A2 EVALUATIVE

For assessment use between

1 June 2011 and 14 May 2012
A2 GCE CHEMISTRY A
F326/Task 3/TASK
Practical Skills in Chemistry 2
Evaluative Task 3: Investigations involving benzoic acid
* F 3 3 4 7 5 0 6 1 2 *

Candidates answer on the Task sheet

INSTRUCTIONS TO CANDIDATES
• Write your name in capital letters, your centre number and candidate number and the
date of assessment in the boxes above.
• Read each question carefully and make sure that you know what you have to do before
starting your answer.
• Answer all parts of the Task, in the spaces provided. Additional paper may be supplied if
necessary.

INFORMATION FOR CANDIDATES

• The number of marks for each question is given in brackets [ ] at the end of each
question or part question.
• You may use a scientific calculator.
• You may use the Data Sheet for Chemistry A.
• You are advised to show all the steps in any calculations.
• Use of text books and class notes is not permitted.
• The total number of marks for this Task is 15.
• This document consists of 7 pages. Any blank pages are indicated.

FOR TEACHER’S USE

MAX. MARK

TOTAL 15

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For assessment use between 1 June 2011 and 14 May 2012

 2 For
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Answer all the parts.

Investigations involving benzoic acid

Introduction

Five students attempted to carry out a two-stage synthesis starting from ethyl benzoate,
C6H5COOCH2CH3.

There are two parts to the synthesis.

• In the first part, ethyl benzoate is hydrolysed to form crystals of benzoic acid, C6H5COOH.

• In the second part, benzoic acid is nitrated to form a mixture of products.

Part 1 – Hydrolysis of ethyl benzoate

The students were provided with the method outlined below.

Step 1 Reflux a mixture of 6.0 cm3 of ethyl benzoate (density = 1.05 g cm–3) with an
excess of aqueous sodium hydroxide (made by dissolving 2 g of sodium hydroxide
in 25 cm3 of water) for 30 minutes.

Step 2 Pour the contents from the flask into a beaker and add 1 mol dm–3 hydrochloric
acid until the solution is acidic to pH indicator paper.

Step 3 Filter the crystals under reduced pressure.

Step 4 Dissolve the crystals in the minimum of boiling water.

Step 5 Allow the solution to cool and filter the crystals of benzoic acid.

Student 1 followed the method exactly and obtained 0.021 mol of crystals of benzoic acid.

Student 2 decided not to carry out steps 2, 3, 4 and 5. Instead, he just evaporated off the water
after step 1 and was pleased that he had 4.6 g of crystals, which was more than student 1.

Student 3 decided to miss out steps 4 and 5. She was also very pleased that she had a greater
mass of crystals than student 1. However, she had a smaller mass than student 2.

Student 4 dissolved 10 g of sodium hydroxide instead of 2 g. The fourth student recognised her
mistake so she started the experiment again.

Student 5 dissolved just 1 g of sodium hydroxide instead of 2 g. This student carried on with the
experiment.

Student 6 ran out of time and filtered his solution in step 5 when it hadn’t cooled properly. He
obtained a low yield.

© OCR 2011 For assessment use between 1 June 2011 and 14 May 2012
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(a) Calculate the percentage yield of the benzoic acid obtained by student 1.

percentage yield = .............................................% [2]

(b) One reason why student 2 obtained a greater mass of crystals than student 1 was that
his product was not benzoic acid.

Give the structural formula of the organic product that student 2 prepared.

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

(c) Despite obtaining a smaller mass, the benzoic acid obtained by student 1 was purer
than the benzoic acid obtained by student 3.

Explain why student 1’s benzoic acid was purer than student 3’s benzoic acid.

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(d) Explain why student 4 did not need to start again.

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(e) Show, by calculation, that student 5 did not have an excess of sodium hydroxide.

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(f) Explain why student 6’s failure to fully cool the solution resulted in him obtaining a low
yield.

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

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Part 2 – Nitration of benzoic acid

Benzoic acid, C6H5COOH, can be nitrated with a very concentrated form of nitric acid called
‘fuming nitric acid’.

The students very carefully reacted their samples of benzoic acid with fuming nitric acid.

The students separated three organic products from the reaction mixture by chromatography.

The students suspected that the three products were structural isomers with the nitro group, NO2,
substituted at the 2-, 3- and 4-positions on the benzene ring.

The suspected structures are shown below, labelled A, B and C.

COOH COOH COOH

NO2

NO2

NO2

A B C

(a) A student measured the melting point of one of the separated products.

The student then recrystallised the sample and took the melting point of the recrystallised
product.

The student’s results are shown below.

Sample 1 melting point before recrystallisation 136–140 °C

Sample 2 melting point after recrystallisation 144–146 °C

The melting points for the three structural isomers from a database are shown below.

• 2-nitro isomer 148 °C

• 3-nitro isomer 142 °C

• 4-nitro isomer 241 °C

© OCR 2011 For assessment use between 1 June 2011 and 14 May 2012
 5 For
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(i) Why are the melting points of sample 1 and sample 2 different?

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(ii) Identify which isomer the student has analysed.

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TURN OVER FOR PART (b)

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(b) The students visited their local university and obtained spectra that they hoped would
aid the identification of A, B and C. The IR and 1H NMR spectra of one of the products
are shown below.

COOH COOH COOH

NO2

NO2

NO2

A B C

100
transmittance (%)

50

0
4000 3000 2000 1500 1000 500
wavenumber/cm–1
absorption

12 10 8 6 4 2 0
δ / ppm

© OCR 2011 For assessment use between 1 June 2011 and 14 May 2012
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After analysing the spectra, the students were confident that the product was one of the
three isomers but they were still unable to identify the compound.

(i) On the IR and 1H NMR spectra, use P to identify the peaks that give evidence for
the presence of the carboxylic acid group in the product. [2]

(ii) In a mass spectrum, what m/z value could be used to confirm that only mono-
nitration occurred in this reaction?

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

(iii) One of the students suggested that they revisit the university and obtain a 13C NMR
spectrum of the product. He told the other students that the 13C NMR spectrum
would identify the isomer.

By stating the number of peaks in the spectra of A, B and C, explain whether the
13C NMR spectrum could distinguish between the three isomers.

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............................................................................................................................ [3]

[Total: 15]

END OF TASK

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