Edexcel A-Level Chemistry AS Paper 2, June 2024: Question 5
12 marks · Medium difficulty · Practical Techniques and Data Analysis
Explain the experimental procedure for preparing and purifying 1-bromobutane from butan-1-ol, including safety precautions, side-reaction prevention, apparatus setup for distillation, and separation of immiscible layers.
Practise this questionQuestion
Question text
5 The apparatus shown can be used for the conversion of butan‑1‑ol
to 1‑bromobutane.
tap funnel
concentrated sulfuric acid
still head
water out
water in
ice‑water bath
butan‑1‑ol,
sodium bromide, water
Procedure
Step 1 In a fume cupboard, 10 g of sodium bromide, 10 cm3 of deionised water and
7.5 cm3 of butan‑1‑ol are placed in a pear‑shaped flask containing some
anti‑bumping granules in the apparatus shown.
Step 2 10 cm3 of concentrated sulfuric acid is dripped slowly from a tap funnel into
the reaction mixture in the pear‑shaped flask.
Step 3 The tap funnel and still head are removed from the top of the condenser.
The flask and condenser are taken out of the ice‑water bath. The flask is
heated for about 45 minutes.
16Step 4 The apparatus is then rearranged for distillation and the distillate of
1‑bromobutane and water is collected in a small beaker, forming two layers.*P76894A01632*
Step 5 The aqueous layer is separated from the 1‑bromobutane layer.
Step 6 The 1‑bromobutane layer is washed with concentrated hydrochloric acid to
remove any unreacted butan‑1‑ol, and then separated.
Step 7 The 1‑bromobutane is then washed with dilute sodium carbonate solution
and then separated.
Step 8 A drying agent is added to the 1‑bromobutane.
Step 9 The 1‑bromobutane is separated from the drying agent.
The 1‑bromobutane is distilled again and collected between 101°C and 103°C.
(a) In Steps 1 and 2 of the procedure, an ice‑water bath and a condenser are used.
The ice helps to prevent side reactions. Redox reactions are one possible
type of reaction which may result in the formation of unwanted organic and
inorganic products.
(i) Give one reason for the presence of the condenser and one reason for the
still head in Steps 1 and 2.
(2)
Condenser
Still head
(ii) Give the name or formula of the oxidising agent responsible for the unwanted
redox reactions.
(1)
(iii) Identify, by name or formula, one of the unwanted inorganic products and
one of the organic products resulting from these*P76894A01732*redoxreactions.
(2)
Inorganic product
Organic product
(iv) Give a reason why ice helps to prevent the formation of these redox products.
(1)
(b) Describe how the apparatus is rearranged for distillation, including the name of
any additional apparatus required.
(3)
(c) The method of separation of the aqueous and organic layers in Step 5 is different
from that used in Steps 6 and 7.
(i) Draw a labelled diagram of the beaker immediately before the separation
in Step 5.
[Density of water = 1.00*P76894A01832*gcm–3
Density of 1‑bromobutane = 1.28 g cm–3]
(1)
(ii) Describe how the aqueous layer can be removed from the beaker in Step 5.
(1)
(iii) Name the piece of apparatus used to separate the organic layer in
Steps 6 and 7.
(1)
(Total for Question 5 = 12 marks)
Mark scheme
Show the mark scheme
Question
Answer Additional Guidance Mark
Number
5(a)(i) An answer that makes reference to the following points: (2)
Either
• the condenser prevents loss of reactants / reagents Allow to prevent loss of (some of the) evapourated /
(to ensure a high yield of product) volatile compounds
/ to return reactants / reagents to the flask so it can Allow condenses gases back into liquids / flask
fully react Allow prevents loss of products
/ to prevent loss of any products formed before Ignore just condenses gas
Step 3
Or
the condenser prevents the escape of flammable / Accept sprays instead of gases
corrosive / poisonous / acidic / toxic / harmful Ignore prevents boiling over
gases Allow named / formula of gases only if they are likely to /
might condense (e.g. bromine)
(1) Do not award toxic HBr / SO2 / CO2 as they will not
condense
Answer must include the hazard so do not award answers
such as bromine might escape
Do not award risk of explosion here
• the still head prevents the build-up of pressure / Award the still head allows any uncondensed gas to
risk of explosion escape
(1) Allow allows for the loss of gas (from the reflux) as it
is open
Question
Answer Additional Guidance Mark
Number
5(a)(ii) An answer that makes reference to the following point: (1)
• (concentrated / conc) sulfuric acid / H SO Ignore H+
Do not award dilute H2SO4
Question
Answer Additional Guidance Mark
Number
5(a)(iii) An answer that makes reference to the following points: (2)
• bromine / Br2 / sulfur dioxide / SO2 (1) Ignore carbon dioxide / CO2
• butanal / butanoic acid / CH3CH2CH2CHO / Allow any type of structural formula, but do not award
CH3CH2CH2COOH (1) molecular formulae
Ignore but-1-ene
For all substances if name and formula are given, both
must be correct
Question
Answer Additional Guidance Mark
Number
5(a)(iv) An answer that makes reference to the following point: (1)
• (lower temperature means) less / fewer collisions have Accept lowers the energy of collisions
sufficient energy (to overcome the activation barrier) Allow no collisions have enough energy (to overcome
the activation barrier)
Allow the reactants do not have enough energy to react
Allow the reactants / reaction / mixture does not have
the activation energy
or Allow not enough energy for the reaction to take place
Allow it prevents the oxidation of bromide ion to
bromine
(lower temperature means) the rate of reaction will Allow the reaction will stop
decrease / the reaction will slow
Question
Answer Additional Guidance Mark
Number
5(b) An answer that makes reference to the following points: Allow three marks may be awarded with a labelled (3)
diagram showing labelled thermometer, condenser and still
head.
