Alcohols and Haloalkanes

Answer all the questions.
1. Bromoethane can be prepared by heating ethanol with NaBr.
What are the conditions for this reaction?
A Acid catalyst
B Ultraviolet radiation
C Halogen carrier
D Nickel catalyst
Your answer
[1]
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2. Butan-1-ol is reacted with acidified potassium dichromate(VI) using the apparatus shown below.
What is the organic product of this reaction?
A But-1-ene
B Butanone
C Butanal
D Butanoic acid
Your answer
[1]

3. When heated with NaOH(aq), 1‐iodobutane is hydrolysed at a much faster rate than 1‐chlorobutane.
Which statement explains the different rates?
A The C−I bond enthalpy is greater than the C−Cl bond enthalpy.
B The C−I bond is less polar than the C−Cl bond.
C The C−I bond has a C atom with a greater δ+ charge than in the C−Cl bond.
D The C−I bond requires less energy to break than the C−Cl bond.
Your answer
[1]

4. Which alcohol can be oxidised by K2Cr2O7 and H2SO4 to form a ketone?
Your answer
[1]
5. Which alcohol will not react with potassium dichromate(VI) in sulfuric acid?
A CH3CH2CH(OH)CH2CH3
B CH3CH2CH(CH3)CH2OH
C (CH3)2CHCH(CH3)OH
D (CH3CH2)2C(CH3)OH
Your answer
[1]

6. The compound shown below reacts with a mixture of NaBr and H2SO4.
What is the relative molecular mass of the organic product?
A 138.9
B 155.9
C 201.8
D 235.8
Your answer
[1]

7. A reaction sequence is shown below:
Step 1 CH3CH=CHCH3 + HBr → CH3CH2CHBrCH3

Step 2 CH3CH2CHBrCH3 + NaOH → CH3CH2CH(OH)CH3 + NaBr
Which type of reaction mechanism is involved in each step?
Step 1 Step 2
A electrophilic addition electrophilic substitution
B electrophilic addition nucleophilic substitution
C nucleophilic addition electrophilic substitution
D nucleophilic addition nucleophilic substitution
Your answer
[1]

8. A chemist investigates the rate of hydrolysis of the haloalkanes.
Which of the following statements is / are true?
1: A fluoroalkane gives the slowest rate of hydrolysis.
2: The rate of reaction depends on the strength of the carbon–halogen bond.
3: The rate of reaction depends on the polarity of the carbon–halogen bond.
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
9. Which volume of oxygen gas, at room temperature and pressure, is required for complete combustion of 1.25 ×
10–3 mol of propan-1-ol?
A 105 cm3
B 120 cm3
C 135 cm3
D 120 cm3
Your answer
[1]

10. Which molecule is the most soluble in water?
Your answer
[1]
11. This question is about the properties and reactions of butan-2-ol.
Some properties of butan-2-ol are listed in the table.
Melting point –115 °C

Boiling point 99.5 °C
Why is butan-2-ol classified as a secondary alcohol?
[1]

12. Haloalkanes can undergo hydrolysis.
A student carries out an experiment to find the relative rate of hydrolysis of 1-chloropropane, C3H7Cl,
1-bromopropane, C3H7Br, and 1-iodopropane, C3H7I.
The student adds 2 cm3 of ethanol to 2 cm3 of aqueous silver nitrate to three test tubes labelled A, B and C.
The student adds 5 drops of a different haloalkane to each test-tube in rapid succession and shakes each tube.
The student measures the time for a precipitate to form in each test-tube.
The results are shown below.
Test tube Haloalkane Time taken for reaction

to take place
A C3H7Cl about half an hour
B C3H7Br a few minutes
C C3H7I a few seconds
(i) Write an ionic equation involving aqueous silver nitrate for formation of one of the precipitates.
[1]
(ii) What do the experimental results tell you about the carbon–halogen bond enthalpies?
[1]
(iii) How could the student modify their experiment so that it could be completed in less time?
[1]
13. Give chemical explanations for the following statements.
The rate of hydrolysis of 1-bromobutane is faster than that of 1-chlorobutane.
[1]

14. Compound A is an alkene.
Compound A can be made from alcohol B by heating with an acid catalyst.
Suggest two possible structures for alcohol B .
[2]

15. Compound B, shown below, can be used to synthesise organic compounds with different functional groups.
Some reactions involving compound B are shown in the flowchart below.
Complete the flowchart, showing the structures of organic compounds C and D.
[2]

16. This question is about the properties and reactions of butan-2-ol.
Some properties of butan-2-ol are listed in the table.
Melting point –115 °C

Boiling point 99.5 °C
Butan-2-ol can be oxidised by heating with an oxidising agent.
(i) Write an equation for the reaction.
Use [O] to represent the oxidising agent and show the structure of the organic product.
[2]
(ii) A student plans to carry out this oxidation using the apparatus shown in the diagram.

