Name: ________________________

A-Level Chemistry Organic

Practical Questions Class: ________________________
Question Paper
Date: ________________________

Time: 122 minutes

Marks: 99 marks

Comments:

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 This question is about the analysis of organic compounds.
1.
For each pair of compounds in parts (a) and (b), give a reagent (or combination of
reagents) that could be added separately to each compound in a single reaction to
distinguish between them.

State what is observed in each case.

(a) CH3CH2CH2CHO and CH3CH2CH(OH)CH3

Reagent(s) _________________________________________________________

Observation with CH3CH2CH2CHO ______________________________________

___________________________________________________________________

Observation with CH3CH2CH(OH)CH3 ____________________________________

___________________________________________________________________
(3)

(b) Cyclohexane and cyclohexene

Reagent(s) _________________________________________________________

Observation with cyclohexane __________________________________________

___________________________________________________________________

Observation with cyclohexene __________________________________________

___________________________________________________________________
(3)

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(c) The table below gives the precise relative molecular masses (Mr) of some organic
compounds measured using high resolution mass spectrometry.

Molecular formula C5H12 C5H10 C 6H 6

Mr 72.1416 70.1260 to be calculated

Use these data to find the relative atomic masses (Ar) of hydrogen and carbon. Give your
answers to 4 decimal places.

Use these calculated Ar values to find the relative molecular mass (Mr) of C6H6 Give your
answer to 4 decimal places.

Ar of hydrogen ____________________

Ar of carbon ______________________

Mr of C6H6 ______________________
(3)
(Total 9 marks)

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 A student plans a series of chemical tests to confirm the identities of four organic liquids.
2.

This is the student’s method.

To separate test tubes containing samples of each liquid:

Test 1 add potassium dichromate(VI) solution and warm gently

Test 2 add Fehling’s solution and cool in iced water

Test 3 add sodium hydrogencarbonate solution and test any gas produced with a lighted splint

Test 4 add bromine water and shake at room temperature.

(a) Identify the missing reagent needed in Test 1.

___________________________________________________________________
(1)

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(b) In addition to the missing reagent in Test 1, there is a mistake in the method for two of the
other tests.

State the two mistakes.

Suggest how each of the mistakes should be corrected.

Mistake 1 __________________________________________________________

Suggestion _________________________________________________________

___________________________________________________________________

Mistake 2 __________________________________________________________

Suggestion _________________________________________________________

___________________________________________________________________
(2)

(c) The missing reagent is added and the mistakes are corrected.

Identify the liquid(s), J, K, L and M, that would react in each test.

State the expected observation for each reaction.

Liquid(s) that react in Test 1 __________________________________________

Expected observation _______________________________________________

__________________________________________________________________

Liquid(s) that react in Test 2 __________________________________________

Expected observation _______________________________________________

__________________________________________________________________

Liquid(s) that react in Test 3 ___________________________________________

Expected observation ________________________________________________

__________________________________________________________________

Liquid(s) that react in Test 4 ___________________________________________

Expected observation ________________________________________________

(8)

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(d) The figure below shows the apparatus that is used to separate a mixture of liquids K and M
using fractional distillation.

Suggest labels that should be added to positions S, T and U in the figure.

Explain why fractional distillation is preferred to simple distillation to separate liquids K and
M.

Label S ____________________________________________________________

Label T ____________________________________________________________

Label U ____________________________________________________________

Explanation ________________________________________________________

___________________________________________________________________
(3)
(Total 14 marks)

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 Endomorphin-2 is a peptide with the amino acid sequence shown.
3.
Tyr–Pro–Phe–Phe–NH2

Each amino acid is represented by a three-letter abbreviation.

Tyr = tyrosine Pro = proline Phe = phenylalanine

Figure 1 shows part of the structure of endomorphin-2, showing the Tyr–Pro–Phe– part of the
molecule.

Figure 1

(a) The –NH2 at the end of the amino acid sequence of endomorphin-2 shows that the terminal
functional group is an amide, not an acid.

Complete the structure of endomorphin-2 in Figure 1.

(2)

(b) Use the structure in Figure 1 to draw the skeletal formula of proline, Pro.

(1)

A student hydrolyses a sample of endomorphin-2 to break it down into its constituent amino
acids.

The student analyses the resulting mixture by thin-layer chromatography, TLC.

(c) State a reagent and the conditions needed for the hydrolysis.

Reagent ___________________________________________________________

Conditions _________________________________________________________
(2)
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(d) Figure 2 shows the apparatus used for the TLC.

Figure 2

There is a piece of the apparatus missing from Figure 2. This omission will result in an
inaccurate chromatogram.

