1.	Which of the following are isomers of pentane?
I.	2-methylpentane
II.	methylbutane
III.	dimethylpropane
A.	I and II only
B.	I and III only
C.	II and III only
D.	I, II and III
(Total 1 mark)

2.	State and explain whether the following molecules are primary, secondary or tertiary halogenoalkanes.
E:

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F:

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G:

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(Total 4 marks)

3.	Alkenes are important starting materials for a variety of products.
(a)	State and explain the trend of the boiling points of the first five members of the alkene homologous series.
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(3)
 
(b)	Describe two features of a homologous series.
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(2)
(Total 5 marks)

4.	Which of the following pairs are members of the same homologous series?
A.	CH3CH2CH2OH and CH3CH2CHO
B.	CH3CH(OH)CH3 and CH3CH2CH(OH)CH3
C.	CH3COCH3 and CH3CH2COOH
D.	CH3COCH2CH3 and CH3CH2CHO
(Total 1 mark)

5.	Which is the correct classification of these alcohols?

		1	2	3

	1	2	3	
A.	tertiary	secondary	primary	
B.	tertiary	primary	secondary	
C.	tertiary	tertiary	secondary	
D.	secondary	primary	secondary	
(Total 1 mark)

6.	What is the IUPAC name for CH3CH2CH(CH3)CH3?
A.	1,1-dimethylpropane
B.	2-ethylpropane
C.	2-methylbutane
D.	3-methylbutane
(Total 1 mark)

7.	What is the IUPAC name of the following compound?
		
A.	2-methylbutane
B.	Ethylpropane
C.	3-methylbutane
D.	Pentane
(Total 1 mark)

8.	(a)	The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 °C, but not necessarily in that order.

(i)	Identify the boiling points for each of the isomers A, B and C and state a reason for your answer.

Isomer	A	B	C	
Boiling point				
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(3)
 
(ii)	State the IUPAC names of isomers B and C.
B: .......................................................................................................................
C: .......................................................................................................................
(2)
 
(b)	Both C5H12 and C5H11OH can be used as fuels. Predict which compound would release a greater amount of heat per gram when it undergoes complete combustion. Suggest two reasons to support your prediction.
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(3)
(Total 8 marks)

9.	The following is a computer-generated representation of the molecule, methyl 2-hydroxy benzoate, better known as oil of wintergreen.

(i)	Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full structural formula, including any multiple bonds that may be present.
The computer-generated representation shown does not distinguish between single and multiple bonds.
(2)
 
(ii)	In this representation, two of the carbon-oxygen bond lengths shown are 0.1424 nm and 0.1373 nm. Explain why these are different and predict the carbon-oxygen bond length in carbon dioxide.
(2)
 
(iii)	Name all the functional groups present in the molecule.
(2)
(Total 6 marks)

10.	Explain, using equations, the following steps in the free-radical mechanism of the reaction of methane with chlorine.
•	Initiation
•	Propagation
•	Termination
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(Total 4 marks)

11.	Which of the structures below is an aldehyde?
A.	CH3CH2CH2CH2OH
B.	CH3CH2COCH3
C.	CH3CH2COOCH3
D.	CH3CH2CH2CHO
(Total 1 mark)

12.	Which substances are possible products of the incomplete combustion of octane?
A.	Carbon dioxide and hydrogen gas
B.	Carbon monoxide and water vapour
C.	Carbon monoxide and hydrogen gas
D.	Methane and hydrogen gas
(Total 1 mark)

13.	Which equations represent the incomplete combustion of methane?
I.	CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)
II.	CH4(g) + 1½O2(g) → CO(g) + 2H2O(g)
III.	CH4(g) + O2(g) → C(s) + 2H2O(g)
A.	I and II only
B.	I and III only
C.	II and III only
D.	I, II and III
(Total 1 mark)

14.	(i)	State and explain the trend in the boiling points of the first six alkanes involving straight-chains.
(2)
(ii)	Write an equation for the reaction between methane and chlorine to form chloromethane. Explain this reaction in terms of a free-radical mechanism.
(5)
(Total 7 marks)

15.	Which of the following statements about alkenes is not correct?
A.	They have reactive double bonds.
B.	They can form addition polymers.
C.	They react mainly by substitution.
D.	They can react with water to form alcohols.
(Total 1 mark)

16.	Below is a schematic diagram representing some reactions of ethene. The letters A–D represent the organic compounds formed from the reactants and catalysts shown.

	Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC name of compound C.

A:

B:

C:

IUPAC name: ..............................................................................................................