Give one reason why the apparatus is not suitable and describe a more suitable way of carrying out this
oxidation.
[2]

17. Alcohols are used in organic synthesis.
Pentan-2-ol can be prepared by the alkaline hydrolysis of 2-iodopentane.
CH3CH(I)CH2CH2CH3 + NaOH → CH3CH(OH)CH2CH2CH3 + NaI
The reaction mixture is boiled for 20 minutes.
(i) State the most appropriate technique that could be used to boil the reaction mixture for 20 minutes.
[1]
(ii) Describe the mechanism for the alkaline hydrolysis of 2-iodopentane.
In your answer, include the name of the mechanism, curly arrows and relevant dipoles.
name of mechanism: _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
[4]

18. This question is about alkenes.
When alcohol A is heated with an acid catalyst, a reaction takes place forming alkene B.
The equation for this reaction is shown below as Equation 16.1.
CH3CH(CH3)CH2CHOHCH3 → CH3CH(CH3)CHCHCH3 + H2O Equation 16.1

alcohol A alkene B
(i) State the type of reaction in Equation 16.1.
[1]
(ii) Alkene B has two stereoisomers.
Explain what is meant by the term stereoisomers, and draw the skeletal formulae of the two stereoisomers
of alkene B.
[3]
(iii) The reaction of A with an acid catalyst also forms another alkene, C.
Alkene C is a structural isomer of alkene B.
Suggest the structure of alkene C.
[1]
(iv) * A student carries out the reaction in Equation 16.1 using 9.26 g of alcohol A.

The student obtains a liquid reaction mixture containing a mixture of organic products and the acid catalyst.
The student purifies the reaction mixture to obtain the liquid alkene B with a percentage yield of 75.0%.
Describe a method to obtain a pure, dry sample of alkene B from the reaction mixture and calculate the mass
of alkene B that the student produced.
[6]

19. Alcohols can be converted into haloalkanes in a substitution reaction.
Plan an experiment to prepare approximately 0.1 mol of 2-bromopentane,

CH3CHBrCH2CH2CH3, from pentan-2-ol, CH3CH(OH)CH2CH2CH3.
Your plan should include a calculation of the mass of alcohol required and details of the chemicals to be used in
the reaction.
[2]

20(a). Haloalkanes are hydrolysed by aqueous sodium hydroxide.
(i) Outline the mechanism of the reaction of 1-bromobutane with aqueous sodium hydroxide.
Include curly arrows, relevant dipoles and the structure of the organic product.
[3]
(ii) Name the type of mechanism in (i).
[1]
(iii) The organic product in (i) can be formed faster using a different haloalkane than 1-bromobutane.
Identify this haloalkane.
Explain your answer.
Haloalkane _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
Explanation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
[1]
(b). The use of some haloalkanes, such as chlorotrifluoromethane, has been banned as they form Cl • radicals which
break down ozone.
(i) Construct an equation to show the formation of Cl • radicals from chlorotrifluoromethane.
[1]
(ii) Ozone is broken down by Cl • radicals in a two-step process.

