Department of Chemistry

CEM2005W 2024
Problem Sheet 1

Question 1
Consider molecules A to E.

a) Identify the number of conjugated double bonds present in molecules A to E

b) Which molecule(s) will absorb UV radiation detectable by the spectrometer (200 to 400 nm),
briefly justify your selection.

c) Which molecule(s) will have colour i.e. absorb visible radiation (400 to 800 nm), briefly justify
your selection.

d) Rank the following molecules from longest to shortest λmax. Explain your choice particularly
for order for molecules B and D.

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Note: These materials are for educational purposes and for your personal use and may not be shared, distributed, sold or placed on any third-party websites without
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Question 2
Consider molecules A to F.
A. B. C.
CH2 CH C N
H2C

CH3 H
D. O E. F.
C C
C CH3 CH2
O CH2

a) Identify the number of conjugated double bonds present in molecules A to F

b) Which molecule A to F will have the longest λmax. Briefly explain.

Question 3
In UV-visible absorption spectroscopy, which of the following statements is incorrect? Briefly explain.

A UV-visible spectroscopy is based on electronic transitions

B n→π * transitions are higher in energy than π→π* transitions
C A conjugated system of double bonds in a molecule shifts the absorption maxima to longer
wavelengths
D σ→σ* transitions are higher in energy than π→π* transitions
E Absorbance is proportional to both the path length and concentration of the absorbing
species

Question 4
Which of the following statements regarding IR spectroscopy is incorrect? Briefly explain.

A Infrared spectra record the transmission of IR radiation.

B Molecular vibrations are due to periodic motions of atoms in molecules, and include bond
stretching, torsional changes, and bond angle changes.
C Infrared spectra give information about bonding features and functional groups in molecules.
D Bonds to hydrogen have higher stretching frequencies than those to heavier atoms.
E Triple bonds have lower stretching frequencies than corresponding double bonds, which in
turn have lower frequencies than single bonds.

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Note: These materials are for educational purposes and for your personal use and may not be shared, distributed, sold or placed on any third-party websites without
the permission of the University.
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Question 5
The infrared spectrum of an organic compound is shown below.

The compound could be:

A propene
B propyne
C 2-propanol
D propanoic acid
E propanone (CH3COCH3).

Question 6
Label the key IR absorptions and identify the correct structure A to E
(use the IR tables in SPEC3).

Answer =

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Note: These materials are for educational purposes and for your personal use and may not be shared, distributed, sold or placed on any third-party websites without
the permission of the University.
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Question 7
Complete the table on the spectral characteristics of the three compounds

UV absorption
> 220 nm

Give two
diagnostic IR
stretches &
approx. cm-1
# proton NMR
signals

# carbon NMR
signals

© University of Cape Town. All rights reserved.

Note: These materials are for educational purposes and for your personal use and may not be shared, distributed, sold or placed on any third-party websites without
the permission of the University.
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