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NOTE: You are strongly advised to adhere to the suggested time allocation for each question. Some of the questions may require integration of knowledge from previously learnt topics.

2012 Edition

Section A: Multiple Choice [15 minutes per 10 questions] 1 10 cm3 of a hydrocarbon was completely burnt in 100 cm3 of oxygen. The volume of the residual gas obtained was 80 cm3. When the residual gas was shaken with aqueous sodium hydroxide, the volume decreased to 20 cm3. Which one of the following could have been the formula of the hydrocarbon? (All volumes were measured at room temperature and pressure.) A 2 C6H6 B C6H8 C C6H10 D C6H12

How many stereoisomers does the compound below exhibit?

Cl Br


2 optical isomers 2 geometric isomers 4 optical isomers and 4 geometric isomers no stereoisomers

The general structure of an oestrone molecule is given below.



How many chiral centres are there in the molecule? A 1 B 2 C 3 D 4

How many isomers are possible for the unsaturated compound of molecular formula C3H5F? A 3 B 4 C 5 D 6

An energy level diagram for a single reaction step is shown below. energy

reactant reaction path To which of the following steps in the reaction of methane with chlorine in the presence of light does this diagram apply? A B CH2Cl + Cl2 CH3 + CH3 CH2Cl2 C2H6 + Cl

C D 6

CH3 Cl2

Cl Cl

CH3Cl Cl

When alkane T, C7H16, was reacted with bromine under ultraviolet light, it produced only three isomeric monobromo compounds, with the formula C7H15Br. What is the likely identity of alkane T? A B CH3(CH2)5CH3 (CH3)2CH(CH2)3CH3 C D (CH3)3CCH2CH2CH3 (CH3)3CCH(CH3)2

Compound A has the structural formula shown below: CH3CHCH=CH2 CH2CH2CH3 Which of the following statements regarding compound A is correct? A B C D It exhibits cis-trans isomerism. It has no optical activity. It decolourises hot acidified KMnO4. Its IUPAC name is 2-propylbut-1-ene.

Trichloroethene, Cl2C=CH(Cl), is widely used as a dry-cleaning agent. With which of the following does trichloroethene react to give a chiral product? A H2 B Br2 C HCl D H2SO4

Which one of the following structures will have cis-trans isomers? A B CH3BrC=CCl2 C D CH2=CHCH2CH=CH2 C6H5CH=CHCOOH

10 Which hydrocarbon, on treatment with hot acidified potassium manganate(VII), would give only one acid as the only product? A CH3CH=CH2 B CH3CH=CHCH3 C CH3CH2CH=CHCH3 D (CH3)2C=CHCH3

11 When ethene reacts with bromine in the presence of concentrated aqueous sodium nitrate, the product contains the following compound. H H C H C H

ONO2 Br What is the intermediate formed in this reaction? H A H C H C Br H C H H C ONO2 H C H



H C Br H

12 Ethene is shaken with an aqueous mixture of bromine and sodium chloride. Which of the following compounds will not be formed? A C CH2BrCH2OH CH2BrCH2Br B D CH2BrCH2Cl CH2(OH)CH2Cl

13 When methylbenzene is treated with bromine in the presence of a catalyst, a mixture of two monobrominated isomers is formed. What are the structure of these two isomers?

CH3 Br


CH3 Br


Br Br CH2Br CH3 Br CH3 CH3

Br Br
14 Which of the following reagents may be used to distinguish between but-1-ene and but-2-ene? A B C D hydrogen bromide aqueous bromine acidified potassium manganate(VII) alcoholic potassium hydroxide

15 1 mole of an organic compound P undergoes a reaction with alcoholic sodium hydroxide to form 2 moles of HBr. Which of the following could be P? A C

For each of the questions below, 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 which you consider to be correct). The responses A to D should be selected on the basis of A 1,2 and 3 are correct B 1 and 2 only are correct C 2 and 3 only are correct D 1 only is correct

No other combination of statements is used as a correct response.

16 Methane reacts with chlorine gas in the presence of ultraviolet light to form a mixture of products. The mechanism involved is that of free radical substitution. Which one of the following statements is true about the reaction? 1 2 3 CH3Cl is formed only in the propagation step. HCl is formed only in the propagation step. Homolytic cleavage occurs in the initiation step.

