Infrared (IR) Spectroscopy_124006

Edexcel Chemistry A-level - Infrared (IR) Spectroscopy PhysicsAndMathsTutor.
com
Questions
Q1.
The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of

concentrated hydrochloric acid with 2-methylpropan-2-ol, (CH3)3COH, a tertiary alcohol.
(CH3)3COH + HCl → (CH3)3CCl + H2O
In an experiment, 12.0 g of 2-methylpropan-2-ol was shaken with excess concentrated

hydrochloric acid in a separating funnel.
After about 15 minutes, the product formed as a separate layer.
Data:
The dried 2-chloro-2-methylpropane was transferred to the distillation apparatus.
11.6 cm3 of 2-chloro-2-methylpropane was collected from 12.0 g of 2-methylpropan-2-ol.
Infrared spectroscopy can be used to determine the purity of a substance.
(i) State how infrared spectroscopy could be used to show that no 2-methylpropan-2-ol was
present in the distillate.
(1)
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(ii) Give one advantage and one disadvantage of using a chemical test rather than infrared
spectroscopy to determine whether any of the 2-methylpropan-2-ol remained.
(2)
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(Total for question = 3 marks)
Edexcel Chemistry A-level - Infrared (IR) Spectroscopy PhysicsAndMathsTutor.com
Q2.
This question is about the preparation of a sample of the ketone, 3-methylbutan-2-one.
A student's research suggested that 3-methylbutan-2-one may be prepared by oxidising

3-methylbutan-2-ol with acidified potassium dichromate(VI) solution.
The student sets up the apparatus as shown in the diagram. You may assume that all the
equipment is suitably clamped.
The student adds dilute sulfuric acid to the pear-shaped flask. A mixture of potassium
dichromate(VI) and 3-methylbutan-2-ol is then added slowly to the dilute sulfuric acid in the
flask.
The organic mixture was separated from the aqueous layer and dried.
The infrared spectrum of the organic mixture is shown.
(i) By reference to any relevant peak(s), deduce how the infrared spectrum shows that the
mixture contains 3-methylbutan-2-one.
(2)
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(ii) From the infrared spectrum, the student concludes that the mixture contains another
organic compound.
The mixture is redistilled and the fraction that boils in the range 93–95°C is collected. The
boiling temperature of 3-methylbutan-2-one is 94°C.
Predict any change(s) you would see in the infrared spectrum after redistillation, justifying
your answer.
(2)
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Q3.
This question is about some reactions of cyclohexanol.
(i) Give the name and displayed formula of compound B.

(2)
(ii) The infrared (IR) spectra of cyclohexanol and compound B are shown.
Identify the bonds, using both IR spectra, that help to confirm the reaction of
cyclohexanol to produce compound B.
Your answer must include the wavenumber ranges of any relevant bonds.
(2)
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(iii) The mass spectrum of compound B is shown.
Deduce the relative molecular mass of compound B using the mass spectrum. Justify
your answer.
(1)
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(iv) In the mass spectrum of cyclohexanol, there is a peak at m/z = 83.

Give the formula of a fragment that could be responsible for this peak.
(2)

Q4.
Analysis shows that a compound has the molecular formula C4H8O2.
A student suggests that the compound could be either A or B.
Another student suggests that the compound could contain an aldehyde and an alcohol
functional group, with structure C.
Complete the table to show how the infrared spectra of A, B and C would be expected to
differ in the wavenumber range 1800-1600 cm−1.
Use information from the Data Booklet.
(3)

Q5.
* This question is about compounds with the molecular formula C4H8O.