Write the equations for the two steps and the overall equation for this process.
Step 1 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
Step 2 _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
Overall equation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]

(iii) A research chemist found that 1.00 g of Cl • radicals can breakdown 135 kg of O3.
Calculate the number of O3 molecules removed by one Cl • radical.
Give your answer in standard form and to three significant figures.
number of O3 molecules = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]
END OF QUESTION PAPER

Mark Scheme
Question Answer/Indicative content Marks Guidance
1 A 1
Total 1
2 C 1
Total 1
3 D 1 Examiner's Comments
Generally scored well.
Total 1
4 B 1 Examiner's Comments
Total 1
5 D 1
Total 1
6 A 1
Total 1
7 B 1 Examiner's Comments
Total 1
8 B 1
Total 1
9 C 1
Total 1
10 D 1
Total 1

Mark Scheme
11 The –OH group is attached to a carbon 1 ALLOW alcohol / hydroxyl / functional

that is attached to one hydrogen atom group for –OH
OR
The –OH group is attached to a carbon Examiner's Comments
that is attached to two C atoms / alkyl
groups/R groups ✓ The definition of a secondary alcohol was
well known with most candidates being to
express this to gain the mark available.
Total 1
12 i Ag+ + Cl– → AgCl 1

OR
Ag+ + Br– → AgBr
OR
Ag+ + I– → AgI
ii Bond enthalpy decreases C–Cl > C–Br > 1 allow chlorine–carbon bonds are
C–I strongest.
iii Heat the test tubes in a water bath. 1
Total 3
13 The C–Br bond is weaker (than the C–Cl 1 ORA

bond)
Total 1

Mark Scheme
14 2 ALLOW correct structural OR displayed

OR skeletal formulae OR a combination of
above as long as unambiguous
ALLOW any vertical bond to OH,
e.g. ALLOW
DO NOT ALLOW OH–
Examiner's Comments
Many candidates found it difficult to draw

the structures for the two alcohols that
could be dehydrated to produce compound
A. This was surprising as it was a simple
task to add water across the double bond
of compound "A“ resulting in two branched
chained isomers. The most common
incorrect answers were pentan-1-ol and
pentan-2-ol, although some candidates
shortened the chain length resulting in
compounds containing only four carbon
atoms.
Total 2

Mark Scheme
15 Compound C: 2 For structures:

ALLOW correct structural OR skeletal
OR displayed formula OR mixture of the
above
_________________________________
CARE: Tertiary alcohol Connectivity
IGNORE connectivity of bonds to CH3
Compound D: (repeat unit) e.g. ALLOW CH3–
ALLOW any vertical bond to OH,
e.g. ALLOW OH OR OH
||
DO NOT ALLOW OH–

_________________________________
DO NOT ALLOW more than one repeat
unit
REQUIRED: Side links (dotted lines

fine)
NOT Brackets and ‘n’
REQUIRED:
Examiner's Comments
This part was answered well. If a mark was

lost, it was almost always due to
compound C, especially at the low scoring
end of the range. Many struggled with the
structure of a tertiary alcohol or omitted H
atoms from the structure.
Compound D was generally drawn

correctly by candidates of all abilities. If the
mark was not credited, it was usually due
to not removing the double bond, or
drawing more than one repeat unit.
Total 2

Mark Scheme
16 i Equation 2 ALLOW molecular formulae: C4H10O and

CH3CH(OH)CH2CH3 + [O] → C4H8O
CH3COCH2CH3 + H2O ✓ ALLOW C4H9OH
ALLOW C2H5 for CH3CH2
Structure of product could be allowed
from equation ALLOW correct structural OR displayed
OR skeletal formulae OR a combination of
CH3COCH2CH3 ✓ above as long as unambiguous
Examiner's Comments
The majority of candidates were able to

identify the structure of the ketone formed
in the oxidation of butan-2-ol but many
were not able to construct a suitable
equation. Water was often omitted from the
equation on the right hand side whilst
sometimes the equation was incorrectly
balanced with a 2 being placed in front of
the [O]. The most able candidates normally
scored both marks.
ii Butan-2-ol/butanone is flammable IGNORE vague answers about health and

OR safety
Butan-2-ol / butanone is volatile / low ALLOW alcohol for butan-2-ol
boiling point ALLOW ketone for butanone
OR
ii Butan-2-ol / butanone will evaporate / boil 1 DO NOT ALLOW the product or reactant.
away ✓ DO NOT ALLOW distillation
ii (Heat under) reflux OR a description of 1 DO NOT ALLOW any reference to closed

reflux with vertical condenser and a round system.
bottomed or pear shaped flask with source
of heat. ✓ Examiner's Comments
Another question requiring candidates to

evaluate a practical activity where
responses were on the whole
disappointing. Very few candidates were
able to access both of the marks with the
harder of the two marks being for
suggesting why the apparatus was not
suitable for the experiment. Clearly many
candidates were able to suggest a better
method of carrying out the experiment with
reflux being often quoted.
Total 4