thermometer
• (the condenser is removed and) the still head is put
in the pear-shaped flask / a round-bottomed (1)
flask still head
condenser
• a thermometer is added to the top of the still head (1) pear-shaped
(using a quickfit adaptor) flask
• a condenser is added to the still head at the side /
added to the still head diagonally / added to the
still head horizontally / added to the still head at a (1)
downward angle (and a small beaker is placed Allow a stopper / bung in place of a thermometer, but
below the other end of the condenser) must be named
Do not penalise a second collecting vessel (e.g round
bottomed flask) attached to the condenser if there is a way
for pressure to escape
Question
Answer Additional Guidance Mark
Number
5(c)(i) An answer that makes reference to the following point: (1)
• a diagram of a beaker showing an upper aqueous
layer / water and a lower organic layer / water
1-bromobutane
1-bromobutane
Do not award a diagram of a separating funnel
Do not award diagrams of other glassware except beaker /
conical flask
Question
Answer Additional Guidance Mark
Number
5(c)(ii) An answer that makes reference to the following point: (1)
• use a (teat) pipette / syringe to remove the upper Allow use a (teat) pipette / syringe to remove the lower
layer / aqueous layer / water (which is discarded) layer is removed and discard (the remaining) aqueous layer
Allow transfer to a separating funnel and let out the lower
layer
Allow TE on the use of a separating funnel instead of a
beaker in (c)(i) if the layers are correct by opening the tap
to separate the bottom layer
Do not award just use a separating funnel without transfer
Ignore decanting
Allow TE on reversed layers in (c)(i)
Question
Answer Additional Guidance Mark
Number
5(c)(iii) An answer that makes reference to the following point: (1)
• separating funnel / dropping funnel Allow tap funnel
Ignore burette
(Total for Question 5 = 12 marks)
How to answer it
Preparation and Purification of 1-Bromobutane
This 12-mark practical question assesses your understanding of organic synthesis techniques, reaction mechanisms, and laboratory procedures:
- Apparatus functions: Understanding why condensers and still heads are assembled open to air during exothermic additions.
- Redox chemistry of sulfuric acid: Recognising conc. H₂SO₄ as an oxidising agent that reacts with bromide ions and primary alcohols.
- Kinetics: Explaining temperature control using collision theory and activation energy.
- Apparatus conversion: Describing standard simple distillation glassware and its assembly.
- Purification techniques: Liquid-liquid separation, layer identification using densities, and apparatus selection.
Function of Condenser and Still Head
Explaining apparatus roles during addition of concentrated sulfuric acid
✅ Correct Answers
- Condenser: Prevents the loss of volatile reactants/reagents (e.g. butan-1-ol) or products by condensing vapours back into the flask; OR prevents escape of harmful/toxic/flammable vapours. [1 mark]
- Still head: Prevents pressure build-up / prevents risk of explosion by leaving the apparatus open to the atmosphere. [1 mark]
💡 Key Knowledge
The reaction between conc. H₂SO₄ and NaBr/water is vigorously exothermic:
NaBr + H₂SO₄ → HBr + NaHSO₄
Volatile organic liquids (butan-1-ol boiling point = 117 °C, 1-bromobutane = 102 °C) readily vaporise upon heating. The vertical condenser ensures reflux. The side arm of the still head remains unsealed so gas can escape safely.
🧠 Exam Technique
Always state why condensation is useful. Writing just "it condenses gas" is a mere description and scores zero. You must state that it prevents loss of reactants/products.
❌ Common Errors
- Vaguely stating "the still head holds the tap funnel" (this is purely physical support, not its functional chemical/safety purpose).
- Saying the condenser "condenses toxic HBr or SO₂" (these are gases with boiling points well below room temperature and will not condense under cold tap water).
