Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

Modern Chemical Analysis_Worksheet_1

Section A
1 When propanal, CH3CH2CHO, and propanone, CH3COCH3, are compared
using physical methods of analysis, which of the following is not correct?

2 Under certain conditions, butan-1-ol can be oxidized to the compound with

infrared spectrum shown below.

The compound is most likely to be

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

3 Which of the following molecules does not absorb infrared radiation?

4 There would be a major peak in the mass spectrum for butan-1-ol,

CH3CH2CH2CH2OH, but not for butan-2-ol, CH3CH2CH(OH)CH3, at m/e value

5 How many molecular ion peaks (parent ion peaks) occur in the mass
spectrum of 1,2-dibromoethane, CH2BrCH2Br?
Assume the only isotopes present are 1H, 12C, 79Br and 81Br.

6 These questions concern the use of infrared (IR) spectra to identify organic
compounds.
The IR absorption ranges associated with some organic functional groups are
given below.

(a) When propan-2-ol is refluxed with potassium dichromate(VI) and sulfuric

acid, the product will show a peak due to

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

(b) When propan-1-ol is heated with potassium dichromate(VI) and sulfuric

acid, the product, that is distilled off as it is formed, will show a peak due to

7 The molecular (parent) ion in the mass spectrum of a hydrocarbon

containing 12C and 1H only

8 A compound which has major peaks with mass / charge ratio at 29, 57 and
58 in the mass spectrum could be

9 Which type of radiation is absorbed by molecules and results in the

greenhouse effect?

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

10 Consider the infrared spectrum shown below.

The IR absorption ranges associated with some organic functional groups are
given below.

Which of the following could have produced the above spectrum?

11 In a mass spectrum of butane, C4H10, where would a peak be seen for the
molecular ion if it had a charge of 2+?

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

12 This question is about two isomeric alcohols and two isomeric carbonyl
compounds.
Butan-1-ol, CH3CH2CH2CH2OH
Butan-2-ol, CH3CH2CH(OH)CH3
Butanal, CH3CH2CH2CHO
Butanone, CH3CH2COCH3
(d) The infrared spectrum of one of these compounds is given below.

Use the infrared absorptions, in wavenumbers, to identify the compound.

The compound with this IR spectrum is

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

13 What effect does infrared radiation have on the covalent bonds in water
molecules in the atmosphere?

14 The fragment with a peak of m/e = 43 is present in the mass spectrum of

15 Depending on the conditions, ethanol, CH3CH2OH, can be oxidized to

ethanal, CH3CHO, ethanoic acid, CH3COOH or mixture of the two.
Mass spectrometry can be used to identify the products.
The absence of a fragment ion peak m/e = 45 indicates that

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

16 The mass spectrum of propan‑1‑ol is shown.

Which peak represents the molecular ion for propan‑1‑ol containing a carbon‑13
isotope?

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

Section B
2 Consider the following reaction scheme.

The infrared spectrum of compound S is shown below.

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

(a) (i) Give the wavenumber range of the absorption in the infrared spectrum
that shows that compound S is an alcohol.
(1)
............................................................................................................................
(ii) Identify the type of organic compound formed in the reaction of S with
phosphorus(V) chloride, PCl5.
(1)
............................................................................................................................
(b) Compound T does not produce carbon dioxide when added to a solution of
sodium carbonate.
From this information alone, what can you deduce about compound T?
(1)
............................................................................................................................
(c) The infrared spectrum of liquid T is shown below.

(i) Give the wavenumber range of the absorption in the infrared spectrum that
shows that compound T is formed from a secondary alcohol.
(1)
............................................................................................................................
(ii) Identify the type of organic compound T.
(1)
............................................................................................................................
(iii) Draw the skeletal formula for S.
(1)

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

(d) Liquid X gives a white precipitate, R, on warming with an aqueous

ethanolic solution of silver nitrate.
(i) Identify R by name or formula.
(1)
............................................................................................................................
(ii) Describe what you would see if precipitate R was left in sunlight.
(1)
............................................................................................................................
............................................................................................................................
(iii) Suggest why an aqueous ethanolic solution of silver nitrate gives a better
result in this test than would be obtained by aqueous silver nitrate.
(1)
............................................................................................................................
............................................................................................................................
............................................................................................................................
(e) If X is heated with a concentrated ethanolic solution of potassium
hydroxide, a gas Q is produced.
(i) Describe a test and its expected result to show that this gas is an alkene.
(2)
Test ....................................................................................................................
............................................................................................................................
Result .................................................................................................................
............................................................................................................................
(ii) Give the displayed formula of the alkene Q.
(1)

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

Q2.
(a) (i) Depending on the reaction conditions, ethanol can be oxidized to either
an aldehyde or to carboxylic acid. Infrared spectroscopy is a suitable
technique for determining whether the oxidation product obtained is an
aldehyde or a carboxylic acid.
Draw, on the spectrum below, any peak(s) that you would expect to see
between 4000 and 1500 cm–1 if the product was an aldehyde and not a
carboxylic acid.
(2)

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Edexcel Chemistry IAS Modern Chemical Analysis_Worksheet_1

(ii) The infrared spectrum of the distillate from the reaction in (e)(i) included a
peak at 3750–3200 cm–1.
What substance is likely to have caused this?
(1)
............................................................................................................................
(iii) Mass spectrometry can be used to identify the products of the oxidation of
ethanol. Suggest the formula of a fragment that would show when ethanoic
acid is produced and would not be present in either ethanol or ethanal.
(1)
............................................................................................................................

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