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1. The H NMR spectrum of X with molecular formula C3H6O is shown below.

(a) Deduce which of the following compounds is X and explain your answer.

CH3–CO–CH3 CH3–CH2–CHO CH2=CH–CH2OH

Compound:

......................................................................................................................................

Explanation:

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

IB Questionbank Chemistry 1
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(b) Deduce which one of the peaks in the H NMR spectrum of X would also occur in the
spectrum of one of the other isomers, giving your reasoning.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

(c) The infrared and mass spectra for X were also recorded.

(i) Apart from absorptions due to C–C and C–H bonds, suggest one absorption, in
wavenumbers, that would be present in the infrared spectrum.

...........................................................................................................................
(1)

(ii) Apart from absorptions due to C–C and C–H bonds, suggest one absorption, in
wavenumbers, absent in this infrared spectrum but present in one of the other
compounds shown in part (a).

...........................................................................................................................
(1)

(d) Suggest the formulas and m/z values of two species that would be detected in the mass
spectrum.

Species: .......................................................................................................................

m/z: .............................................................................................................................

Species: .......................................................................................................................

m/z: .............................................................................................................................
(2)
(Total 8 marks)

IB Questionbank Chemistry 2
2. Selected regions of the electromagnetic spectrum are represented in order of increasing
frequency below.

(a) Identify region A.

......................................................................................................................................
(1)

(b) Identify the atomic or molecular processes associated with microwave and ultraviolet
radiation.

Microwave:

......................................................................................................................................

Ultraviolet:

......................................................................................................................................
(2)

(c) State which region of the electromagnetic spectrum can be used to identify the functional
groups present in a molecule.

......................................................................................................................................
(1)

IB Questionbank Chemistry 3
 (d) Explain why the absorptions in infrared (IR) spectroscopy occur at much higher
1
frequency than those in H NMR spectroscopy.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)
(Total 6 marks)

3. Infrared spectroscopy is commonly used as an analytical technique by inorganic, physical and

organic chemists.

(a) Explain why hydrogen bromide is IR active whereas bromine is IR inactive.

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(1)

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(b) The IR spectrum, mass spectrum and H NMR spectrum of an unknown compound, X, of
molecular formula C5H10O2, are as follows.

IB Questionbank Chemistry 4
 [Source: SDBSWeb:http://riod01.ibase.aist.go.jp/sdbs/(National Institute of Advanced Industrial Science and
Technology)]

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 (i) In the IR spectrum, identify the bond responsible for each of the absorptions
labelled I, II and III.

I: ......................................................................................................................

II: .....................................................................................................................

III: ....................................................................................................................
(3)

(ii) In the mass spectrum, deduce which fragments the m/z values at 102, 57 and 45
correspond to.

m/z = 102: .........................................................................................................

m/z = 57: ...........................................................................................................

m/z = 45: ...........................................................................................................

(3)

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(iii) Identify the peak at 11.5 ppm in the H NMR spectrum.

...........................................................................................................................
(1)

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(iv) State what information can be obtained from the integration traces in the H NMR
spectrum about the hydrogen atoms responsible for the peak at 1.2 ppm.

...........................................................................................................................

...........................................................................................................................
(1)

IB Questionbank Chemistry 6
 (v) Deduce the structure of X.

(1)

(vi) CH3COOCH2CH2CH3 is an isomer of X. Deduce two differences between the

1
H NMR spectrum of this isomer and that of X.

...........................................................................................................................

...........................................................................................................................

...........................................................................................................................

...........................................................................................................................
(2)
(Total 12 marks)

IB Questionbank Chemistry 7
 1
4. The IR spectrum, mass spectrum and H NMR spectrum of an unknown compound, X, of
molecular formula C3H6O2 are as follows.

[Source: SDBSWeb: http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and

Technology)]

IB Questionbank Chemistry 8
 (i) Identify the bonds responsible for the peaks A, B and C in the IR spectrum of X.

A: .................................................................................................................................

B: .................................................................................................................................

C: .................................................................................................................................
(2)

(ii) In the mass spectrum of X, deduce which ions the m/z values at 74, 45 and 29 correspond
to.

m/z = 74: ......................................................................................................................

m/z = 45: ......................................................................................................................

m/z = 29: ......................................................................................................................

(3)

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(iii) Identify the peak at 11.73 ppm in the H NMR spectrum.

......................................................................................................................................
(1)

(iv) Deduce the structure of X.

(1)
(Total 7 marks)

IB Questionbank Chemistry 9
5. Explain what occurs at a molecular level during the absorption of infrared (IR) radiation by the
sulfur dioxide molecule, SO2.

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................
(Total 3 marks)

6. Consider the IR spectra of the following three compounds.

A = CH3(CH2)3COOH

B = CH3COOC(CH3)3

C = (CH3CH2)3COH

IB Questionbank Chemistry 10
 Determine which IR spectrum corresponds to each compound A, B and C. Explain your
reasoning. IR data can be found in Table 17 of the Data Booklet.