Identify the missing piece of the apparatus.

State and explain why this piece of the apparatus is needed.

Missing piece _______________________________________________________

Explanation ________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)

(e) State why the amino acids separate on the TLC plate.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

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When the solvent has risen up the TLC plate, the student removes the plate from the beaker and
sprays it with a developing agent.

Figure 3 shows the result.

Figure 3

(f) Name a suitable developing agent.

State why the developing agent is needed.

Name _____________________________________________________________

Why needed ________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

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(g) Determine the Rf value for Tyr.

Rf ____________________
(1)
(Total 12 marks)

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 Propanone can be made by reacting propan-2-ol with an excess of acidified potassium
4. dichromate(VI).

The propanone is removed from the reaction mixture by distillation.

(a) The figure below shows the apparatus set up by a student to make propanone by this
method. Suitable clamps are used to hold all the apparatus firmly in place.

There are three problems with the apparatus set up in the figure above.

For each problem:

• identify the problem

• describe the issue it would cause
• suggest how the problem can be solved.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(6)

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Another student completes the experiment using apparatus that is set up correctly.

(b) The student reacts 2.0 cm3 of propan-2-ol (CH3CH(OH)CH3) with an excess of acidified
potassium dichromate(VI).

The student obtains 0.954 g of propanone (CH3COCH3).

Calculate the percentage yield of propanone in this experiment.

Give your answer to the appropriate number of significant figures.

Density of propan-2-ol = 0.786 g cm–3

Percentage yield ____________________

(4)

(c) Molecules of propan-2-ol and propanone each contain three carbon atoms.

Complete the table below to suggest the shape and a bond angle around the central C
atom in a molecule of each compound.

propan-2-ol
Compound propanone CH3COCH3
CH3CH(OH)CH3

Shape around central C

atom

Bond angle around

central C atom

(2)

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 (d) Explain why propanone has a lower boiling point than propan-2-ol.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(3)
(Total 15 marks)

A student plans an experiment to investigate the yield of propanoic acid when a sample of
5. propan-1-ol is oxidised.

The figure below shows the apparatus that the student plans to use for the experiment.

The student’s teacher says that the apparatus is not safe.

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(a) Give two reasons why the apparatus shown in above figure is not safe.

1 _________________________________________________________________

___________________________________________________________________

2 _________________________________________________________________

___________________________________________________________________
(2)

(b) Give one additional reagent that is needed to form any propanoic acid.

___________________________________________________________________
(1)

(c) State two more mistakes in the way the apparatus is set up in above figure.

1 _________________________________________________________________

___________________________________________________________________

2 _________________________________________________________________

___________________________________________________________________
(2)

(d) State the purpose of the small glass beads in the flask in above figure.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

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 (e) After correcting the mistakes, the student heats a reaction mixture containing 6.50 g of
propan-1-ol with an excess of the oxidising agent.
The propanoic acid separated from the reaction mixture has a mass of 3.25 g

State the name of the technique used to separate the propanoic acid from the reaction
mixture.

Calculate the percentage yield of propanoic acid.

Technique __________________________________________________________

Percentage yield _______________

(4)

(f) State a simple chemical test that distinguishes the propanoic acid from the propan-1-ol.

Give one observation for the test with each substance.

Test ______________________________________________________________

Propanoic acid ______________________________________________________

Propan-1-ol _________________________________________________________
(3)
(Total 13 marks)

Aspirin can be produced by reacting salicylic acid with ethanoic anhydride.

6. An incomplete method to determine the yield of aspirin is shown.

1. Add about 6 g of salicylic acid to a weighing boat.

2. Place the weighing boat on a 2 decimal place balance and record the mass.
3. Tip the salicylic acid into a 100 cm3 conical flask.
4. ______________________________________________
5. Add 10 cm3 of ethanoic anhydride to the conical flask and swirl.
6. Add 5 drops of concentrated phosphoric acid.
7. Warm the flask for 20 minutes.
8. Add ice-cold water to the reaction mixture and place the flask in an ice bath.
9. Filter off the crude aspirin from the mixture and leave it to dry.
10. Weigh the crude aspirin and calculate the yield.
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(a) Describe the instruction that is missing from step 4 of the method.

Justify why this step is necessary.

Instruction ________________________________________________________

Justification _______________________________________________________

__________________________________________________________________

__________________________________________________________________
(2)

(b) Suggest a suitable piece of apparatus to measure out the ethanoic anhydride in step 5.

___________________________________________________________________
(1)

(c) Identify a hazard of using concentrated phosphoric acid in step 6.