17 The C2H2 molecule is linear. What can be deduced from this about the molecule? 1 2 3 There are 3 and 2 bonds in the molecule. The carbon atoms are sp hybridised. There is no lone pair of electrons on the carbon atoms.

18 Which of the following statement(s) about benzene is/are correct? 1 2 3 The carbon atoms lie on the same plane. Each carbon-carbon bond is shorter than a carbon-carbon single bond. Each carbon-carbon bond is stronger than a carbon-carbon double bond.

19 A hydrocarbon, X, on heating with an excess of hot concentrated acidified potassium manganate(VII), produces HO2CCH2CH2CH2COCH3. What could X be?




20 The formulae of two halogenoalkanes are given below. C2H5Cl X C2H5Br Y

1 The van der Waals forces in X are stronger than those in Y. 2 The C-Cl bond is more polar than C-Br bond. 3 The C-Cl bond in X is harder to break than the C-Br bond in Y.

Section B : Structured/Essay Questions Question 1 [8 marks / 12 min] Chlorinated methanes are useful solvents in synthetic chemistry research. However, exposure to high concentrations can affect the central nervous system, degenerate the liver and kidneys and may result in coma and even death. a) State the reagent and conditions used to produce these substances from methane. b) i) Describe the reaction mechanism for the formation of chloromethane, CH3Cl , from methane. Provide appropriate labels for each step. [1] [3]

ii) Use the mechanism you have provided in (b)(i) to explain how polychlorinated methanes (eg. dichloromethane, CH2Cl2) can be formed from methane. [1] iii) The process in (b)(ii) also produces small quantities of chlorinated ethanes. Explain how this might arise. [1] c) Some standard enthalpy changes of formation are given: Hfo (CH4) = 75 kJmol1 Hfp (CH3Cl) = 82 kJmol-1 Hfo (HCl) = 92 kJmol1 Calculate the enthalpy change of formation of the following reaction: CH4(g) + Cl2(g) CH3Cl(g) + HCl(g) [2]

Question 2 [12 marks / 18 min] The structure of compound J is shown below:


H H C C Cl CH3

a) In the boxes below, draw the structures of the organic compounds expected to form when J reacts with each of the following: [5]


Br2(g) with Fe catalyst


alcoholic NaOH under reflux

iii) acidified KMnO4 under reflux

b) Compound J also reacts with a mixture of concentrated nitric and sulfuric acids at 60oC. i) State the mechanism of the reaction that occurs. [1] ii) Write equations to describe the mechanism of the reaction. You may use R to represent the group that does not take part in the reaction. [3] c) For the given pair of compounds, give one simple chemical test which would enable you to distinguish between them. You are to state the reagent(s) and conditions required, write balanced equations for any reactions that occur and the observation for each compound. [3] CH3CH=CH2 Reagent(s) & Condition Balanced Equation(s) Observation(s) CH3CH2CH3

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Answers to Selected Questions

(Note that answers to questions which have answers that can be found directly from the notes are NOT given.)

Section A 1 B 2 D 3 D 4 B 5 D

6 7 8 9 10


11 12 13 14 15


16 17 18 19 20


Section B 1. b) ii) Polychlorinated methanes are formed when the mono-chlorinated product is attacked by the Cl radical and undergoes the substitution process. iii) The chlorinated ethanes are formed when 2 chlorinated methyl radicals (eg. CH2Cl) collide in the termination step. c) Hr = 75 82 92 = 92 kJ mol1


a) i)


iii) . b) i) ii) electrophilic substitution formation of electrophile eqn for slow step leading to formation of intermediate with tetrahedral C eqn for fast step re-formation of aromatic ring [arrows showing electron movement are required]


Br2(g) or Br2(org solvent) / in the dark CH3CH=CH2 + Br2 CH3CH(Br)CH2Br decolourisation / no decolourisation [use of Br2(aq) accepted; eqn provided must reflect formation of bromoalcohol] [oxidation is also acceptable provided eqn and observation is correct]