ORGANIC SL

1. Which of the structures below is an aldehyde?

O O

A. C H 3C H 2C H C. C H 3C H 2C O H

O O

B. C H 3C C H 3 D. C H 3C O C H 3

(Total 1 mark)
2. What product results from the reaction of CH2==CH2 with Br2?

A. CHBrCHBr C. CH3CH2Br

B. CH2CHBr D. CH2BrCH2Br

(Total 1 mark)
3. What is the final product formed when CH 3CH2OH is refluxed with acidified potassium dichromate(VI)?

A. CH3CHO C. CH3COOH

B. CH2==CH2 D. HCOOCH3

(Total 1 mark)
4. Two reactions of an alkene, B, are shown below.

H 2
CH CH
C 4H 10 3 3 C 4H 9B r
A N i
C C C

H H
B

(i) State the name of A and write an equation for its complete combustion. Explain why the incomplete
combustion of A is dangerous.

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(5)
(ii) Outline a test to distinguish between A and B, stating the result in each case.

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(3)
(iii) Write an equation for the conversion of B to C. State the type of reaction taking place and draw the structure
of C.

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(3)
(Total 11 marks)
5. Which of the substances below is least soluble in water?

A. CH2OHCHOHCH2OH O

C. CH 3C H 2CO H
O

B. C H 3C C H 3 O

D. CH 3C O C H 3

(Total 1 mark)
6. (a) Halogenoalkanes undergo nucleophilic substitution reactions. The rates and mechanisms of these reactions
depend on whether the halogenoalkane is primary, secondary or tertiary. Explain the term nucleophilic
substitution.

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(2)
(b) The formula C4H9Br represents more than one compound. Using this formula, draw a structure (showing all
bonds between carbon atoms) to represent a halogenoalkane that is

(i) primary.

(1)
(ii) secondary.

(1)
(iii) tertiary.

(1)
(Total 5 marks)
7. Which substance(s) could be formed during the incomplete combustion of a hydrocarbon?

I. Carbon

II. Hydrogen

III. Carbon monoxide

A. I only C. I and III only

B. I and II only D. II and III only

(Total 1 mark)
8. Which formulas represent butane or its isomer?

I. CH3(CH2)2CH3

II. CH3CH(CH3)CH3

III. (CH3)3CH

A. I and II only C. II and III only

B. I and III only D. I, II and III

(Total 1 mark)
9. For the two compounds HCOOCH2CH3 and HCOOCHCH2:

I II

(i) State and explain which of the two compounds can react readily with bromine.

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(2)
(ii) Compound II can form polymers. State the type of polymerization compound II undergoes, and draw the
structure of the repeating unit of the polymer.

(2)
(Total 4 marks)
10. Identify which of the compounds butane, chloroethane, propanone and propan-1-ol are

(i) insoluble in water and give your reasoning.

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(2)
(ii) water soluble and give your reasoning.

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(2)
(Total 4 marks)
11. Which statement about neighbouring members of all homologous series is correct?

A. They have the same empirical formula.

B. They differ by a CH2 group.

 C. They possess different functional groups.

D. They differ in their degree of unsaturation.

(Total 1 mark)
12. What is the IUPAC name for CH3CH2CH(CH3)2?

A. 1,1-dimethylpropane

B. 2-methylbutane

C. isopentane

D. ethyldimethylmethane

(Total 1 mark)
13. The compound C2H4 can be used as a starting material for the preparation of many substances.

(a) Name the compound C2H4 and draw its structural formula.

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(2)
(b) In the scheme below, state the type of reaction and identify the reagent needed for each reaction.

A B
C2H4 → CH3CH2OH → CH3COOH

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(4)
(c) C2H4 can be converted into one of the compounds below in a single step reaction.

C2H3Cl C2H4Cl2

Draw the structural formula for each of these compounds and identify the compound which can be formed
directly from C2H4.

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(3)
(d) One of the two compounds in (c) has an isomer. Draw the structural formula of the isomer and explain why it
can not be formed directly from C2H4.

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(2)
(e) C2H4 can also react to form a polymer. Name this type of polymer and draw the structural formula of a
section of this polymer consisting of three repeating units.

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(2)
(f) Polymers can also be formed in a different type of reaction. Identify this type of reaction and name two
different types of such polymers.

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(3)
(Total 16 marks)
14. Which product is formed by the reaction between CH2CH2 and HBr?