___________________________________________________________________
(1)

(d) Complete the equation for the reaction of salicylic acid with ethanoic anhydride to produce
aspirin.

(1)

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(e) A 6.01 g sample of salicylic acid (Mr = 138.0) is reacted with
10.5 cm3 of ethanoic anhydride (Mr = 102.0).
In the reaction the yield of aspirin is 84.1%

The density of ethanoic anhydride is 1.08 g cm–3

Show by calculation which reagent is in excess.

Calculate the mass, in g, of aspirin (Mr = 180.0) produced.

Reagent in excess _______________

Mass of aspirin __________ g

(5)

(f) Suggest two ways in which the melting point of the crude aspirin collected in step 9 would
differ from the melting point of pure aspirin.

Difference 1 _________________________________________________________

___________________________________________________________________

Difference 2 _________________________________________________________

___________________________________________________________________
(2)

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 (g) The crude aspirin can be purified by recrystallisation using hot ethanol
(boiling point = 78 °C) as the solvent.

Describe two important precautions when heating the mixture of ethanol and crude aspirin.

Precaution 1 ________________________________________________________

___________________________________________________________________

Precaution 2 ________________________________________________________

___________________________________________________________________
(2)

(h) The pure aspirin is filtered under reduced pressure.

A small amount of cold ethanol is then poured through the Buchner funnel.

Explain the purpose of adding a small amount of cold ethanol.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(i) A sample of the crude aspirin is kept to compare with the purified aspirin.

Describe one difference in appearance you would expect to see between these two solid
samples.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 16 marks)

Cyclohexene (boiling point = 83 °C) can be prepared by the dehydration of cyclohexanol (boiling
7. point = 161 °C) using concentrated phosphoric acid.

A student prepared cyclohexene by placing 10 cm3 of cyclohexanol (density = 0.96 g cm–3) into a
round-bottomed flask.

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3 cm3 of concentrated phosphoric acid were then carefully added to the flask.
The student added a few anti-bumping granules and set up the apparatus shown in the diagram.

• The student heated the mixture and collected the liquid that distilled at temperatures below
100 °C
• The distillate was poured into a separating funnel and washed by shaking with sodium
carbonate solution.
• Periodically, the separating funnel was inverted and the tap opened.
• The aqueous layer was discarded and the final organic product was dried using anhydrous
calcium chloride.
• After the product was dried, the drying agent was removed by filtration under reduced
pressure.

(a) The student collected 5.97 g of cyclohexene in the experiment.

Calculate the percentage yield of cyclohexene.

Percentage yield ____________________ %

(3)

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(b) Describe a test-tube reaction, on the product, to show that the cyclohexanol had been
dehydrated.

State what you would observe. __________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(c) Suggest why sodium carbonate solution was used to wash the distillate.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(d) Explain why it is important to open the tap of the separating funnel periodically.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e) Give a property of anhydrous calcium chloride, other than its ability to absorb water, that
makes it suitable as a drying agent in this preparation.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

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(f) Describe the apparatus used to remove the drying agent by filtration under reduced
pressure. Your description of the apparatus can be either a labelled diagram or a
description in words.

(2)

(g) A sample of cyclohexene has been contaminated with cyclohexanol. The cyclohexene can
be separated from the cyclohexanol by column chromatography.
Silica gel is used as the stationary phase and hexane as the mobile phase.

Explain why cyclohexene has a shorter retention time than cyclohexanol.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(2)

(h) Explain how an infrared spectrum would confirm that the cyclohexene obtained from the
chromatography column did not contain any cyclohexanol.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)
(Total 13 marks)

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 Propane-1,2-diol has the structure CH2(OH)CH(OH)CH3. It is used to make polyesters and is one
8. of the main substances in electronic cigarettes (E-cigarettes).

A sample of propane-1,2-diol was refluxed with a large excess of potassium dichromate(VI) and
sulfuric acid.

(a) Draw the skeletal formula of propane-1,2-diol.

(1)

(b) Write an equation for this oxidation reaction of propane-1,2-diol under reflux, using [O] to
represent the oxidizing agent.

Show the displayed formula of the organic product.

___________________________________________________________________
(2)

(c) Draw a labelled diagram to show how you would set up apparatus for refluxing.

(2)

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(d) Anti-bumping granules are placed in the flask when refluxing.
Suggest why these granules prevent bumping.

___________________________________________________________________

___________________________________________________________________

___________________________________________________________________
(1)

(e) Draw the structure of a different organic product formed when the acidified potassium
dichromate(VI) is not in excess.

(1)
(Total 7 marks)

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