16 Organic synthesis

OCR Chemistry A Exam-style questions

1 The diagram below shows apparatus commonly used when synthesising organic
chemicals:

a Name the heating technique that could be carried out using the apparatus above.

(1 mark)

b Name the piece of apparatus labelled X.

(1 mark)

c Many organic reactions are slow, so must be heated to improve the rate of
reaction.
Explain why the piece of apparatus labelled X must be used, rather than an
open conical flask over a Bunsen burner.

(1 mark)

d Would you use the apparatus set-up shown above to oxidise propan-1-ol into
propanal? Explain your answer.

(2 marks)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

2 2-bromopentane can be prepared by refluxing an alcohol with aqueous sodium

bromide and sulfuric acid.
a Write an equation for this reaction, using structural formulae.

(2 marks)

b At the end of this reaction, the contents of the round-bottomed flask are
shaken with sodium carbonate solution and effervescence is observed.
i What is the purpose of adding sodium carbonate solution?

(1 mark)

ii What gas is being produced?

(1 mark)

c The contents of the flask then settle into two layers, an organic layer and an
aqueous layer. Name the piece of apparatus used to separate these two layers.

(1 mark)

d Anhydrous magnesium sulfate is added to the separated organic layer.

i Give the formulae of magnesium sulfate.

(1 mark)

ii What is the purpose of adding anhydrous magnesium sulfate?

(1 mark)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

e The apparatus below shows the final process used to separate

2-bromopentane from any other unwanted organic products.

i Name this process.

(1 mark)

ii Suggest how the thermometer shown in the diagram above would allow
you to check the purity of your product.

(1 mark)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

3 Safranal, shown below, is the organic compound primarily responsible for the
aroma of the spice saffron:

a Give the molecular formula of safranal.

(1 mark)

b i Name the two functional groups that are present in safranal.

(2 marks)
ii Draw the structure of the alcohol that could be used to synthesise safranal.

(1 mark)
c i Is safranal saturated or unsaturated?
Explain your answer, making reference to any relevant bonds.

(1 mark)

ii Draw the product formed when safranal undergoes an addition reaction

with excess hydrogen gas.

(2 marks)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

iii Name a heterogeneous catalyst that could be used for this addition
reaction.

(1 mark)

d Crocetin, shown below, is another organic compound found within saffron.

This compound is responsible for the orange colour of saffron.

Name the two functional groups that are present in this molecule.

(2 marks)

e What is the minimum number of bromine molecules required to completely

react with one molecule of crocetin?

(1 mark)

f Look at the central double bond in this molecule of crocetin. Is this molecule
the cis or trans form around this central double bond? Explain your answer.

(2 marks)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

4 Consider the following series of reactions and answer the questions that follow.

a Suggest what type of reaction is represented by the conversion of A into B.

(1 mark)

b Draw the organic product in Box C that is made when B reacts with acidified
potassium dichromate(VI).

(1 mark)

c What colour change will be observed when B is converted into C?

(1 mark)

d What type of heating technique is needed for the conversion of B into C?

(1 mark)

e What type of reaction is represented by the conversion of A into D?

(1 mark)

f What colour change will be observed when D is converted into E?

(1 mark)

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 16 Organic synthesis
OCR Chemistry A Exam-style questions

g What type of reaction is represented by the conversion of D into E?

(1 mark)

h i What reagent and conditions are required for the conversion of D into B?

(1 mark)

ii Name the other alcohol that would also be made in this conversion.

(1 mark)

5 Propanoic acid can be made from 1-bromopropane in a two-step reaction pathway:

a Draw the structure of compound B in the box above. (1 mark)

b Give the reagent needed for the conversion of 1-bromopropane into compound B.

(1 mark)

c Suggest the reagent and conditions needed to convert compound B into

propanoic acid.

(2 marks)

d What type of reaction is represented by the conversion of compound B into

propanoic acid?

(1 mark)

e How would using 1-chloropropane, rather than 1-bromopropane, affect the

overall atom economy of this reaction? Explain your answer.

(2 marks)

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