A. CH3CH2Br C. BrCHCHBr

B. CH2CHBr D. CH3CHBr2

(Total 1 mark)
15. Which reaction(s) involve(s) the formation of a positive ion?
–
I. CH3CH2CH2Br + OH

–
II. (CH3)3CBr + OH

A. I only C. Both I and II

B. II only D. Neither I nor II

(Total 1 mark)
16. Which compound has the lowest boiling point?

A. CH3CH2CH(CH3)CH3

B. (CH3)4C

C. CH3CH2CH2CH2CH3

D. CH3CH2OCH2CH3

(Total 1 mark)
17. What type of reaction does the equation below represent?

CH2=CH2 + Br2 → BrCH2CH2Br

A. substitution B. condensation
 C. reduction D. addition

(Total 1 mark)
18. The plastic PVC, poly(chloroethene), is made from the monomer chloroethene, C 2H3Cl, by a polymerization
reaction.

(i) Draw the structural formula of chloroethene.

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(1)
(ii) State the type of polymerization reaction that occurs to make poly(chloroethene) and identify the structural
feature needed in the monomer.

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(2)
(iii) Draw the structure of the repeating unit of poly(chloroethene).

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(1)
(iv) Explain why monomers are often gases or volatile liquids, whereas polymers are solids.

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(2)
(Total 6 marks)
19. Consider the following compounds.

I. CH3CH2CH(OH)CH3

II. CH3CH(CH3)CH2OH

III. (CH3)3COH

The compounds are treated separately with acidified potassium dichromate(VI) solution. Which will produce a
colour change from orange to green?

A. I and II only C. II and III only

B. I and III only D. I, II and III

(Total 1 mark)
20. Which compound is a member of the same homologous series as 1-chloropropane?

A. 1-chloropropene

B. 1-chlorobutane
 C. 1-bromopropane

D. 1,1-dichloropropane

(Total 1 mark)
21. Which formula is a correct representation of pentane?

A. CH3CH2CHCH2CH3 C. CH3(CH2)3CH3

B. (CH3CH2)2CH3 D. CH3(CH3)3CH3

(Total 1 mark)
22. Which statement is correct about the reaction between methane and chlorine?

–
A. It involves heterolytic fission and Cl ions.

B. It involves heterolytic fission and Cl· radicals.

–
C. It involves homolytic fission and Cl ions.

D. It involves homolytic fission and Cl· radicals.

(Total 1 mark)
23. Which formula is that of a secondary halogenoalkane?

A. CH3CH2CH2CH2Br C. (CH3)2CHCH2Br

B. CH3CHBrCH2CH3 D. (CH3)3CBr

(Total 1 mark)
24. Which compound is converted to butanal by acidified potassium dichromate(VI) solution?

A. butan-1-ol

B. butan-2-ol

C. butanone

D. butanoic acid

(Total 1 mark)
25. Methylbenzene, C6H5CH3, reacts with Cl2 to form different products depending on the conditions used. For the
gas-phase reaction of C6H5CH3 and Cl2 in ultraviolet light,

(a) draw a structural formula for the product C 7H7Cl.

(1)
(b) provide a stepwise mechanism, clearly labelling each step.

)
(c) explain the role of the ultraviolet light.

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(1)
(Total 7 marks)
26. How many structural isomers are possible with the molecular formula C 6 H14?

A. 4 B. 5 C. 6 D. 7
 (Total 1 mark)
27. Which compound is a member of the aldehyde homologous series?

A. CH3COCH3 C. CH3CH2COOH

B. CH3CH2CH2OH D. CH3CH2CHO

(Total 1 mark)
28. Ethene, propene and but-2-ene are members of the alkene homologous series.

(a) Describe three features of members of a homologous series.

(3)
(b) State and explain which compound has the highest boiling point.

(3)
(c) Draw the structural formula and give the name of an alkene containing five carbon atoms.

(2)
(d) Write an equation for the reaction between but-2-ene and hydrogen bromide, showing the structure of the
organic product. State the type of reaction occurring.

(3)
(e) Propene can be converted to propanoic acid in three steps:

step1 step 2 step 3

propene propan-1-ol propanal propanoic acid

State the type of reaction occurring in steps 2 and 3 and the reagents needed. Describe how the conditions of
the reaction can be altered to obtain the maximum amount of propanal, and in a separate experiment, to
obtain the maximum amount of propanoic acid.

(5)
(f) Identify the strongest type of intermolecular force present in each of the compounds propan-1-ol, propanal
and propanoic acid. List these compounds in decreasing order of boiling point.

(4)
(Total 20 marks)
–3
29. The hydrolysis of 2-iodo-2-methylpropane by 0.10 mol dm KOH(aq) to form 2-methylpropan-2-ol is an example
of nucleophilic substitution.

