Organic Analysis QP

AQA Chemistry A-Level - Organic Analysis QP PhysicsAndMathsTutor.
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Q1.
This question is about spectroscopy.
(a) Compound K has molecular formula C4H8O

Figure 1 shows the infrared spectrum of K.
Figure 1
Which functional group does K contain?
Tick (✓) one box.
Functional Group
alcohol alkene amine carbonyl nitrile
(1)
(b) Compound L has molecular formula C4H7NO

Figure 2 shows the infrared spectrum of L.
Figure 2
Page 1 of 22
AQA Chemistry A-Level - Organic Analysis QP PhysicsAndMathsTutor.com
L reacts with H2 in the presence of a nickel catalyst to give compound M.
Suggest three ways in which the infrared spectrum of M is different from

the infrared spectrum of L.
1 _________________________________________________________
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2 _________________________________________________________
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3 _________________________________________________________
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(3)
(c) Figure 3 shows the 1H NMR spectrum of Q, C3H7ClO
Figure 3
The table below shows the chemical shifts (δ values) and integration
values for each peak.
δ value / ppm 3.95 3.65 3.35
Integration
0.6 0.6 0.9
value
Deduce the structure of Q.
Explain your answer.
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Page 2 of 22
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(5)
(Total 9 marks)
Q2.
Which statement does not support the suggestion that an unknown organic
compound is
A Its 1H NMR spectrum has 3 peaks with an integration

ratio of 2:3:3
B Its 13C NMR spectrum has 3 peaks.
C Its infrared spectrum has an absorption at 1735 cm−1
D It has 36.36% by mass of oxygen and 9.09% by mass

of hydrogen.
(Total 1 mark)
Q3.
This question is about the structural isomers shown.
Page 3 of 22
(a) Identify the isomer(s) that would react when warmed with acidified
potassium dichromate(VI).
State the expected observation when acidified potassium dichromate(VI)

reacts.
Isomer(s)
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Expected observation
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(2)
(b) Identify the isomer(s) that would react with Tollens’ reagent.
State the expected observation when Tollens’ reagent reacts.
Isomer(s)
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Expected observation
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(2)
(c) Separate samples of each isomer are warmed with ethanoic acid and a few
drops of concentrated sulfuric acid. In each case the mixture is then poured
into a solution of sodium hydrogencarbonate.
Identify the isomer(s) that would react with ethanoic acid.
Suggest a simple way to detect if the ethanoic acid reacts with each
isomer.
Give a reason why the mixture is poured into sodium hydrogencarbonate

solution.
Isomer(s)
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Suggestion
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Reason
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(3)
Page 4 of 22
(d) State the type of structural isomerism shown by isomers P, Q, R and S.
___________________________________________________________
(1)
(e) Describe fully how infrared spectra can be used to distinguish between
isomers R, S and T.
Use data from Table A in the Data Booklet in your answer.
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(4)
(f) State why mass spectrometry using electrospray ionisation is not a

suitable method to distinguish between the isomers.
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(1)
(Total 13 marks)
Q4.
The structures of three organic compounds A, B and C are shown.
These compounds can be distinguished by simple test-tube reactions.
For each pair of compounds in questions (a) and (b), give a reagent (or
combination of reagents) that could be added separately to each compound to
distinguish between them.
State what is observed in each case.
Page 5 of 22
(a) Compounds A and B
Reagent
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Observation with A __________________________________________
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Observation with B __________________________________________
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(3)
(b) Compounds A and C
Reagent
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Observation with A __________________________________________
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Observation with C __________________________________________
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(3)
(Total 6 marks)
Page 6 of 22
Q5.
The infrared spectrum of an organic compound is shown.
Which compound produces this spectrum?
A ethanoic acid
B 4-hydroxybutanone
C propan-1-ol
D prop-2-en-1-ol
(Total 1 mark)
Q6.
This question is about isomers.
(a) Give a reagent and observations for a test-tube reaction to distinguish

between 2-methylbutan-1-ol and 2-methylbutan-2-ol.
Reagent
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Observation with 2-methylbutan-1-ol ____________________________
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Page 7 of 22
Observation with 2-methylbutan-2-ol ____________________________
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(3)
(b) Compounds A and B both have the molecular formula C4H8Br2

