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 question

Question

The question presents a 9-step laboratory procedure for synthesising 1-bromobutane from butan-1-ol using sodium bromide and concentrated sulfuric acid. An apparatus diagram shows a pear-shaped flask submerged in an ice-water bath containing butan-1-ol, sodium bromide, and water, fitted vertically with a condenser, a still head, and a tap funnel containing concentrated sulfuric acid. Sub-questions ask for: (a)(i) reasons for the condenser and still head in steps 1 and 2; (a)(ii) the oxidising agent responsible for unwanted redox side reactions; (a)(iii) one unwanted inorganic and one organic product from these redox reactions; (a)(iv) why ice prevents these redox products; (b) how to rearrange the apparatus for distillation; (c)(i) a labelled diagram of the beaker containing two layers before separation given densities of water (1.00 g cm⁻³) and 1-bromobutane (1.28 g cm⁻³); (c)(ii) how to remove the aqueous layer; and (c)(iii) the apparatus used to separate the organic layer in steps 6 and 7.
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 The mark scheme provides the marking points: 5(a)(i) Condenser prevents loss of volatile reactants/products or prevents escape of harmful gases (1 mark); still head prevents build-up of pressure/explosion (1 mark). 5(a)(ii) Concentrated sulfuric acid / H2SO4 (1 mark). 5(a)(iii) Inorganic: Br2 or SO2 (1 mark); Organic: butanal or butanoic acid (1 mark). 5(a)(iv) Lower temperature means fewer collisions have energy greater than or equal to activation energy, decreasing reaction rate (1 mark). 5(b) Condenser removed and still head placed in pear-shaped flask (1 mark); thermometer placed in top of still head (1 mark); condenser placed at the side/downward angle with a receiver beaker below (1 mark). 5(c)(i) Diagram showing water as the upper layer and 1-bromobutane as the lower layer in a beaker (1 mark). 5(c)(ii) Use a teat pipette or syringe to remove the upper aqueous layer (1 mark). 5(c)(iii) Separating funnel / dropping funnel (1 mark).

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

📌 What this question tests

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.
Question 5(a)(i) · 2 Marks

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).
Mark breakdown: 1 mark for condenser role + 1 mark for still head role preventing pressure build-up.
Question 5(a)(ii) & (iii) · 3 Marks

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.

Mark breakdown: (a)(ii) 1 mark; (a)(iii) 1 mark for inorganic redox product + 1 mark for organic redox product.
Question 5(a)(iv) · 1 Mark

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:

  1. Energetics: Lower temperature means fewer particles have the activation energy needed to react.
  2. Rate: Low temperature dramatically slows down the rate of the unwanted side reaction.
Mark breakdown: 1 mark for linking lower temperature to activation energy collision frequency or decreased reaction rate.
Question 5(b) · 3 Marks

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

Standard Simple Distillation Layout:
[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.
Mark breakdown: 3 marks total (1 mark for still head on flask, 1 mark for thermometer in still head, 1 mark for downward condenser).
Question 5(c)(i), (ii) & (iii) · 3 Marks

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!

Mark breakdown: (c)(i) 1 mark for correct layers labelled; (c)(ii) 1 mark for pipette/syringe; (c)(iii) 1 mark for separating funnel.

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.