Give equations to illustrate the SN1 mechanism for this reaction.

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(Total 2 marks)
30. Which type of compound can be made in one step from a secondary alcohol?

A. an aldehyde C. a carboxylic acid

B. an alkane D. a ketone

(Total 1 mark)
31. Which formula represents a tertiary alcohol?
 A . C H 3 C H CH 2 C H 3 B. C H 3 CH C H 2 C H 2 O H

C H 2O H C H 3

C. CH 3 D . CH 3

CH 3 C CH 2 C H 3 CH 3 C H C H CH 3

O H O H

(Total 1 mark)
32. Which reaction type is typical for halogenoalkanes?

A. nucleophilic substitution C. electrophilic addition

B. electrophilic substitution D. nucleophilic addition

(Total 1 mark)
33. Which substance is not readily oxidized by acidified potassium dichromate(VI) solution?

A. propan-1-ol C. propanal

B. propan-2-ol D. propanone

(Total 1 mark)
34. The molecular formula C4H9Br represents four structural isomers, all of which can undergo nucleophilic
substitution reactions with aqueous sodium hydroxide. An equation to represent all these reactions is

C4H9Br + NaOH ® C4H9OH + NaBr

(a) Explain what is meant by the term nucleophilic substitution.(2)

(b) The main mechanism for a tertiary halogenoalkane is S N1. Give the equations for this substitution reaction of
the tertiary isomer of C4H9Br. Show the structures of the organic reactant and product and use curly arrows
to show the movement of electron pairs.(4)

(c) The main mechanism for a primary halogenoalkane is SN2. Give the mechanistic equation for this
substitution reaction of the straight-chain primary isomer of C 4H9Br, showing the structures of the organic
reactant and product, and using curly arrows to show the movement of electron pairs.(4)

(d) Give a structural formula for the secondary isomer and for the other primary isomer. State the name of each
isomer.(4)

(Total 14 marks)
35. What is the correct name of this compound?
C H 3

C H 3 C H CH 2 C H 2

C H 3

A. 1,3-dimethylbutane C. 2-methylbutane

B. 2,4-dimethylbutane D. 2-methylpentane

(Total 1 mark)
36. Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products are most likely to be
formed during this reaction?

A. Carbon monoxide and water B. Carbon monoxide and hydrogen

 C. Carbon dioxide and hydrogen D. Carbon dioxide and water

(Total 1 mark)
37. What is/are the product(s) of the reaction between ethene and hydrogen bromide?

A. CH3CH2Br C. CH2BrCH2Br

B. CH3CH2Br and H2 D. CH3BrCH2 Br and H2

(Total 1 mark)
38. (a) State two characteristics of a homologous series.

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(2)
(b) Describe a chemical test to distinguish between alkanes and alkenes, giving the result in each case.

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(3)
(Total 5 marks)
39. Write equations to show the mechanisms of the following reactions. In each case, show the structure of the
intermediate and organic product, and use curly arrows to show the movement of electron pairs.

(i) the reaction between KOH and CH3CH2CH2CH2Cl.

(3)
(ii) the reaction between KOH and (CH3)3CCl.

(2)
(Total 5 marks)
40. Which are characteristics typical of a free radical?

I. It has a lone pair of electrons.

II. It can be formed by the homolytic fission of a covalent bond.

III. It is uncharged.

A. I and II only C. II and III only

B. I and III only D. I, II and III

41. Some alcohols are oxidized by heating with acidified potassium dichromate(VI). If oxidation does occur, identify
 the possible oxidation products formed by each of the alcohols below. Indicate if no oxidation occurs.

Butan-1-ol

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Butan-2-ol

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2-methylpropan-2-ol

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(Total 4 marks)
42. Chlorine and ethane react together to form chloroethane.

(a) State the condition needed for the reaction to occur.

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(1)
(b) Write equations to represent initiation, propagation and termination steps in the reaction.

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(4)
(Total 5 marks)
43. Which of the following products could be formed from the oxidation of ethanol?

I. ethanal

II. ethanoic acid

III. ethane

A. I and II only C. II and III only

B. I and III only D. I, II and III

(Total 1 mark)
44. CH3COCH3 is the first member of the ketone homologous series. Draw the full structural formula of the next
member of this homologous series and predict how its melting point compares with that of CH 3COCH3.

(Total 2 marks)
45. What is the reaction type when (CH3)3CBr reacts with aqueous sodium hydroxide to form (CH3)3COH and NaBr?