A has a singlet, a triplet and a quartet in its 1H NMR spectrum.
B has only two singlets in its 1H NMR spectrum.
Draw a structure for each of A and B.
A B
(2)
(c) Compounds C and D both have the molecular formula C6H3Br3

C has two peaks in its 13C NMR spectrum.
D has four peaks in its 13C NMR spectrum.
Draw a structure for each of C and D
C D
Page 8 of 22
(2)
(d) Compounds E, F, and G are isomers.
The diagrams below show the infrared spectra of these isomers, but not
necessarily in the same order.
Label each spectrum with the correct letter E, F, and G in the box.
(1)
(Total 8 marks)
Page 9 of 22
Q7.
Isomers X and Y have the molecular formula C5H8O
(a) Give the IUPAC name for isomer X.
___________________________________________________________
(1)
(b) Explain how and why isomers X and Y can be distinguished by comparing
each of their
• boiling points
• 13C NMR spectra
• infrared spectra.
Use data from Tables A and C in the Data Booklet in your answer.
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(6)
(Total 7 marks)
Page 10 of 22
Q8.
Three reagents are added separately to four organic compounds.
Which row shows the correct observations?
Sodium Acidified
Tollens’
hydrogen potassium
reagent
carbonate dichromate(VI)
orange solution no visible

A Propan-1-ol effervescence
turns green change
orange solution
B Propanal no visible change silver mirror
turns green
C Propanone no visible change no visible change silver mirror
Propanoic
D effervescence no visible change silver mirror
acid
(Total 1 mark)
Q9.
Four compounds, all colourless liquids, are
• butan-2-ol
• butanal
• butanone
• 2-methylpropan-2-ol
Two of these compounds can be identified using different test-tube reactions.
Describe these two test-tube reactions by giving reagents and observations in

each case.
Suggest how the results of a spectroscopic technique could be used to
distinguish between the other two compounds.
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Page 11 of 22
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(Total 6 marks)
Q10.
The infrared spectrum of an organic compound is shown.
Which compound produces this spectrum?
A butanone
B ethanol
C pent-2-ene
D propanoic acid
(Total 1 mark)
Page 12 of 22
Q11.
Which compound forms a molecular ion with a different precise molecular mass
from the other three?
A butanone
B cyclobutanol
C dimethylpropane
D methylpropanal
(Total 1 mark)
Q12.
Test-tube reactions can be used to identify the functional groups in organic
molecules.
You are provided with samples of each of the four compounds.
Describe how you could distinguish between all four compounds using the
minimum number of tests on each compound.
You should describe what would be observed in each test.
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(Total 6 marks)
Page 13 of 22
Q13.
Which compound gives this infrared spectrum?
A 1-bromobutane
B butan-1-ol
C butanal
D butanoic acid
(Total 1 mark)
Q14.
Which of these infrared spectra could represent a carboxylic acid?
Page 14 of 22
(Total 1 mark)
Page 15 of 22
Q15.
1H NMR, 13C NMR and infrared spectroscopy are used in organic chemistry to
distinguish between compounds and to identify them.
(a) Give the skeletal formula of the compound that is used as the standard
when recording a 13C NMR spectrum.
(1)
(b) Four isomers of C6H12O2, P, Q, R and S, shown in Figure 1, were analysed

by
13C NMR spectrometry.
The 13C NMR spectra of three of these isomers are shown in Figure 2.
Page 16 of 22
Use Table C in the Data Booklet to help you to identify which isomer
produces each spectrum.
Write the letter of each isomer opposite its spectrum in Figure 2.
Figure 2
Page 17 of 22
(3)
(c) The infrared spectra shown in Figure 3 are those of three different isomers
of C6H12O2, isomers T, U and V.
Page 18 of 22
Identify the functional group(s) present in each isomer T, U and V of

