Practical Endorsement GCE Chemistry

PAG6 Synthesis of an organic solid

6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

This is a suggested practical activity that can be used as part of teaching the GCE Chemistry A and B (Salters)
specifications, and in part helps to fulfil the requirements of the Practical Endorsement. These are not
coursework tasks, and there is no requirement to use these activities. You may modify these activities to suit
your learners and centre. Alternative activities are available from, for example, RSC LearnChemistry, CLEAPSS and
publishing companies. Support for mapping activities to the requirements of the Practical Endorsement is
available from OCR – see https://www.ocr.org.uk/positiveaboutpractical or email us at PASS@ocr.org.uk.

OCR recommendations:
 Before carrying out any experiment or demonstration based on this guidance, it is the responsibility of
teachers to ensure that they have undertaken a risk assessment in accordance with their employer’s
requirement, making use of up-to-date information and taking account of their own particular
circumstances. Any local rules or restrictions issued by the employer must always be followed.
 Use CLEAPSS resources (http://www.cleapss.org.uk) when carrying out risk-assessments.
 Centres should trial experiments in advance of giving it to learners. Centres may choose to make
adaptations to this practical, but should be aware that may affect the criteria covered. It is always
possible to split tasks to suit your centre.
 Centres should retain their trial results along with their other documentation records.

This activity has been designed for learners to carry out a risk assessment prior to carrying out the practical
activity – these should be reviewed before any practical work is carried out. A risk assessment for the
activity is included on the last page of the learner sheets, and can be used should the learners’ risk
assessment prove inadequate.

NOTE: This is a lengthy activity, and can be split into convenient sections if required – see Notes.

6.2 Preparation of benzoic acid TEACHER/TECHNICIAN

Introduction
In this experiment, students will prepare benzoic acid, C6H5COOH, by alkaline hydrolysis of an ester, following by
acidification.

1. Alkaline hydrolysis of an ester, methyl benzoate (C6H5COOCH3), to form a solution of sodium benzoate
(C6H5COONa), a salt of benzoic acid.
2. Acidification of sodium benzoate to form benzoic acid.

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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

Aims and Skills

 To carry out a two-step synthesis, purification and identification of benzoic acid
 To carry out a risk assessment
 To heat a reaction mixture under reflux
 To purify an organic solid by recrystallization
 To use melting point apparatus
 To use thin layer or paper chromatography

Intended class time

 2 hours and time to conduct risk assessments
 The activity could be shortened by omitting the TLC stage and carrying out chromatography in another
activity, e.g. chromatography of amino acids using paper chromatography. You would then need to adjust
the criteria being assessed in this activity.

Practical Skills
 1.2.1(b) safely and correctly use a range of practical equipment and materials
 1.2.1(c) follow written instructions
 1.2.1(d) make and record observations/measurements
 1.2.1(e) keep appropriate records of experimental activities
 1.2.1(f) present information and data in a scientific way
 1.2.1(h) use online and offline research skills including websites, textbooks and other printed scientific
sources of information
 1.2.1(i) correctly cite sources of information
 1.2.1(j) use a wide range of experimental and practical instruments, equipment and techniques
appropriate to the knowledge and understanding included in the specification.
 1.2.2(a) use of appropriate apparatus to record a range of measurements (to include mass, time, volume
of liquids and gases, temperature)
 1.2.2(b) use of a water bath or electric heater or sand bath for heating
 1.2.2(d) use of laboratory apparatus for a variety of experimental techniques including: (ii) heating under
reflux, including setting up glassware using retort stand and clamps; (iv) filtration, including use of fluted
filter paper, or filtration under reduced pressure
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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

 1.2.2(g) purification of: (i) a solid product by recrystallisation

 1.2.2(h) use of melting point apparatus
 1.2.2(i) use of thin layer or paper chromatography
 1.2.2(k) safely and carefully handling solids and liquids, including corrosive, irritant, flammable and toxic
substances

CPAC
(1) Follows written procedures
(3) Safely uses a range of practical equipment and materials
(4) Makes and records observations
(5) Researches, references and reports