A. Addition C. SN1

B. Elimination D. SN2

(Total 1 mark)
46. Which species is a free radical?

A. •CH3 + – D. :CH3
B. CH3 C. CH3

(Total 1 mark)
47. Which compound is a tertiary halogenoalkane?

A. (CH3CH2)2CHBr B. CH3(CH2)3CH2Br
 C. (CH3)2CHCH2CH2Br D. CH3CH2C(CH3)2Br

(Total 1 mark)
48. Which species reacts most readily with propane?

A. Br2 B. Br• – +
C. Br D. Br

(Total 1 mark)
49. (i) Write an equation for the reaction between but-2-ene and bromine, showing the structure of the organic
product.

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(2)
(ii) State the type of reaction occurring.

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(1)
(Total 3 marks)
50. CH3COCH3 can be prepared in the laboratory from an alcohol. State the name of this alcohol, the type of reaction
occurring and the reagents and conditions needed for the reaction.

(Total 5 marks)
51. 2-bromobutane can be converted into butan-2-ol by a nucleophilic substitution reaction. This reaction occurs by
two different mechanisms.

(i) Give the structure of the transition state formed in the SN2 mechanism.

(2)
(ii) Write equations for the SN1 mechanism.

(2)
(Total 4 marks)
52. Ethene is an unsaturated hydrocarbon used as a starting material for many organic chemicals.

(a) Draw the structural formula of ethene and state the meaning of the term unsaturated hydrocarbon.

(2)
(b) State an equation for the conversion of ethene to ethanol and identify the type of reaction.

(2)
(c) Describe the complete oxidation of ethanol and name the product. Include the conditions, reagents required
and any colour changes.

(4)
(d) State an equation for the reaction between ethanol and the product of complete oxidation in (c). Include any
other reagent required for this reaction. Name the organic product and state one possible use of this product.

(4)
(Total 12 marks)
53. An organic compound X reacts with excess acidified potassium dichromate(VI) to form compound Y, which reacts
with sodium carbonate to produce CO2(g).

What is a possible formula for compound X?

A. CH3CH2COOH C. CH3CH(OH)CH3

B. CH3CH2CH2OH D. (CH3)3COH

(Total 1 mark)
54. Ethene is an unsaturated hydrocarbon used as a starting material for many organic chemicals.

(a) State the meaning of the term unsaturated hydrocarbon.

(1)
 (b) State an equation for the conversion of ethene to ethanol and identify the type of reaction.

(2)
(c) Describe the complete oxidation of ethanol. Include the conditions, reagents required and any colour
changes. Name the organic product X.

(4)
(d) State an equation for the reaction between ethanol and compound X. Include any other reagent required.
Name the organic compound Z and state one use of this product.

(4)
(Total 11 marks)
55. The equation for a reaction of ethane is

CH3CH3 + Cl2 ® CH3CH2Cl + HCl

The mechanism of this reaction involves initiation, propagation and termination steps. Describe this reaction,
including equations for each step and the role of ultraviolet light.

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(Total 5 marks)
56. Which formula represents an aldehyde?

A. CH3CH2CHO C. CH3CH2COOH

B. CH3COCH3 D. CH3COOCH3

(Total 1 mark)

57. The following transition state is formed during the reaction of a halogenoalkane with aqueous sodium hydroxide:

H 3C C H 3

H O C Br

(a) Deduce the structure of the halogenoalkane. Classify it as primary, secondary or tertiary, giving a reason for
your choice.

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(2)
(b) The mechanism of this reaction is described as SN2. Explain what is meant by the symbols in SN2. Predict a
rate expression for this reaction.

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(3)
(c) The same halogenoalkane reacts with sodium hydroxide by an S N1 mechanism. Deduce the structure of the
intermediate formed in this reaction.

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(1)
 (Total 6 marks)
58. (i) Draw the structural formula of propan-2-ol.

(1)
(ii) Identify the alcohol as primary, secondary, or tertiary.

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(1)
(iii) Identify the organic product formed by the oxidation of this alcohol using acidified potassium
dichromate(VI) solution.

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(1)
(Total 3 marks)
59. Secondary halogenoalkanes can undergo nucleophilic substitution reactions by both S N1 and SN2 mechanisms. The
mechanism showing the formation of the transition state in the reaction between 2-bromobutane and potassium
hydroxide can be represented as follows.

C H 2C H 3
H C H 2C H 3

H C Br H O C B r

CH 3 :O H – CH

(a) Identify the type of mechanism shown.

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(1)
(b) State and explain how the following changes would alter the rate of the reaction by this mechanism.