Mark Scheme
17 i Reflux 1
ii Nucleophilic substitution (1) 4
Mechanism
Curly arrow from lone pair on OH– to δ+ The curly arrow must start from the oxygen
carbon atom (1) atom of the OH– and must start from either
the lone pair or the negative charge
Curly arrow and dipole on C–I bond (1)
Correct products (1)
do not allow attack by NaOH
Total 5

Mark Scheme
18 i Elimination 1 ALLOW Dehydration
ii Same structural formula 3 ALLOW have the same structure /

AND displayed formula / skeletal formula
Different arrangement (of atoms) in space
OR different spatial arrangement DO NOT ALLOW same empirical formula
OR same general formula
Stereoisomers have the same formula or

molecular formula is not sufficient
Reference to E/Z isomerism or optical

isomerism is not sufficient
IGNORE names
IF skeletal formula is not used ALLOW one

mark if both stereoisomers of alkene B are
shown clearly.
iii 1 ALLOW correct structural OR skeletal OR

displayed formula OR mixture of the above
IGNORE names

Mark Scheme
iv * Please refer to the marking instruction 6 Indicative scientific points, with bulleted
point 10 for guidance on how to mark this elements, may include:
question.
1. Purification
Level 3 (5–6 marks)
Outlines full details of how a pure sample Use of a separating funnel to
of B is obtained from the reaction mixture. separate organic and aqueous layers
AND Drying with an anhydrous salt, e.g.
Correctly calculates mass of B MgSO4, CaCl2, etc.
Redistillation
Purification steps are clear, in the
correct order, using appropriate Incorrect purification method is NOT
scientific terms. worthy of credit.
Calculation shows all relevant steps
and mass given to 3 significant figures. 2. Mass of B obtained

Some details of how a sample of B is
obtained from the reaction mixture.
AND = theoretical n(B)
Attempts a calculation which is mostly Actual n(B) obtained
correct.
Purification steps lack detail, e.g. no mass B = 84 × 0.0681 = 5.72 g

drying agent or no explanation of
separation, or only some scientific CHECK for extent of errors by ECF
terms used.
Calculation can be followed but Alternative correct calculation may
unclear. calculate the mass of B as 0.0908 × 84 =

Few or imprecise details of how a sample
of B is obtained from the reaction mixture.
AND Calculation must attempt to calculate n(A)
Attempts to calculate the mass of B using in mol.
mole approach but makes little progress Simply finding 75% of the initial mass of
with only 1 step correct. alcohol A, 9.26, is NOT worthy of credit.
Purification step is unclear with few

scientific terms and little detail, e.g. just
‘separate the layers and dry’.
Calculation is difficult to follow and
lacking clarity
0 marks
No response or no response worthy of
credit.
Total 11

Mark Scheme
19 (Minimum) n(pentan-2-ol) required = 0.1 × 2

88 = 8.8 g (1)
React the alcohol with a mixture of NaBr allow HBr

AND H2SO4 AND warm (to distil off the
product) (1)
Total 2

Mark Scheme
20 a i 3 ANNOTATE ANSWER WITH TICKS AND

CROSSES
Curly arrow must come from lone pair on O

curly arrow from HO– to carbon atom of C - of HO– OR OH–
Br bond ✓ OR from minus on O of HO– ion (no need
to show lone pair if curly arrow came from
Dipole shown on C–Br bond, Cδ+ and Brδ–, negative charge)
AND curly arrow from C–Br bond to Br
atom ✓ IGNORE alkyl group in the first marking
point
_______________________________
ALLOW SN1 mechanism
First mark
Dipole shown on C–Br bond, Cδ+ and Brδ–,
AND curly arrow from C - Br bond to Br
atom ✓
_______________________________ Second mark

Correct carbocation AND curly arrow from
HO– to carbocation
correct organic product AND Br– ✓
Curly arrow must come from lone pair on O

of HO–
OR
OH–
OR from minus on O of HO– ion (no need
to show lone pair if curly arrow came from
negative charge) ✓
Third mark
correct organic product AND Br– ✓
____________________________
ii Nucleophilic substitution ✓ 1