C6H12O2 using Table A in the Data Booklet.
Explain your answer.
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Page 19 of 22
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(6)
(d) The integration values for the peaks in the 1H NMR spectrum of X, a
different isomer of C6H12O2, are given in the table below.
Chemical shift, δ/ppm 3.7 3.5 2.6 2.2 1.1
Integration value 0.6 0.6 0.6 0.9 0.9
Splitting pattern triplet quartet triplet singlet triplet
Deduce the simplest ratio of the relative numbers of protons in each

environment in compound X.
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(1)
(e) Use the data in the table above and Table B in the Data Booklet to help
you answer this question.
Deduce the part of the structure of X that causes the signal at δ= 3.5 and
the part of the structure at X that causes the signal at δ=2.2.
Explain the splitting patterns of these peaks.
Signal at δ= 3.5
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Signal at δ= 2.2
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(4)
Page 20 of 22
(f) Deduce the structure of compound X, C6H12O2
Use your answer from part (e) to help you.
You are not required to explain how you deduced the structure.
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(2)
(Total 17 marks)
Q16.
The infrared spectrum (Figure 1) and the 1H NMR spectrum (Figure 2) of
compound R with molecular formula C6H14O are shown.
Figure 1
Figure 2
Page 21 of 22
The relative integration values for the NMR peaks are shown on Figure 2.
Deduce the structure of compound R by analysing Figure 1 and Figure 2.

Explain each stage in your deductions.
Use Table A and Table B on the Data Sheet.
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(Total 8 marks)
Page 22 of 22

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AQA Chemistry A-Level - Organic Analysis QP PhysicsAndMathsTutor.

(a) Compound K has molecular formula C4H8O

Which functional group does K contain?

Tick (✓) one box.

alcohol alkene amine carbonyl nitrile

(b) Compound L has molecular formula C4H7NO

L reacts with H2 in the presence of a nickel catalyst to give compound M.

Suggest three ways in which the infrared spectrum of M is different from

(c) Figure 3 shows the 1H NMR spectrum of Q, C3H7ClO

δ value / ppm 3.95 3.65 3.35

Deduce the structure of Q.

Explain your answer.

A Its 1H NMR spectrum has 3 peaks with an integration

B Its 13C NMR spectrum has 3 peaks.

C Its infrared spectrum has an absorption at 1735 cm−1

D It has 36.36% by mass of oxygen and 9.09% by mass

State the expected observation when acidified potassium dichromate(VI)

State the expected observation when Tollens’ reagent reacts.

Identify the isomer(s) that would react with ethanoic acid.

Give a reason why the mixture is poured into sodium hydrogencarbonate

(d) State the type of structural isomerism shown by isomers P, Q, R and S.

(f) State why mass spectrometry using electrospray ionisation is not a

These compounds can be distinguished by simple test-tube reactions.

State what is observed in each case.

(a) Compounds A and B

Observation with A __________________________________________

Observation with B __________________________________________

(b) Compounds A and C

Observation with A __________________________________________

Observation with C __________________________________________

Which compound produces this spectrum?

(a) Give a reagent and observations for a test-tube reaction to distinguish

Observation with 2-methylbutan-1-ol ____________________________

Observation with 2-methylbutan-2-ol ____________________________

(b) Compounds A and B both have the molecular formula C4H8Br2

Draw a structure for each of A and B.

(c) Compounds C and D both have the molecular formula C6H3Br3

Draw a structure for each of C and D

(d) Compounds E, F, and G are isomers.

(a) Give the IUPAC name for isomer X.

• 13C NMR spectra

Which row shows the correct observations?

orange solution no visible

C Propanone no visible change no visible change silver mirror

Two of these compounds can be identified using different test-tube reactions.

Describe these two test-tube reactions by giving reagents and observations in

Which compound produces this spectrum?

You are provided with samples of each of the four compounds.

You should describe what would be observed in each test.

(b) Four isomers of C6H12O2, P, Q, R and S, shown in Figure 1, were analysed

Write the letter of each isomer opposite its spectrum in Figure 2.

Identify the functional group(s) present in each isomer T, U and V of

Explain your answer.

Chemical shift, δ/ppm 3.7 3.5 2.6 2.2 1.1

Integration value 0.6 0.6 0.6 0.9 0.9

Splitting pattern triplet quartet triplet singlet triplet

Deduce the simplest ratio of the relative numbers of protons in each

Explain the splitting patterns of these peaks.

(f) Deduce the structure of compound X, C6H12O2

Use your answer from part (e) to help you.