Three different compounds, A, B and C, have the molecular formula C4H8O.
Information about these three compounds includes:
• all three compounds have infrared absorptions at about 3500 cm–1

• the infrared spectra of A and B each contain a peak at about 1650 cm–1, while that of C
does not
• only A has a branched carbon chain
• B is the E-isomer of a pair of stereoisomers.
Deduce a possible displayed formula for each of the compounds A, B and C.
You must use all the information and the Data Booklet to fully justify each of your structures.
(6)
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Q6.
Organic compounds containing nitrogen include amides, amines, amino acids and nitriles.
A compound produced a peak due to an N—H stretching vibration in its infrared spectrum
with
a wavenumber of 3220 cm–1.
This compound could be

(1)
A an amide
B an amine
C either an amide or an amine
D neither an amide nor an amine
(Total for question = 1 mark)

Q7.
This is a question about the analysis of three aromatic substances with —OH groups.
Spectroscopy is an effective means of distinguishing between molecules.
(i) Compare and contrast the infrared spectra of phenol, phenylmethanol and benzoic acid.
Include relevant bonds and their wavenumber ranges using the Data Booklet.
(5)
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(ii) Predict the number of peaks present, and their chemical shifts, in the 13C nuclear
magnetic resonance (NMR) spectrum of
phenylmethanol.
Use the information in the Data Booklet to help you.
(3)
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(iii) Give the formula of a fragment ion, with its m/z value, that you would expect to be
present in the mass spectrum of
benzoic acid but not in the mass spectrum of phenol or the mass spectrum of
phenylmethanol.
(2)
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Q8.
(a) The infrared spectrum of geraniol is shown.
Using the table of absorptions from the Data Booklet and the infrared spectrum, give the
names of the two functional groups present in geraniol.To confirm these functional groups,
give the wavenumber ranges and their corresponding bonds.
(2)
First functional group
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Second functional group
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(b) Give one chemical test that you could use to confirm the presence of each of the two
functional groups suggested in part (a). Predict a result for each test.
(4)
Test and result for first functional group
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Test and result for second functional group
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Q9.
(a) This question is about the analysis of an unknown carboxylic acid X by three students.
The students analyse the mass spectrum of X and find that it has a molecular ion peak at
m / z = 116.
The three students each propose a different structural formula for compound X.
Structure 1 HOOCCH==CHCOOH
Structure 2 HOCH2CH==CHCH2COOH
Structure 3 CH3CH2CH2CH2CH2COOH
The students are given the infrared spectrum of X.
(i) State two wavenumber ranges of the infrared absorptions providing evidence that
compound X is a carboxylic acid. Include the bonds responsible.
(2)
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(ii) One of the students suggests that this infrared spectrum and the data in the Data
Booklet alone could be used to identify which of the three proposed structures is X.
Show that this student's suggestion is correct. Include relevant infrared data in your
answer.
(3)
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(b) The students decide to carry out an acid-base titration to obtain further information about
compound X.
Each student uses solid sodium hydroxide, NaOH, to prepare a solution of concentration
0.140 mol dm−3.
Calculate the mass, in grams, of solid sodium hydroxide that each student should weigh
out to prepare 250.0 cm3 of a 0.140 mol dm−3 solution.
(2)
(c) Each of the students makes up 250.0 cm3 of 0.140 mol dm−3 sodium hydroxide solution
in a volumetric flask and titrates this solution with the same solution of X of known
concentration.
Student A
• correctly prepares the 0.140 mol dm−3 sodium hydroxide solution and pipettes a volume
of 10.0 cm3 of the solution into a conical flask
• fills a burette with the solution of X and carries out a titration
• repeats the procedure until obtaining concordant results
• obtains a mean titre of 10.20 cm3.
Student B
• dissolves the sodium hydroxide in distilled water and transfers the solution to a
volumetric flask
• adds more distilled water to the volumetric flask and mixes the solution
• notices that the volumetric flask has been filled with distilled water several cm3 beyond
the graduation mark
• realises the mistake, removes the extra solution and discards it
• pipettes 10.0 cm3 of the sodium hydroxide solution into a conical flask and titrates this
with the solution of X.
Student C
• correctly prepares the 0.140 mol dm−3 sodium hydroxide solution