Unwanted Redox Side Reactions
Identifying oxidising agents and redox by-products
✅ Correct Answers
(a)(ii) Oxidising agent: Concentrated sulfuric acid / conc. H₂SO₄ [1 mark]
(a)(iii) Inorganic product: Bromine / Br₂ OR sulfur dioxide / SO₂ [1 mark]
(a)(iii) Organic product: Butanal / CH₃CH₂CH₂CHO OR butanoic acid / CH₃CH₂CH₂COOH [1 mark]
💡 Key Knowledge
Concentrated H₂SO₄ acts as an oxidising agent:
- Oxidation of bromide: 2Br⁻ + H₂SO₄ + 2H⁺ → Br₂ + SO₂ + 2H₂O
- Oxidation of alcohol: Butan-1-ol (primary alcohol) is oxidised to butanal (aldehyde) or butanoic acid (carboxylic acid).
❌ Common Errors
- Writing just "dilute sulfuric acid" for (a)(ii) — dilute acid is NOT an oxidising agent!
- Writing molecular formulae like C₄H₈O for the organic product — structural or displayed formulae are required for organic species to show functional group identity.
- Listing but-1-ene as the redox product — elimination is an acid-catalysed dehydration, NOT a redox reaction.
🧠 Exam Technique
If you give both a name and a formula, both must be correct. If you write "bromine, Br", you lose the mark because the formula of elemental bromine is Br₂.
Role of Ice Bath (Kinetics)
Connecting reaction conditions to collision theory
✅ Correct Answer
At a lower temperature, fewer molecules/collisions have energy greater than or equal to the activation energy (E ≥ Ea), so the rate of these unwanted redox reactions decreases significantly / reaction slows down. [1 mark]
🧠 Exam Technique
You can answer using either:
- Energetics: Lower temperature means fewer particles have the activation energy needed to react.
- Rate: Low temperature dramatically slows down the rate of the unwanted side reaction.
Rearranging Apparatus for Distillation
Converting reflux equipment into simple distillation setup
✅ Correct Description / Points Awarded
- Point 1: The still head is placed directly into the neck of the pear-shaped (or round-bottomed) flask. [1 mark]
- Point 2: A thermometer is placed at the top of the still head (with its bulb adjacent to the side arm). [1 mark]
- Point 3: The condenser is attached to the side arm of the still head sloping downwards, leading to a collecting vessel (beaker/flask). [1 mark]
💡 Apparatus Setup Description
[Flask containing mixture] ➔ [Still head inserted into flask] ➔ [Thermometer at top opening]
➔ [Condenser attached to side arm, sloping downwards] ➔ [Receiver adapter/beaker at outlet]
Water must always enter the condenser at the lowest point (bottom) and leave from the top to ensure the water jacket fills completely without air pockets.
❌ Common Errors
- Leaving the condenser upright: distillation requires the condenser to be angled downwards.
- Forgetting the thermometer: without a thermometer at the junction of the still head, you cannot monitor the boiling fraction (101 °C – 103 °C).
- Sealing the system completely (e.g. stopper on collecting vessel): simple distillation must remain open to air to avoid pressure build-up.
Layer Separation and Purification
Densities, layer identification, and laboratory techniques
✅ Correct Answers
(c)(i) Diagram: A drawn beaker showing two distinct liquid layers: [1 mark]
- Top layer: Water / aqueous layer
- Bottom layer: 1-bromobutane
(c)(ii) Removing aqueous layer: Use a teat pipette (or syringe) to draw off the upper aqueous layer (or pipette out the lower layer into another container). [1 mark]
(c)(iii) Apparatus for Steps 6 & 7: Separating funnel (or dropping funnel / tap funnel). [1 mark]
📐 Density Comparison
- Density of water = 1.00 g cm⁻³
- Density of 1-bromobutane = 1.28 g cm⁻³
Since 1.28 > 1.00, 1-bromobutane is denser and sinks to the bottom. The less dense aqueous phase floats on top.
❌ Common Errors
- In (c)(i): Drawing a separating funnel instead of a beaker as specifically requested in the prompt.
- In (c)(ii): Saying "decant the top layer" — decanting does not provide clean separation of two miscible or liquid-liquid layers and loses the mark.
- In (c)(iii): Writing "burette" — burettes are for titrations, not for washing and shaking immiscible solvent layers.
🧠 Exam Technique
Always re-read the prompt: Step 4 states the distillate was "collected in a small beaker, forming two layers". Part (c)(i) asked for a diagram of the beaker, not standard separating funnel glassware!
Topics
Organic Chemistry · Inorganic Chemistry · Physical Chemistry · Topic 6: Organic Chemistry I · Topic 4: Inorganic Chemistry and the Periodic Table · Topic 9: Kinetics I · Topic 18: Organic Chemistry III
Question and mark scheme from the Edexcel A-Level Chemistry examination, AS Paper 2, June 2024. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.