Links to Specifications
Chemistry A
 6.1.3(d) hydrolysis of esters (ii) in hot aqueous alkali to form carboxylate salts and alcohols
 6.2.5(a) the techniques and procedures used for the preparation and purification of organic solids
involving use of a range of techniques (see also 4.2.3 a) including:
(i) organic preparation
- use of Quickfit apparatus
- distillation and heating under reflux
(ii) purification of an organic solid
- filtration under reduced pressure
- recrystallization
- measurement of melting points
Chemistry B
 WM(e) techniques and procedures for making a solid organic product and for purifying it using filtration
under reduced pressure and re-crystallisation (including choice of solvent and how impurities are
removed); techniques and procedures for melting point determination and thin layer chromatography;
 PL(m) the hydrolysis of esters and amides by both aqueous acids and alkalis, including salt formation
where appropriate

Mathematical Skills
 Mathematical skills are required in the recording of the data and calculations. These steps require the
appropriate application of the following mathematical skills:
 M0.0 Recognise and make use of appropriate units in calculations
 M0.2 Use ratios, fractions and percentages

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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

Chemicals
The following chemicals will be required, labelled as shown in the first column of each table.

Identity / amount required

Label Hazard information
per learner or group
methyl benzoate,
WARNING
C6H5COOCH3(l)
methyl benzoate Harmful if swallowed. May cause skin
irritation and serious eye irritation.
c. 2 cm3
2.0 mol dm3 aqueous DANGER
–3
2.0 mol dm sodium hydroxide, NaOH(aq) Causes severe skin burns and eye
NaOH(aq) damage
c. 10 cm3 Wear splash-proof goggles
2.00 mol dm–3 aqueous
2.00 mol dm–3 hydrochloric acid, HCl(aq) Currently not classified as hazardous at this
HCl(aq) concentration
c. 20 cm3

DANGER
ethanol, C2H5OH(l) Highly flammable liquid and vapour.
Ethanol
c. 10 cm3 IDA is also: Harmful if swallowed. May
cause damage to organs.

Currently not classified as hazardous at this

methyl orange 0.1% methyl orange
concentration
indicator indicator
See CLEAPSS Recipe Book 46

For Part 3 (TLC) only:

Identity / amount
Label required per learner Hazard information
or group
methyl benzoate,
WARNING
C6H5COOCH3(l)
methyl benzoate Harmful if swallowed. May cause skin
irritation and serious eye irritation.
c. a few crystals

benzoic acid (pure) DANGER

benzoic acid,
Causes skin irritation, serious eye
C6H5COOH(s)
benzoic acid (from Part 2) damage, damage to organs (lungs)
through prolonged or repeated
c. a few crystals
benzoic acid (from Part 2) exposure (inhalation)

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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

Identity / amount
Label required per learner Hazard information
or group

DANGER
200:100:1 Highly flammable liquid and vapour.
cyclohexane:ethyl Causes serious eye irritation. May be
aspirin / benzoic acid ethanoate: glacial fatal if swallowed and enters airways.
chromatography solvent ethanoic acid May cause drowsiness or dizziness.
Repeated exposure may cause skin
c. 10 cm3 dryness or cracking.

iodine crystals WARNING

I2(s) Harmful in contact with skin. Harmful
c. a few crystals if inhaled. Very toxic to aquatic life.

Equipment
Parts 1–2 Preparation, recrystallisation and melting point
 eye protection
 access to balance accurate to two decimal places
 measuring cylinder (10 cm3)
 dropping pipettes
 Quickfit apparatus:
o pear-shaped or round-bottom flask (50 cm3)
o Liebig condenser and tubing
 anti-bumping granules
 wash bottle with distilled (or deionised) water
 250 cm3 beaker
 glass rod
 apparatus for filtration under reduced pressure and appropriate filter paper
 boiling tube
 sample tube and lid
 ice
 glass marker pen
 capillary tubes/melting point tubes
 Bunsen burner
 spatula
 watchglasses
 melting point apparatus – either a commercially available apparatus, or using a Theile tube (see e.g.
https://www.youtube.com/watch?v=6G2x6SjQAh4).

