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 question

Question

A multi-part organic chemistry question about extracting and purifying benzoic acid from a mixture. It outlines 9 laboratory steps, followed by questions on completing a chemical equation, describing pressure release in a separating funnel, explaining density layers, washing ether, precipitation by HCl, drawing vacuum filtration apparatus, calculating moles and number of molecules of benzoic acid, and comparing melting temperature ranges.
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 The mark scheme for the benzoic acid extraction question. It provides the balanced chemical equation, instructions for releasing pressure (invert and open tap), explanations for density and washing, the mechanism of precipitation, a diagram of Buchner filtration, full calculation steps for finding the number of molecules of benzoic acid, and criteria for evaluating the melting point range.

How to answer it

Extracting and Purifying Benzoic Acid Study Guide

What this question tests

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.

Marks: 2 | Awarded for: (1) correct sodium benzoate formula/structure, (1) remainder of equation ( H₂O + CO₂ ).

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.

Marks: 1 | Awarded for: Mentioning both inversion and opening the tap.

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.

Marks: 1 | Awarded for: Stating water/aqueous layer has a higher density than ether.

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.

Marks: 1 | Awarded for: Recognizing that sodium benzoate may have dissolved in the ether layer.

Part (e): Precipitation Mechanism

Why hydrochloric acid precipitates benzoic acid

✅ Correct Answer

  1. The benzoate ion is protonated by the hydrochloric acid.
  2. 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).

Marks: 2 | Awarded for: (1) Protonation of benzoate ion, (1) Lower solubility of the uncharged benzoic acid product.

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).

Marks: 2 | Awarded for: (1) Büchner/side-armed flask connected to a vacuum source, (1) Büchner funnel with flat filter paper.

Part (g): Solubility & Stoichiometry Calculation

Calculating maximum dissolved molecules

📐 Step-by-Step Calculation

  1. Find mass in 50.0 cm³:
    Mass = (1.70 g / 1000 cm³) × 50.0 cm³ = 0.0850 g
  2. 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
  3. 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.

Marks: 3 | Awarded for: (1) correct mass or mole scaling, (1) correct evaluation of moles, (1) multiplication by Avogadro constant to find molecules.

Part (h): Purity Analysis via Melting Point

Comparing experimental range to literature value

✅ Correct Answer

  1. The melting temperature range is wider (or "not sharp") compared to a pure sample.
  2. 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.

Marks: 2 | Awarded for: (1) Noting a wide/non-sharp melting range, (1) Explaining that the melting point is lower due to impurities.

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.