(i) using water instead of potassium hydroxide.

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(2)
(ii) using bromoethane instead of 2-bromobuture.

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(2)
(Total 5 marks)
60. Which statement about successive members of all homologous series is correct?

A. They have the same empirical formula.

B. They differ by a CH2 group.

C. They have the same physical properties.

D. They differ in their degree of unsaturation.

(Total 1 mark)
61. The following is a three-dimensional representation of an organic molecule.
 Which statement is correct?

A. The correct IUPAC name of the molecule is 2-methylpentane.

B. All the bond angles will be approximately 90°.

C. One isomer of this molecule is pentane.

D. The boiling point of this compound would be higher than that of pentane.

(Total 1 mark)
62. Which compound forms when hydrogen bromide is added to but-2-ene?

A. 2-bromobutane C. 1-bromobutane

B. 2,3-dibromobutane D. 1,2-dibromobutane

(Total 1 mark)
63. 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 C. II and III only

B. I and III only D. I, II and III

(Total 1 mark)
64. Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products are most likely to be
formed during this reaction?

A. Carbon monoxide and water

B. Carbon monoxide and hydrogen

C. Carbon dioxide and hydrogen

D. Carbon dioxide and water

(Total 1 mark)
65. (a) List two characteristics of a homologous series.

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(1)
(b) Ethanol and ethanoic acid can be distinguished by their melting points. State and explain which of the two
compounds will have a higher melting point.

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(2)
(c) Draw the three isomers containing the alcohol functional group of formula C4H9OH.

(2)
(Total 5 marks)
66. 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.

(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)
67. (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)
68. (i) Identify the formulas of the organic products, A–E, formed in the reactions, I–IV:
 
H H
I. CH3(CH2)8OH + K2Cr2O7 ® A ®
 B

II. (CH3)3CBr + NaOH 

® C


H
III. (CH3)2CHOH + K2Cr2O7 
® D

IV. H2C=CH2 + Br2 

® E

(5)
(ii) H2C=CH2 can react to form a polymer. Name this type of polymer and draw the structural formula of a
section of this polymer consisting of three repeating units.

(2)
(Total 7 marks)
MARKSCHEME
1. A[1] 2. D[1] 3. C[1]
4. (i) butane;
13
C4H10(g) + 2 O2(g) ® 4CO2(g) + 5H2O(l);
(ignore state symbols, accept balancing using 13O2 )
[1] for all formulas and [1] for balancing equation.
CO produced;
CO is poisonous/combines with hemoglobin/OWTTE;
or
C;
which causes respiratory problems; 5
(ii) add Br2 (water);
valid test needed to score further marks.
A – no effect;
B – would decolorise Br2 (do not accept discolour); 3
(iii) CH3CH==CHCH3 + HBr ® CH3CHBrCH2CH3; 3
[1] for HBr in balanced equation, [1] for structure of product.
addition;
[11]
5. D[1]
6. (a) change/replacement of atom/group (in molecule);
by species with a non-bonding/lone pair of electrons/attracted to electron
deficient part of molecule (OWTTE)/Lewis base; 2
(b) (i)
C H 3 C H 2 C H 2 C H 2B r / C H 2 C H C H 2B r
CH 3 1
(ii) CH3–––CH2–––CHBr–––CH3 1
(iii)
CH 3

CH 3 C Br
CH 3 1
Position of Br must be clearly shown
In (i), (ii) and (iii), all C—C bonds must be shown. Do not penalize missing
H atoms.
[5]
7. C[1] 8. D[1]
9. (i) II reacts with Br2
II is an alkene/has unsaturated R group/C C present, I contains
 only saturated R groups; 2
(ii) addition polymerization;
( CH CH 2 ) ( CH CH 2 )
O O

C CH O
O
H
accept 2
[4]
10. (i) C4H10 : non-polar, only van der Waals’ forces that cannot replace/
interact with H–bonding in water;
C2H5Cl : only slightly polar/not capable of H–bonding with water; 2
(ii) (CH3)2CO: highly polar/forms H–bonding with water;
C3H7OH : forms H–bonding with water (as H is bonded to O); 2
[4]
11. B[1] 12. B[1]
13. (a) ethene; 2
H H
C C / CH 2 C H 2

H H
(b) A addition/hydration;
H2O/water/steam;
B oxidation;
acidified K2Cr2O7
Accept acidified KMnO4. 4
(c)
H H
C C / CH 2 CH Cl

