Edexcel A-Level Chemistry Paper 3, November 2020: Question 5
14 marks · Medium difficulty · Open Response
Extract and purify benzoic acid from a mixture including writing a neutralization equation, describing experimental purification techniques, and calculating the maximum number of molecules soluble in a given volume.
Practise this questionQuestion
Question text
5 This question is about extracting benzoic acid from a mixture of benzoic acid, C6H5COOH,
and phenol, C6H5OH.
The following steps were carried out.
Step 1 A suitable mass of the mixture was placed in a separating funnel and some
ether added. The funnel was shaken to dissolve the mixture.
Step 2 Aqueous sodium hydrogencarbonate was added to the separating funnel,
and the contents shaken.
Step 3 Once the reaction was complete, the two layers were allowed to separate.
Step 4 The lower aqueous layer was removed and placed in a beaker.
Step 5 The ether layer in the separating funnel was washed with deionised water
and the washings added to the beaker.
Step 6 Hydrochloric acid was added to the aqueous solution in the beaker to
precipitate the benzoic acid.
Step 7 The impure benzoic acid was filtered under reduced pressure.
Step 8 The impure benzoic acid was purified by recrystallisation.
Step 9 The melting temperature of the purified benzoic acid was measured and
o
compared with the literature value of 122 C.
(a) Complete the equation for the reaction between benzoic acid and
sodium hydrogencarbonate.
(2)
O OH
C
+ … → … + … + …
(b) In Step 2 there is a pressure build-up in the separating funnel.
Describe how you would lower the pressure.
(1)
(c) State why, in Step 4, the aqueous layer was the lower of the two layers.
(1)
(d) Give a reason why, in Step*P62670A01432*5, the ether layer was washed with deionised water.
(1)
(e) Explain why the addition of hydrochloric acid in Step 6 results in the precipitation
of benzoic acid.
(2)
(f ) Draw a diagram of the apparatus used in Step 7 to filter under reduced pressure.
(2)
(g) Benzoic acid can be purified in Step 8 because of its high solubility in hot water
and low solubility in cold water.
Calculate the maximum number of benzoic acid molecules that can dissolve in
50.0 cm3 of cold water if the solubility is 1.70 g per 1000 cm3.
(3)
(h) The melting temperature range of the purified benzoic acid in Step 9 was
o
116–121 C.
Compare this result with the literature value, giving a reason for any differences.
*P62670A01532* (2)
(Total for Question 5 = 14 marks)
Mark scheme
Show the mark scheme
How to answer it
Extracting and Purifying Benzoic Acid Study Guide
This question covers organic extraction techniques, functional group chemistry (acid-base reactions of carboxylic acids), practical apparatus setups (reduced pressure filtration), stoichiometry calculations involving Avogadro's constant, and purity analysis using melting point determinations.
Part (a): Neutralisation Equation
Reaction between benzoic acid and sodium hydrogencarbonate
✅ Correct Answer
Organic structure of sodium benzoate ( C₆H₅COO⁻Na⁺ or showing ionic bond) + H₂O + CO₂
💡 Key Knowledge
Carboxylic acids are strong enough to react with weak bases like NaHCO₃ , releasing carbon dioxide gas. Phenol (the other component in the mixture) is too weakly acidic to react with sodium hydrogencarbonate, allowing separation.
❌ Common Errors
Incorrectly writing the carboxylate sodium bond as O-Na with a covalent bond instead of showing the ionic species, or forgetting state symbols/byproducts.
Part (b): Separating Funnel Pressure
Managing pressure build-up
✅ Correct Answer
Invert the funnel and then open the tap.
🧠 Exam Technique
Always state the two-step action clearly: invert first so that the tap points away from you and others, then open the tap to release accumulated CO₂ gas.
Part (c): Layer Densities
Position of the aqueous layer
✅ Correct Answer
Water is more dense than ether (the organic layer).
❌ Common Errors
Writing that water is "insoluble" instead of referring explicitly to density differences.
Part (d): Washing the Ether Layer
Purpose of washing with deionised water
✅ Correct Answer
To remove any soluble impurities (such as dissolved sodium benzoate) that partitioned into the ether layer.
💡 Key Knowledge
Organic solvents can retain small amounts of aqueous solutes. Washing ensures maximum transfer of the desired salt into the aqueous extract.
Part (e): Precipitation Mechanism
Why hydrochloric acid precipitates benzoic acid
✅ Correct Answer
- The benzoate ion is protonated by the hydrochloric acid.
- Benzoic acid is substantially less soluble in cold water than its sodium salt, causing it to precipitate out.
🧠 Exam Technique
To secure both marks, you must link the chemical change (protonation to form the neutral acid) to the physical property change (decreased aqueous solubility).
Part (f): Reduced Pressure Filtration
Apparatus for Step 7
✅ Correct Answer
A Büchner flask connected via a side-arm to a vacuum pump/water aspirator, fitted with a Büchner funnel containing flat filter paper.
❌ Common Errors
Drawing a standard conical flask or specifying a "fluted filter paper" (which is used for gravity filtration, not vacuum filtration).
Part (g): Solubility & Stoichiometry Calculation
Calculating maximum dissolved molecules
📐 Step-by-Step Calculation
- Find mass in 50.0 cm³:
Mass = (1.70 g / 1000 cm³) × 50.0 cm³ = 0.0850 g - Find moles of benzoic acid ( C₆H₅COOH ):
Molar mass = (6×12.0) + (5×1.0) + 12.0 + (16.0×2) + 1.0 = 122.0 g mol⁻¹
Moles = 0.0850 g / 122.0 g mol⁻¹ = 6.967 × 10⁻⁴ mol - Convert moles to number of molecules:
Molecules = 6.967 × 10⁻⁴ × 6.02 × 10²³ = 4.19 × 10²⁰
❌ Common Calculation Traps
Do not use 1 sf in final answers. Avoid excessive significant figures (6+ SF); keep your final answer to 3 significant figures matching standard data conventions.
Part (h): Purity Analysis via Melting Point
Comparing experimental range to literature value
✅ Correct Answer
- The melting temperature range is wider (or "not sharp") compared to a pure sample.
- The melting temperature is lower than the literature value ( 122 °C ) due to the presence of impurities (such as unreacted phenol or water).
💡 Key Knowledge
Impurities disrupt the regular crystal lattice of a solid, weakening intermolecular forces. This causes melting to occur over a broader range and at a lower temperature than the pure reference value.
Topics
Organic Chemistry · Core Practicals · Physical Chemistry · Core Practical 7: Identify unknown organic liquids and inorganic solids · Core Practical 15: Analyse organic and inorganic unknowns · Core Practical 16: Synthesise aspirin from 2-hydroxybenzoic acid · Topic 18: Organic Chemistry III · Topic 17: Organic Chemistry II · Topic 5: Formulae, Equations and Amounts of Substance
Question and mark scheme from the Edexcel A-Level Chemistry examination, Paper 3, November 2020. QuestionVault is an independent revision resource; questions remain the copyright of the awarding body.