D:

(Total 5 marks)

17.	(i)	Describe a chemical test that could be used to distinguish between propane and propene. In each case state the result of the test.
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(2)

(ii)	Under certain conditions propene can polymerize to form poly(propene). State the type of polymerization taking place and draw a section of the polymer to represent the repeating unit.
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(2)
 
(iii)	Other than polymerization, state one reaction of alkenes which is of economic importance.
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(1)
(Total 5 marks)

18.	What organic product is formed in the following reaction?
		(CH3CH2)CH=CH(CH2CH3) + H2O 
A.	CH3(CH2)2CH(OH)CH2CH3
B.	CH3(CH2)5CH3
C.	CH3(CH2)2CH(OSO3H)CH2CH3
D.	CH3(CH2)6OH
(Total 1 mark)

19.	Which products can be potentially obtained from crude oil and are economically important?
	I.	Plastics
II.	Margarine
III.	Motor fuel
A.	I and II only
B.	I and III only
C.	II and III only
D.	I, II and III
(Total 1 mark)

20.	Two compounds, A and D, each have the formula C4H9Cl.
	Compound A is reacted with dilute aqueous sodium hydroxide to produce compound B with a formula of C4H10O. Compound B is then oxidized with acidified potassium manganate(VII) to produce compound C with a formula of C4H8O. Compound C resists further oxidation by acidified potassium manganate(VII).
	Compound D is reacted with dilute aqueous sodium hydroxide to produce compound E with a formula of C4H10O. Compound E does not react with acidified potassium manganate(VII).
	Deduce the structural formulas for compounds A, B, C, D and E.

A:

B:

C:

D:

E:

(Total 5 marks)

21.	(a)	(i)	Below are four structural isomers of alcohols with molecular formula C4H10O.
State the name of each of the isomers A, B, C and D.

(4)
 
(ii)	Determine the isomer that cannot be oxidized by acidified potassium dichromate(VI), K2Cr2O7.
(1)
 
(iii)	Determine the isomer which can be oxidized to butanal.
(1)
 
(iv)	Determine the isomer which can be oxidized to butanone.
(1)
 
(v)	Suggest the structural formula of another isomer of C4H10O.
(1)
 
(b)	(i)	Isomer A is formed by reacting 1-bromobutane with aqueous sodium hydroxide.
State whether the reaction would proceed via an SN1 or SN2 mechanism.
(1)
 
(ii)	Explain the mechanism named in part (b) (i) using curly arrows to represent the movement of electron pairs.
(3)
(Total 12 marks)

22.	(i)	Deduce the structural formulas of the two alcohol isomers of molecular formula C3H8O. Name each isomer and identify each as either a primary or a secondary alcohol.
(3)
 
(ii)	Oxidation of the alcohol isomers lead to the formation of different organic products.
Determine the structures of the organic products formed from the oxidation of each alcohol isomer in (i) above and list the conditions required to obtain the different products.
(5)
(Total 8 marks)

23.	What is the type of mechanism and an important feature of the reaction between C(CH3)3Br and aqueous NaOH?

	Mechanism	Feature	
A.	SN1	a transition state	
B.	SN1	an intermediate	
C.	SN2	a transition state	
D.	SN2	an intermediate	
(Total 1 mark)

24.	2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.
Explain the mechanism by using curly arrows to represent the movement of electron pairs.

(Total 4 marks)

25.	Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts with aqueous sodium hydroxide, NaOH(aq)?
A.	Addition
B.	Free-radical substitution
C.	SN1
D.	SN2
(Total 1 mark)

26.	Halogenoalkanes can undergo SN1 and SN2 reactions with aqueous sodium hydroxide.
Which halogenoalkane will react fastest with a 0.1 mol dm–3 solution of aqueous sodium hydroxide?
A.	2-chloro-2-methylpropane
B.	2-iodo-2-methylpropane
C.	1-chlorobutane
D.	1-iodobutane
(Total 1 mark)

27.	(i)	Chloroethene can be converted to ethanol in two steps. For each step deduce an overall equation for the reaction taking place.
	Step 1:
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	Step 2:
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(2)
 
(ii)	State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the laboratory.
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(2)
 
(iii)	State an equation, including state symbols, for the reaction of ethanoic acid with water. Identify a Brønsted-Lowry acid in the equation and its conjugate base.
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(3)
(Total 7 marks)

28.	But-2-ene can be converted to butan-2-one in two stages.
(i)	Draw the structural formulas of but-2-ene and butan-2-one.
(2)
 
(ii)	Deduce a reaction pathway for the two stages of the reaction. Your answer should include the fully balanced equation for each stage of the reaction and the reagents and conditions for the two stages.
(5)
(Total 7 marks)