H Cl

Cl H
H C C C l / C H 2 C lC H 2 C l
H H ;
The compound formed directly may be circled or indicated by some 3
other means. Accept any other structure showing a Cl atom on each C atom.
(d)
H C l
H C C C l / C H 3 C H C l2
H H ;
addition across a double bond occurs at both C atoms/OWTTE; 2
If 1,1-dichloroethane is given in (c) accept 1,2-dichloroethane as the isomer as
ECF but Award [1] max;
(e) addition polymer; 2
H H H H H H
C C C C C C / ( C H 2 C H 2 )3 ;
H H H H H H a llo w ( CH2 ) 3
(f) condensation polymer;
polyesters;
polyamides; 3
[16]
14. A[1] 15. B[1] 16. B[1] 17. D[1]
 H H

C C

18. (i) CH2CHCl/CH2 = CHCl/ H C l; 1

(ii) addition (polymerization);
(carbon-carbon) double bond/unsaturation/OWTTE; 2
H H
C C
(iii) H C l ; 1
(iv) monomers have smaller molecules/surface area than polymers;
with weaker intermolecular/Van der Waals’ forces; 2
Accept opposite argument for polymers.
[6]
19. A[1] 21. C[1] 23. B[1]
20. B[1] 22. D[1] 24. A[1]
25. (a) 1
H

C Cl

H
(b) Cl2 → 2Cl• initiation;
Cl• + C6H5CH3 → C6H5CH2• + HCl propagation;
C6H5CH2• + Cl2 → C6H5CH2Cl + Cl• propagation;
any correct termination equation termination 5
Award [1] for each correct equation.
Award [1] for correct naming throughout.
Ignore “curly arrows”.
(c) breaks Cl—Cl bond homolytically/produce free radicals; 1
[7]
26. B[1] 27. D[1]
28. (a) same general formula/CnH2n;
formulas of successive members differ by CH2;
similar chemical properties/same functional group;
gradation/gradual change in physical properties; 3
Award [1] each for any three.
(b) but-2-ene;
Accept 2-butene.
strongest intermolecular/van der Waals’ forces;
largest (molecular) mass/size/surface area/area of contact; 3
(c) CH2CHCH2CH2CH3/CH3CHCHCH2CH3/any correct branched structure;
Accept more detailed formula.
pent-1-ene/pent-2-ene; 2
Name must match formula.
Accept 1-pentene/2-pentene.
(d) C4H8 + HBr ® CH3CH2CHBrCH3;
Award [1] for all molecular formulas correct and [1] for correct product structure.
Award [1] for completely correct equation starting with
but-1-ene.
addition; 3
(e) oxidation/redox;
2
(potassium) dichromate(VI)/ Cr2 O 7 ;
(sulfuric) acid;
distilling off propanal as it is formed;
heating under reflux (to obtain propanoic acid); 5
(f) (propan-1-ol) hydrogen bonding;
(propanal) dipole-dipole attractions;
(propanoic acid) hydrogen bonding;
propanoic acid > propan-1-ol > propanal; 4
[20]
+ 
29. (CH3)3CI ® (CH3)3C + I ;
 + 
(CH3)C + OH ® (CH3)3COH; 2
Do not allow SN 2 reaction.
[2]
30. D[1] 31. C[1] 32. A[1] 33. D[1]
34. (a) replacement of atom/group (in a molecule)/OWTTE;
Do not accept substitution.
by a species with a lone pair of electrons/species attracted to an
electron-deficient carbon atom; 2
(b) correct structure of (CH3)3CBr;
curly arrow showing CBr bond fission;
+
correct structure of (CH3)3C ;

curly arrow showing attack by OH on correct C atom;
correct structure of (CH3)3COH; 4
Award [1] each for any four.
(c) correct structure of CH3CH2CH2CH2Br;
curly arrow showing CBr bond fission;
correct structure of transition state showing charge and all bonds;

curly arrow showing attack by OH on correct C atom;
correct structure of CH3CH2CH2CH2OH; 4
Award [1] each for any four.
(d) secondary
CH3CHBrCH2CH3;
2-bromobutane;
other primary
(CH3)2CHCH2Br;
1-bromo-2-methylpropane; 4
14]
35. D[1] 36. A1] 37. A[1]
38. (a) same general formula;
successive members differ by CH2;
Do not allow elements or just “they”.
similar chemical properties;
Allow same/constant.
gradual change in physical properties;
Do not allow change periodically.
same functional group; 2
Award [1] each for any two.
(b) add bromine (water);
alkanes  no change/stays or turns brown;
Allow red-brown or any combination of brown, orange or yellow.
alkenes  bromine (water) decolorizes;
Do not allow clear or discoloured.
or
add (acidified) KMnO4;
alkanes  no change;
alkenes  KMnO4 decolorizes/brown/black; 3
[5]
39. (i) (SN2 mechanism) 3
Cl

CH 2 CH 2 CH 2 CH 3 ;

–
H O
c u r ly a r ro w m u s t s ta r t fro m O o r n e g a tiv e c h a rg e

Cl

H O CH 2 CH CH 2 CH 3 ;
2
 Intermediate structure showing overall negative charge and partial bonds.
Accept negative charge to be indicated as delocalised between the HO-CH 2-Cl.

