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Benzoic Acid Preparation and Analysis

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8 views7 pages

Benzoic Acid Preparation and Analysis

Uploaded by

pjgirl707
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

PMT

4
2 Benzoic acid, C6H5COOH, is added to some foods as a preservative.

A student prepares benzoic acid as outlined below.

Step 1 The student mixes 4.00 cm3 of phenylmethanol, C6H5CH2OH, (density = 1.04 g cm−3)
with sodium carbonate and aqueous potassium manganate(VII), as an oxidising agent.
The mixture is heated under reflux.

Step 2 The resulting mixture is cooled and then acidified with concentrated HCl .
Impure crystals of benzoic acid appear.

Step 3 The student recrystallises the impure crystals to obtain 1.59 g of pure benzoic acid.

(a) In Step 1, sodium carbonate, Na2CO3, makes the reaction mixture alkaline.

Write an ionic equation to show how carbonate ions form an alkaline solution in water.

.............................................................................................................................................. [1]

(b) In Step 2, explain why the mixture must be acidified so that crystals of benzoic acid appear.

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(c) Write the overall equation for the preparation of benzoic acid from phenylmethanol.

Use [O] for the oxidising agent.

.............................................................................................................................................. [1]

(d) Calculate the percentage yield of benzoic acid.

Give your answer to 3 significant figures.

percentage yield = ...................................................... % [3]


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(e) In Step 3, describe how the student can recrystallise the impure crystals to obtain pure
benzoic acid.

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© OCR 2019 Turn over


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3 This question is about elements and compounds in Group 14 (Group 4) of the periodic table.

(a) There are four oxides of lead: PbO, PbO2, Pb2O3 and Pb3O4.

A student carries out an experiment to identify an unknown lead oxide, which is one of the
four oxides of lead shown above.

The student plans to reduce the unknown lead oxide to lead by heating the lead oxide in a
stream of methane gas, CH4. The apparatus is shown below.

dish containing lead oxide


tube

methane gas

heat

Student’s method

• Weigh an empty dish.


Add the lead oxide to the dish and reweigh.

• Set up the apparatus and pass methane gas through the tube as shown.
Heat the dish for 10 minutes.

• Pass cold air through the tube to cool the dish and contents.

• Weigh the dish and contents.

(i) Write the equation for the reduction of Pb2O3 with CH4.

...................................................................................................................................... [1]

(ii) The student uses safety glasses and a lab coat.

State, with a reason, one other important safety precaution the student should take when
carrying out this experiment.

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(iii) The student was not sure that all the oxygen had been removed from the lead oxide.

Suggest two modifications that the student could make to their method to be confident
that all the oxygen had been removed. Explain your reasoning.

1 ........................................................................................................................................

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2 ........................................................................................................................................

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[2]

(iv) The student makes suitable modifications to the method and repeats the experiment to
obtain the accurate results shown below.

Mass of dish / g 8.364


Mass of dish + lead oxide / g 11.818
Mass of dish + lead at end of experiment / g 11.496

Calculate the empirical formula of the lead oxide.

empirical formula = ......................................................... [2]

(b) SiO2 and CO2 are oxides of other Group 14 (Group 4) elements.

Solid SiO2 melts at 2156 °C. Solid CO2 melts at −56 °C.

Suggest the type of lattice structure in solid SiO2 and in solid CO2 and explain the difference
in melting points in terms of the types of force within each lattice structure.

Structure in SiO2(s) ...................................................................................................................

Structure in CO2(s) ...................................................................................................................

Explanation ...............................................................................................................................

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4 Dettol® is a disinfectant containing the antiseptic chloroxylenol, shown below.

OH

H 3C CH3

Cl
chloroxylenol

(a) Chloroxylenol is a weak Brønsted–Lowry acid.

(i) What is the systematic name of chloroxylenol?

...................................................................................................................................... [1]

(ii) Predict the number of peaks in a 13C NMR spectrum of chloroxylenol.

...................................................................................................................................... [1]

(iii) Name the functional group responsible for the acidity of chloroxylenol and describe a
simple test which would confirm the presence of this group.

Functional group ................................................................................................................

Test ....................................................................................................................................

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...................................................................................................................................... [2]

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(iv) A student measures the pH of the contents in a bottle of Dettol® as 5.14.

The label on the bottle shows the percentage of chloroxylenol in Dettol® as 4.80%
i.e. 100 cm3 of Dettol® contains 4.80 g of chloroxylenol.