Compound Spectrum Reason

.............................................................................................
A ........... .............................................................................................

.............................................................................................

.............................................................................................
B ........... .............................................................................................

.............................................................................................

.............................................................................................
C ........... .............................................................................................

.............................................................................................
(Total 5 marks)

IB Questionbank Chemistry 11
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7. A feature of some H NMR spectra is the electron-withdrawing effect of electronegative atoms.
These atoms cause nearby protons to produce peaks at higher chemical shift values, often in the
range 2.5 to 4.5 ppm.
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Consider the H NMR spectrum of an unknown compound, D, which has a molecular formula
C4H8O2 and is known to have an absorption in its IR spectrum corresponding to a C=O
absorption.

IB Questionbank Chemistry 12
 Use this information and the values in Table 18 of the Data Booklet to deduce the structure of
D.

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................

................................................................................................................................................
(Total 4 marks)

8. Mass spectrometry is a powerful analytical technique used in the identification of organic

compounds. The mass spectrum of a compound with empirical formula CH 2O displays peaks at
m/z 15, 45 and 60.

(a) Determine the molecular formula of the compound.

......................................................................................................................................

......................................................................................................................................
(1)

(b) Identify the fragments responsible for the peaks at

m/z = 15 .......................................................................................................................

m/z = 45 .......................................................................................................................
(2)

IB Questionbank Chemistry 13
 (c) Identify a compound that could produce this spectrum.

......................................................................................................................................

......................................................................................................................................
(1)
(Total 4 marks)

9. The infrared spectrum of a substance, X, with empirical formula C 3H6O is given below.

[Source: NIST http://webbook.nist.gov/chemistry]

(i) Explain why the structural formula of X cannot be:

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)

IB Questionbank Chemistry 14
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(ii) The H NMR spectrum of X consists of three peaks. Deduce the structural formula of X
and the relative areas under each peak.

......................................................................................................................................

......................................................................................................................................
(2)
(Total 4 marks)

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10. H NMR and IR spectroscopy both involve the absorption of electromagnetic radiation.

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(a) (i) Identify the region of the electromagnetic spectrum used in H NMR spectroscopy.

...........................................................................................................................
(1)

(ii) Identify which of these two techniques involves higher energy radiation.

...........................................................................................................................

...........................................................................................................................
(1)

(b) Identify which of the following molecules absorbs IR radiation and explain your choice.

H2 O2 HCl

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................

......................................................................................................................................
(2)
(Total 4 marks)

IB Questionbank Chemistry 15
11. (a) The mass spectrum of an unknown compound, X, of empirical formula C2H4O is shown
below.

[Source: Cleapss Guides: L202 Spectra (Cleapss School Science Service), Sept 2000.]

(i) Determine the relative molecular mass of X from the mass spectrum and deduce
the formula of the molecular ion.

...........................................................................................................................

...........................................................................................................................
(2)

(ii) Identify a fragment which gives rise to the peak at m/z = 29.

...........................................................................................................................
(1)

(iii) Comment on the absence of a peak at m/z = 59.

...........................................................................................................................

...........................................................................................................................
(1)

IB Questionbank Chemistry 16
 (b) The IR spectrum of X is shown below.

[Source: http://modbo1.ibase.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng]

(i) Use Table 17 of the Data Booklet to identify the bonds which correspond to the
absorptions A and B.

A: ......................................................................................................................

B: ......................................................................................................................
(1)

(ii) Deduce the name of the functional group present in X.

...........................................................................................................................
(1)

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(c) (i) The H NMR spectrum of X shows three peaks. State the information that can be
obtained from the number of peaks.

...........................................................................................................................

...........................................................................................................................
(1)

IB Questionbank Chemistry 17
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(ii) The H NMR spectrum of X includes peaks at 2.0 and 4.1 ppm. Use Table 18 of the
Data Booklet to suggest the chemical shift of the third peak and state its relative
peak area. Show your answers in the table below.

Peak Chemical shift / ppm Relative peak area

First 2.0 3
Second 4.1 2
Third
(2)

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(iii) Deduce a possible structure for X that is consistent with the mass, IR and H NMR
spectra.

(1)
(Total 10 marks)

12. Compounds A and B are alcohols with the molecular formula C3H8O. The following
information was obtained from a mass spectrum of each alcohol.

A: peaks at m/z = 29, 31, 60

B: peaks at m/z = 45, 60

(a) Deduce the formula of the species responsible for the peak at m/z = 60.

.....................................................................................................................................
(1)

(b) Deduce the formula of the species with m/z = 31.

.....................................................................................................................................
(1)

IB Questionbank Chemistry 18
 (c) Deduce the structure of each alcohol.

Structure of A

Structure of B

(2)
(Total 4 marks)

IB Questionbank Chemistry 19