Mark Scheme
iii 1 Note: the haloalkane could be identified by

1-iodobutane a correct structure e.g. CH3CH2CH2CH2I
AND IGNORE molecular formula

IGNORE iodobutane (no locant number)
C–I bonds are weaker (than C-Br) Statement must be comparative

OR C–I bond has a lower bond enthalpy ALLOW ORA
OR C–I bond needs less energy to break IGNORE C–I bond is longer
OR C–I bond is easier to break ✓ IGNORE polarity and references to
electronegativity
b i CF3Cl → CF3• + Cl•✓ 1 Note: dots are required
ii Step 1: Cl• + O3 → Cl O• + O2 ✓ 3 ALLOW one mark for both correct symbol

equations in propagation steps with (any or
Step 2: ClO• + O → Cl• + O2 ✓ all) dots missing or extra dots.
e.g. Cl• + O3• → ClO + O2
ClO• + O• → Cl + O2•
Overall equation: O3 + O → 2O2✓
iii FIRST CHECK THE ANSWER ON THE 3 If there is an alternative answer, check
ANSWER LINE to see if there is any ECF credit
IF answer = 9.98 × 104 award 3 marks possible
ALLOW 0.0282 up to calculator value of

n(Cl•) = = 0.02817 (mol)✓
0.02816901408 correctly rounded to 3 or
more sig. fig.
ALLOW 3SF: 2810 up to calculator value

n(O3) = = 2812.5 (mol) ✓ of 2812.5 correctly rounded
n(Cl•) : n(O3) = = 9.98 × 104 ✓

Note: use of 0.0282 mol Cl• gives 9.97 ×
Must be in standard form AND to 3SF
104
Total 12
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Alcohols and Haloalkanes

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Answer all the questions.

1. Bromoethane can be prepared by heating ethanol with NaBr.

What are the conditions for this reaction?

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What is the organic product of this reaction?

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Which statement explains the different rates?

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What is the relative molecular mass of the organic product?

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Step 1 CH3CH=CHCH3 + HBr → CH3CH2CHBrCH3

Which type of reaction mechanism is involved in each step?

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1: A fluoroalkane gives the slowest rate of hydrolysis.

2: The rate of reaction depends on the strength of the carbon–halogen bond.

3: The rate of reaction depends on the polarity of the carbon–halogen bond.

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Some properties of butan-2-ol are listed in the table.

Melting point –115 °C

Why is butan-2-ol classified as a secondary alcohol?

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The results are shown below.

Test tube Haloalkane Time taken for reaction

13. Give chemical explanations for the following statements.

The rate of hydrolysis of 1-bromobutane is faster than that of 1-chlorobutane.

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Compound A can be made from alcohol B by heating with an acid catalyst.

Suggest two possible structures for alcohol B .

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Some reactions involving compound B are shown in the flowchart below.

Complete the flowchart, showing the structures of organic compounds C and D.

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Some properties of butan-2-ol are listed in the table.

Melting point –115 °C

Butan-2-ol can be oxidised by heating with an oxidising agent.

(i) Write an equation for the reaction.

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Pentan-2-ol can be prepared by the alkaline hydrolysis of 2-iodopentane.

CH3CH(I)CH2CH2CH3 + NaOH → CH3CH(OH)CH2CH2CH3 + NaI

The reaction mixture is boiled for 20 minutes.

(ii) Describe the mechanism for the alkaline hydrolysis of 2-iodopentane.

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CH3CH(CH3)CH2CHOHCH3 → CH3CH(CH3)CHCHCH3 + H2O Equation 16.1

(i) State the type of reaction in Equation 16.1.

(ii) Alkene B has two stereoisomers.

Alkene C is a structural isomer of alkene B.

Suggest the structure of alkene C.

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Plan an experiment to prepare approximately 0.1 mol of 2-bromopentane,

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(ii) Name the type of mechanism in (i).

Identify this haloalkane.

Explain your answer.

(i) Construct an equation to show the formation of Cl • radicals from chlorotrifluoromethane.

(ii) Ozone is broken down by Cl • radicals in a two-step process.

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Overall equation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]

Calculate the number of O3 molecules removed by one Cl • radical.

Give your answer in standard form and to three significant figures.

number of O3 molecules = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [3]