Assume the following:


• Chloroxylenol is the only acidic component in Dettol®.
• Chloroxylenol is a weak monobasic acid.
• The density of Dettol® is 1.00 g cm−3.

Write the equation, using molecular formulae, for the acid dissociation of chloroxylenol.

Calculate the acid dissociation constant, Ka, for chloroxylenol.

Ka = .......................................... mol dm−3 [5]

© OCR 2019 Turn over

Common questions

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The systematic name of chloroxylenol is 4-chloro-3,5-dimethylphenol. It is effective as an antiseptic due to its ability to disrupt microbial cell walls, thus killing bacteria and viruses. This property makes it a key ingredient in disinfectants such as Dettol®.

Given the pH of Dettol® (5.14) and chloroxylenol concentration (4.80 g/100 cm³; assume volume 100 cm³ and density 1.00 g/cm³, thus 0.0480 mol/L), first calculate the concentration of hydrogen ions: [H+] = 10^-5.14 ≈ 7.24 x 10^-6 mol/L. For a weak acid, HA ⇌ H+ + A-, use [H+] = [A-] and [HA] initial = 0.0480 mol/L. Ka = [H+]^2/[HA] ≈ (7.24 x 10^-6 mol/L)^2 / (0.0480 mol/L - 7.24 x 10^-6 mol/L) ≈ 1.09 x 10^-9 mol/L.

Recrystallization involves dissolving impure crystals in a minimum amount of hot solvent in which the impurities are more soluble than the benzoic acid. On cooling, benzoic acid recrystallizes due to decreased solubility, leaving impurities in solution. The crystals are then filtered, washed with a small amount of cold solvent, and dried.

There are five peaks expected in the 13C NMR spectrum of chloroxylenol. This accounts for the different carbon environments: one for the carbon bonded to the chlorine atom, two different carbons in the meta positions (relative to OH), one para carbon, and two equivalent methyl carbons.

An essential safety precaution is performing the reaction in a fume hood. This is to prevent the inhalation of toxic lead dust and methane gas, which is flammable and poses a risk of explosion in confined spaces.

SiO2 forms a giant covalent (network) structure, where each silicon atom is covalently bonded to four oxygen atoms in a tetrahedral arrangement, leading to a high melting point (2156°C) due to strong Si-O bonds. In contrast, CO2 is molecular with weak intermolecular forces (van der Waals), resulting in a low melting point (-56°C)

Sodium carbonate serves to maintain an alkaline environment during the oxidation of phenylmethanol. In water, sodium carbonate dissociates to form carbonate ions (CO3^2-), which react with water to produce bicarbonate ions (HCO3^-) and hydroxide ions (OH^-). These hydroxide ions are responsible for making the solution alkaline.

Acidification is necessary to protonate the benzoate ions that form in the alkaline reaction mixture. When concentrated HCl is added, it provides hydrogen ions (H+) which convert soluble benzoate salts to insoluble benzoic acid, causing it to precipitate as crystals.

First, calculate the mass of phenylmethanol used: mass = volume x density = 4.00 cm³ x 1.04 g/cm³ = 4.16 g. Determine moles of phenylmethanol using its molecular weight (C6H5CH2OH), approximately 108 g/mol: moles = mass/molar mass = 4.16 g/108 g/mol ≈ 0.0385 mol. Assuming complete conversion, theoretical yield of benzoic acid is 0.0385 mol x 122 g/mol ≈ 4.697 g (molecular weight of C6H5COOH ≈ 122 g/mol). Actual yield is 1.59 g. Percentage yield = (actual/theoretical) x 100 ≈ (1.59 g/4.697 g) x 100 = 33.8%

Calculate the mass of lead oxide used: mass of lead oxide = mass of dish + lead oxide - mass of dish = 11.818 g - 8.364 g = 3.454 g. Mass of lead after reduction: 11.496 g - 8.364 g = 3.132 g. Oxygen mass = 3.454 g - 3.132 g = 0.322 g. Divide by atomic masses (Pb = 207.2, O = 16): Moles of Pb = 3.132 g/207.2 g/mol ≈ 0.0151 mol, moles of O = 0.322 g/16 g/mol = 0.0201 mol. Empirical ratio: Pb:O = 0.0151:0.0201 ≈ 3:4, resulting in Pb3O4.

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