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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

Part 3: Chromatography
Note: Optional - chromatography could be completed as a separate activity at a different stage of the course. This
activity will then not fulfil specification point 1.2.2(i).
 UV light source
 watch glasses
 dropping pipette
 thin layer chromatography plate (silica-coated, fluorescent), cut to fit into 100 cm 3 beakers
 beaker (100 cm3)
 watch glass or other suitable cover for the beaker
 (if using iodine as locating agent, an additional beaker and cover will be required)
 pencil
 melting point tubes drawn out into a fine capillary tube in Bunsen flame OR very fine glass dropping
pipettes OR fine artist paint brushes

Health and Safety

 Health and safety should always be considered by a centre before undertaking any practical work. A full
risk assessment of any activity should always be undertaken.
 It is advisable to check the CLEAPSS website (http://www.cleapss.org.uk) in advance of undertaking the
practical tasks.
 Learners should wear eye protection throughout – some chemicals require splash-resistant goggles/face
shields.
 Use of gloves should be considered – check CLEAPSS Hazcards for particular guidance on the chemicals
used and Guidance Leaflet 210 for full details.

Notes
 Learners are asked to conduct a risk assessment prior to carrying out the procedure. Learners should
research the reagents they are using and the products formed to identify associated hazards, and
consider any risks involved in the procedure. Make sure that learners do not carry out the procedure
before you are satisfied that they are fully aware of all risks and appropriate precautions. A risk
assessment sheet is available at the end of the learner’s sheets.
 In a lengthy procedure like this one it is important that learners are asked to consider what they are doing
at each stage, rather than simply following the process like a recipe. This is particularly important in the
recrystallisation in Part 2, and with regard to the chemistry of the reactions performed in Parts 1. Learners
should be challenged to consider what is happening at each stage of the process in terms of removing
impurities.

Trial results, answers to analysis and extension questions

OCR recommends that this practical is trialled by the centre in advance of giving it to learners. We advise that the
trail results are kept as part of centre records for assessing the Practical Endorsement.

Analysis of results – Part 1 – using trial data

1. Actual yield = 1.56 g
M ( benzoic acid )
theoretical yield = V(methyl benzoate) x (methyl benzoate) x M ( methyl benzoate)

122.0
= 2.0 x 1.09 x 136. 0
= 1.96 g

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 Practical Endorsement GCE Chemistry
PAG6 Synthesis of an organic solid
6.2 Preparation of benzoic acid
TEACHER/TECHNICIAN

actual yield 1.56

percentage yield = theoretical yield x 100% = 1. 96 x 100% = 80% (2 sig. fig.)

2. melting point of benzoic acid – 120 C (source: www.chemspider.com)

Analysis of results questions – Part 2

1. Spots with similar Rf values to pure benzoic acid were present in the samples from Part 1 and 2, indicating
the synthesis was successful.
2. There was a spot with a similar Rf value to the methyl benzoate in the Part 1 sample, but not in the Part 2
sample, indicating the recrystallization was successful at purifying the benzoic acid from the methyl
benzoate.

Answers to Extension Opportunities

Answers to the extension questions on the student sheet are available on Interchange in the Science Coordinator
Materials area.

Recording
As evidence for the Practical Endorsement, learners:
 should not need to re-draft their work, but rather keep all of their notes as a continuing record of their
practical work, dating their work clearly,
 should record any observations made in full detail, clearly identifying what was observed,
 should record any measurements taken to the number of decimal places (resolution) appropriate for the
apparatus used. This should be recorded clearly in a table format, or clearly identified with appropriate
units,
 should record any modifications to supplied procedures, including their own risk assessments and
methods where appropriate.

In preparation for assessment of practical work in the written examinations, and to help learners develop their
understanding of the underlying chemical theory, learners:
 should answer all ‘Analysis’ and ‘Extension Opportunities’ questions,
 should show full workings in calculations, and final answers to the appropriate number of significant
figures.
This work can be incorporated into learners’ practical work records.

Document updates
v1.0 1 June 2015
v2.0 15 January 2016
v2.1 31 August 2016
v3.0 17 February 2020
Original version.
Reviewed - risk assessment procedure rewritten to allow learners to complete
individual risk assessments before commencing work. Analysis and extension
opportunities consolidated, diagrams updated, other minor clarifications and
standardisation of formatting and terminology. Skills/techniques used have not
been modified – updated links to specification learning outcomes, and updated
Practical Skills links to match PAG Tracker. Practical procedures have been
clarified.
Change to ‘Records’ heading in leaner sheet.
Addition of skills 1.2.1(f), 1.2.1(h), 1.2.1(i) and CPAC5. Minor reordering.
Answers removed from teacher document and added to separate file on
Interchange. No other changes have been made.

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