (A/straight chain) has strong(er) (temporary dipole-) induced dipole (attractions) ora [1]
Because A/straight chain has) bigger (surface) area/more (points of) contact (in unbranched isomer) ora
OR
(so) more energy required to break the intermolecular forces ora [1]
(iii). [1]
(iv). No rotation/restricted/limited rotation of C=C/(carbon)double bond [1]
One (of the two) methyl groups/one (of the two) H (atoms) is on each C (of C=C) [1]
(v).
[1]
KAMRAN SHAHZAD 129

Dipole on Br2 in correct orientation AND arrow from the Br-Br bond to the Brδ -
[1]
correct carbocation/bromonium ion from the structure with C=C drawn [1]
Br- with lone pair, negative charge AND arrow from lone pair to the carbon atom of intermediate
OR
Using both arrows shown (in alternative diagram) [1]
(vi). electrons in pi bond induce it (the dipole) OR [1]
(high) electron density in pi bond/double bond/C=C repels electros (away from nearest Br)
OR
polarized by (high) electron density in pi bond/double bond/C=C
35. (a). (molecules/isomers with) the same molecular formula/same number of atoms of each element [1]
different structural/displayed formulae/different arrangement of bonds [1]
(b). (i). 4 [1]
(ii). 6 [1]
(iii). molecular = C4H8 [1]
empirical = CH2 [1]
using alternative supplied data
molecular = C2H12
empirical = CH2
(iv). [1]
[1]
(v). [1]
[1]
[1]
36. (a). cracking [1]

(b). [1]
KAMRAN SHAHZAD 130

(c). (i). (different) molecules with the same (molecular and) structural formula [1]
(due to) different arrangement in space caused by C=C/double bond [1]
(ii). [1]
dipole on H-Br in correct orientation AND arrow from the H-Br bond to the Brδ - [1]
correct carbocation from the structure with C=C drawn [1]

-
Br with lone pair, negative charge AND arrow from lone pair to the positively charged carbon atom of
intermediate [1]
(d). (i). a (tetrahedral) atom with four different groups/atoms/substituents attached [1]
OR
a carbon (atom) with four different groups/atoms/substituents attached
(ii). but – 1 – ene [1]
(iii).
[1]
second structure either mirror of first OR all bonds drawn the same with position of two groups
swapped. [1]
(iv). intermediate/(secondary carbo) cation from X is more stable ora [1]
OR
charge density of C+ (of the intermediate of X) is reduced
(due to) electron-releasing character/(positive) inductive effect of alkyl groups/ [1]
/due to electron releasing alkyl group
(e). (i). (2- ) methylpropene/(2- ) methylprop- 1- ene [1]
(ii). [2]
KAMRAN SHAHZAD 131

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Worksheet#13 As Hydrocarbons

A. H2 gas, nickel catalyst, 400oC

Number of moles Number of moles

W ‘Bromine reacts with alkanes by electrophilic substitution.’

X ‘Bromine reacts with alkenes by a free-radical addition mechanism.’

Y ‘Alkenes can be oxidised by acidified manganite (VII) ions.’

Z ‘Alkenes are formed from alkanes by cracking.’

Which two students are correct?

A. W and X B. W and Z C. X and Y D. Y and Z

What is the formula of the hydrocarbon?

Reaction mechanism Organic product

Q9.Corticosterone is a hormone involved in the metabolism of carbohydrates and proteins.

How many chiral centres are there in one molecule of corticosterone?

Which diagram correctly shows methyl methylpropenoate?

Q12. In this question, structural isomerism and stereoisomerism should be considered.

How many isomeric aldehydes have the formula C5H10O?

Q14. β-carotene is responsible for the orange colour of carrots.

β-carotene is oxidised by hot, concentrated, acidified KMnO4.

How many of these product molecules contain a ketone functional group?

Which of the students are correct?

It may be considered to be made by addition polymerization of CH2 = CH(OH).

Q18. The diagram shows the skeletal formula of phenazine.

What is the empirical formula of phenazine?

A. C6H4N B. C6 H 6 N C. C12H8N2D. C12H12N2

Q22. Artermisinin is a powerful anti-malarial drug.

How many chiral centres are there in each molecule of artemisinin?

Q29. Pent-2-ene, CH3CH2CH = CHCH3, reacts in a similar way to ethane.

Pent-2-ene is reacted with cold, dilute, acidified manganite (VII) ions.

What will be produced in the greatest amount?

Which structure represents the repeat unit in poly (prop-2-en-1 –ol)?

A. It has a negative change

Which diagram correctly illustrates an optically active ‘trans fat’?

Sorbic acid will react with

 Hydrogen in the presence of a nickel catalyst.

moles of hydrogen moles of bromine

In a propagation step a free radical is formed

How many different forms of are possible?

A. The carbon-carbon bond is longer and stronger in poly (ethane).

How many σ and π bonds are present in this molecule?

How many chiral center are there in one molecule of menthol?

Q42. But-2-ene- 1, 4-diol is converted in two steps through an intermediate X into

What could be the reagent for step 1 and the intermediate X?

reagent for step 1 X

A cold acidified KMnO4 OHCH2CH2CH(OH)CH2OH

B hot acidified KMnO4 OHCCH(OH)CH2CHO

What is the value of n?

Q44. High-energy radiation in the stratosphere produces free-radicals from chlorofluoroalkanes,

Which free-radical is most likely to result from the irradiation of CHFClCF2Cl?

Q45. Isomers X and Y both react with HBr.

A mixture of X and Y is reacted with HBr.

A. (CH3)2CHCBr3 (CH3)2CBrCHBr2 CH3CHBrCHBrCH3

Which combination of compounds W, X, Y and Z can be obtained?

CH2 = CH2 CH3CH = CH2 CH3CH2CH3 CH2 = CHCH = CH2

Q48. Use of the Data Booklet is relevant to this equation.

Q49. The molecule shown in optically active.

How many chiral carbon atoms are present in this molecule?

If this compound is reacted with a cold, dilute, acidified solution of potassium

Which reagents could achieve this transformation in the laboratory?

Which information about this reaction is correct?