® HO  CH2CH2CH2CH3 + Cl ;
(ii) (SN1 mechanism) 2
CH 3 CH 3

CH 3 C Cl CH 3 C + C l- ;

CH 3 CH 3
-
fo r m a tio n o f c a r b o c a tio n / lo s s o f C l

CH 3 CH 3

CH 3 C + O H - CH 3 C O H ;

CH 3 CH 3

-
c a r b o c a tio n + O H
[5]
40. C[1]
41. butan-1-ol: butanal;
butanoic acid;
butan-2-ol: butanone;
2 methylpropan-2-ol: no oxidation;
Also accept correct structures. Where both name and structure given structure
must be correct and name largely correct.
[4]
42. (a) UV light/sunlight (present); 1
(b) Throughout accept radical with or without •
initiation reaction(s):
Cl2 ® 2Cl•; 1
propagation reactions:
Cl• + CH3CH3 ® CH3CH2• + HCl;
CH3CH2• + Cl2 ® CH3CH2Cl + Cl•; 2
termination reactions:
CH3CH2• + Cl• ® CH3CH2Cl;
2Cl• ® Cl2;
2CH3CH2• ® CH3CH2CH2CH3; 1
Award [1] for any termination reaction.
If initiation, propagation, termination not labelled or incorrectly labelled award
[3] max.
[5]
43. A[1]
44.
H H H

H C C C C H ;

H H O H
h ig h e r;
[2]
45
. C[1] 46. A[1] 47. D[1] 48. B[1]
49. (i) C4H8 + Br2 ® C4H8Br2;
Equation scores [1].
CH3CHBrCHBrCH3; 2
 Accept more detailed formula.
(ii) addition; 1
[3]
50. propan-2-ol;
Accept 2-propanol.
oxidation/redox;
(potassium/sodium) dichromate(VI)/potassium manganate(VII);
 2
Accept just dichromate, permanganate, KMnO4 , Mn O4 , K2Cr2O7, Cr2 O7 .
(sulfuric) acid;
heat under reflux;
[5]
51. (i)
C H 2CH 3

H O C B r

H CH 3

all five groups around C correct;

negative charge and dotted lines to OH and Br correct; 2
nd
Do not award 2 mark if bond from OH (i.e. OH-----).
+ 
(ii) CH3CH2CH(CH3)Br ® CH3CH2CH(CH3) + Br ;
+ 
CH3CH2CH(CH3) + OH ® CH3CH2CH(CH3)OH; 2
Accept C4H9 instead of CH3CH2CH(CH3) throughout.
[4]
52. (a)
H H

C C ;

H H
Allow CH2=CH2.
a hydrocarbon that contains at least one C=C (or CºC)/carbon-carbon
double bond (or triple bond)/carbon to carbon multiple bond; 2
Do not accept just “double bond”.
(b) C2H4 + H2O ® C2H5OH;
addition/hydration reaction; 2
(c) heat under reflux;
EITHER
2– +
potassium dichromate(VI)/K2Cr2O7/Cr2O7 and acidified/H ;
orange to green;
OR
–
potassium permanganate/manganate(VII)/KMnO4/MnO4 and
+;
acidified/H
purple to colourless;
Penalize wrong oxidation state, but not missing oxidation state.
ethanoic acid; 4
(d) CH3COOH + C2H5OH ® CH3COOCH2CH3 + H2O;
Accept CH3COOC2H5
sulfuric acid/H2SO4/(ortho)phosphoric acid/H3PO4;
ethyl ethanoate;
solvent/flavouring/perfumes/plasticizers;. 4
[12]
53. B[1]
54. (a) a hydrocarbon that contains at least one C=C (or CºC)/carbon-carbon
double bond (or triple bond)/carbon to carbon multiple bond; 1
Do not accept just “double bond”.
(b) C2H4 + H2O ® C2H5OH;
addition/hydration reaction; 2
(c) heat under reflux;
 EITHER
2– +
potassium dichromate(VI)/K2Cr2O7 / Cr2O7 and acidified/H ;
orange to green;
OR
– +
potassium permanganate/manganate(VII)/KMnO4 / MnO4 and acidified/H ;
purple to colourless;
Penalize wrong oxidation state, but not missing oxidation state.
ethanoic acid; 4
(d) CH3COOH + C2H5OH CH3COOCH2CH3 + H2O;
+
accept equations including H .
Reversible arrow not required for the mark.
sulfuric acid/H2SO4/(ortho)phosphoric acid/H3PO4;
Z – ethyl ethanoate;
solvent/flavouring/perfumes/plasticizers; 4
[11]
55. ultraviolet light causes ClCl bond to split;
Cl2 ® 2Cl•;
Cl• + CH3CH3 ® CH3CH2• + HCl;
CH3CH2• + Cl2 ® CH3CH2Cl + Cl•
CH3CH2• + Cl• ® CH3CH2Cl/other correct termination step; 5
Penalize missing · symbol once only.
If different alkane used, then deduct [1].
No penalty for not labelling steps, but deduct [1] if any wrongly labelled.
[5]
56. A[1]
57. (a) (CH3)2CHBr/more detailed formula;
secondary/2° because two alkyl groups attached to C with Br; 2
(b) nucleophilic substitution;
bimolecular/molecularity of two/two species in rate-determining step;
Accept second order.