• washes a conical flask thoroughly with distilled water and pipettes 10.0 cm3 of the
sodium hydroxide solution into the wet conical flask
• titrates the contents of the conical flask with the solution of X.
(i) Explain how, if at all, Student B's mistake affects the value of the titre.
(2)
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(ii) Explain how, if at all, Student C's use of a wet conical flask affects the value of the
titre.
(2)
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(iii) Student A uses three pieces of apparatus to measure volumes in this experiment.
• The burette has an uncertainty of ±0.05 cm3 for each volume reading
• The volumetric flask has an uncertainty of ±0.30 cm3 for the volume
• The pipette has an uncertainty of ±0.04 cm3 for the volume
Show by calculation which volume measurement has the lowest percentage
uncertainty.
(3)
(d) Student A calculates the correct value for the molar mass of compound X, using the
mean titre of 10.20 cm3. The results indicate that X has structure 1.
Structure 1 HOOCCH==CHCOOH
Structure 2 HOCH2CH==CHCH2COOH
Structure 3 CH3CH2CH2CH2CH2COOH
(i) Write the equation for the reaction between structure 1 and sodium hydroxide
solution. State symbols are not required.
(2)
(ii) Deduce the value that would have been obtained for the mean titre if the structural
formula of X had been structure 2.
Justify your answer.
(2)
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(e) The students could have identified the three structures using chemical tests.
Complete the table to show whether or not the suggested structures react with bromine
water and when heated with acidified potassium dichromate(VI).
Use a tick ( ) if a reaction occurs.
Use a cross ( ) if no reaction occurs.
(2)
(f) The structure HOOCCH==CHCOOH has two stereoisomers.

(i) Draw the structures of these stereoisomers.
(2)
E-isomer
Z-isomer
(ii) State why HOOCCH==CHCOOH has E/Z isomers.

(2)
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Mark Scheme
Q1.
Q2.
Q3.
Q4.
Q5.
Q6.
Q7.
Q8.
Q9.

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Edexcel Chemistry A-level - Infrared (IR) Spectroscopy PhysicsAndMathsTutor.

The preparation of 2-chloro-2-methylpropane, (CH3)3CCl, involves the reaction of

(CH3)3COH + HCl → (CH3)3CCl + H2O

In an experiment, 12.0 g of 2-methylpropan-2-ol was shaken with excess concentrated

After about 15 minutes, the product formed as a separate layer.

The dried 2-chloro-2-methylpropane was transferred to the distillation apparatus.

11.6 cm3 of 2-chloro-2-methylpropane was collected from 12.0 g of 2-methylpropan-2-ol.

Infrared spectroscopy can be used to determine the purity of a substance.

This question is about the preparation of a sample of the ketone, 3-methylbutan-2-one.

A student's research suggested that 3-methylbutan-2-one may be prepared by oxidising

The infrared spectrum of the organic mixture is shown.

(Total for question = 4 marks)

This question is about some reactions of cyclohexanol.

(i) Give the name and displayed formula of compound B.

(iii) The mass spectrum of compound B is shown.

(iv) In the mass spectrum of cyclohexanol, there is a peak at m/z = 83.

(Total for question = 7 marks)

Analysis shows that a compound has the molecular formula C4H8O2.

A student suggests that the compound could be either A or B.

(Total for question = 3 marks)

* This question is about compounds with the molecular formula C4H8O.

• all three compounds have infrared absorptions at about 3500 cm–1

This compound could be

(Total for question = 1 mark)

Spectroscopy is an effective means of distinguishing between molecules.

(Total for question = 10 marks)

(a) The infrared spectrum of geraniol is shown.

Second functional group

Test and result for second functional group

(Total for question = 6 marks)

• correctly prepares the 0.140 mol dm−3 sodium hydroxide solution

(f) The structure HOOCCH==CHCOOH has two stereoisomers.

(ii) State why HOOCCH==CHCOOH has E/Z isomers.

(Total for question = 24 marks)

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