rate = k [(CH3)2CHBr][OH ]; 3
No penalty for incorrect halogenoalkane formula.
+
(c) (CH3)2CH /more detailed formula; 1
[6]
58. (i)
H

CH 3 C CH 3 / C H 3 C H (O H )C H 3 ;

O H
1
Allow bond to HO rather than OH or halfway between the two
(ii) secondary; 1
(iii) CH3COCH3/propanone/acetone; 1
Allow ECF from a different alcohol drawn in (i)
[3]
59. (a) SN2 / bimolecular; 1
(b) (i) reaction slower;
neutral/uncharged/less polar/electrons donated less easily in H 2O; 2
(ii) reaction faster;
less bulky group/reduced steric hindrance; 2
[5]
60. B[1] 62. A[1] 64. A[1]
61. C[1] 63. B[1]
65. (a) one general formula/same general formula;
differ by CH2;
similar chemical properties;
gradual change in physical properties; 1
Award [1] for any two of the above characteristics.
(b) ethanol lower/ethanoic acid higher;
due to larger mass of ethanoic acid/stronger van der Waals’/
 London/dispersion forces;
due to stronger hydrogen bonding/2 hydrogen bonds per molecule; 2
Accept either answer for second mark.
(c)

2
Allow condensed structural formulas such as CH3CH2CH2CH2OH.
Award [2] for all three correct isomers, [1] for any two correct isomers.
[5]
66. (i) (Empirical formula =) C8H8O3;
H
H O O
H C C H
H O
;

H H
H 2
Allow double bonds on arene in alternate positions, or allow delocalized
representation (of pi electrons).
(ii) the bond at 0.1373 nm is a double bond and the bond at 0.1424 nm is a
single bond;
in CO2(g) both bonds are double bonds and would have a value
around 0.137 nm; 2
(iii) Ester;
Arene/benzene ring;
Alcohol; 2
Award 2 for any three correct, award [1] for any two correct.
Do not accept alkane as a type of functional group in this molecule.
[6]
67. (i) boiling point increases as the number of carbons increases/OWTTE;
Greater Mr and hence greater van der Waals’/London/dispersion forces present; 2
hv / UV light
(ii) CH4 + Cl2  ® CH3Cl + HCl;
Do not award mark if hv/uv light is not given.
Initiation step:
hv / UV light
Cl2  ® 2Cl•;
Do not award mark if hv/uv light is not given.
Penalize once only.
Propagation step:
CH4 + Cl• → CH3• + HCl;
CH3• + Cl2 → CH3Cl + Cl•;
Termination step:
Cl• + Cl• ® Cl2 or Cl• + CH3• ® CH3Cl or CH3• + CH3• → CH3CH3; 5
Allow fish-hook half-arrow representations i.e. use of .
Penalize use of full curly arrows once only.
Penalize missing dots on radicals once only.
[7]
68. (i) A. = CH3(CH2)7CHO;
B. = CH3(CH2)7COOH/CH3(CH2)7CO2H;
C. = (CH3)3COH;
D. = (CH3)2CO;
E. = BrCH2CH2Br; 5
Allow correct structural formulas.
(ii) addition;
/-(CH2-CH2)3-/-(CH2)6-; 2
[7]