CHM 580: Exercise Infrared and Raman Spectroscopy

1. Briefly describe two (2) methods of preparing solid samples for infrared (IR)
spectroscopy.
2. State the purpose of running samples using infrared spectroscopy.
3. State why an IR spectrometer is often purged with dry nitrogen.
4. Based on their IR spectrum, how can you differentiate between a ketone and an
aldehyde?
5. Propanone and 2-propen-1-ol are constitutional isomers. In order to distinguish between
them using IR spectroscopy, provide one (1) absorption peak for each functional group
and its corresponding wavenumber.
6. The IR C=C stretching absorption in symmetrical alkynes are usually absent. Explain why
this is so.
7. Without doing any calculations, which member of each pair do you expect to occur at the
higher frequency?
i) C=C or C=0 Ans:
ii) C=0 or C-O Ans:
8. Briefly describe one (1) method of preparing a solid sample for infrared (IR) spectroscopy
if the solid sample is insoluble in CCI4 or other common IR solvents.
9. In an experiment, a student obtained the IR spectrum of 1-hexanol using a 'neat' liquid.
Explain what a 'neat' liquid means.
10. Identify two peaks which can be found on the IR spectrum of toluene. Based on Appendix
1, state the bonds and the approximate wavenumbers associated with each peak.
11. The following is an IR spectrum of (CH3)2CHCH2CH(OH)CH3. Select two absorption bands
on the spectrum and indicate the bond and wavenumber associated with each peak.

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12. Which of the following molecules will show an IR spectrum: H 2, CO, N2, C02 ?
13. At what approximate wavenumber might the following compounds show one (1) most
obvious IR absorption? Also state the type of bonds which correspond to the
wavenumber you give.
i) CH3COCH3
ii) (CH3)2CHCH2CH=CH2
14. Propanoic acid and methyl ethanoate are constitutional isomers. In order to distinguish
between them using IR spectroscopy, provide one (1) absorption peak for each functional
group and its corresponding wavenumber.
15. A solid compound you wish to analyze has no appreciable solubility in carbon
tetrachloride, carbon disulfide or chloroform. How would you obtain the IR spectrum of
this solid?
16. The following is the IR spectrum of an alcohol, which has the molecular formula C 2H60.
Select three (3) significant peaks associated with the alcohol from the given spectrum.
State the wavenumber and the bond associated with each peak you selected.

17. The following is the IR spectrum of a carboxylic acid, which has the molecular formula
C2H402. Select two significant peaks associated with the carboxylic acid from the given
spectrum. State the wavenumber and the bond associated with each peak you selected.

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18. Assume that you have a compound with molecular formula C 3H60. If the compound has
an IR absorption at 1715 cm-1, what can you conclude?
19. State the requirement for a molecule to be IR active.
20. Which of the following compounds would be expected to show peaks in the IR region?
HF, H2, KCI, N2
21. State the necessary criteria for absorption to occur in the IR region.
22. Cyclohexene and 2-hexyn both have the molecular formula C 6H10. By referring to
Appendix 1, how would you use IR spectroscopy to distinguish between these two
compounds?
23. Name two (2) common solvents used in IR spectroscopy.
24. Propanone and 2-propen-1-ol are constitutional isomers. In order to distinguish between
them using IR spectroscopy, provide one (1) absorption peak for each functional group
and its corresponding wavenumber.
25. State three (3) advantages of using the FT-IR.
26. A Compound shows strong, very broad IR absorption in the region 3300-3600 cm -1 and
strong, sharp absorption at 1715 cm-1. Name one (1) functional group which accounts for
both of these absorptions.
27. The IR C=C stretching absorption in symmetrical alkynes is usually absent. Why is this
so?
28. What is the significance of the fingerprint region in the interpretation of an IR spectrum?
29. Describe the sample preparation of a solid compound using the mull method.
30. Molecules such as 02 and N2 do not absorb infrared radiation. Explain why.
31. Describe how
spectroscopy.
H3C

the

following

compounds

CH3

can

be

distinguished

using

infrared

(IR)

H 3C
CH 3

32. Energy transitions of Rayleigh and Raman scattering for molecule X are shown below.
__________________________________________
E1

__________________________________________
__________________________________________

v3

v2

v1
v0

--------------Potential Energy

------------

--------------

__________________________________________ v3

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v2
E2

__________________________________________ v0
Rayleigh
Anti-Stokes
Stokes

v1

a) Briefly explain the energy transitions of Rayleigh, anti-Stokes and Stokes as appeared
in the above diagram.
b) Sketch a Raman spectrum that may appear for molecule X based on the above
diagram. Label the Rayleigh scattering peak and Raman Stokes and anti-Stokes peak.
c) Justify the use of laser as a radiation source and explain why this radiation is the best
choice in the range of 800 nm region.
33. a) How many normal modes would C2H5NO (acetamide) be expected to have ?
b)
i) Briefly explain why a C=O bond stretch occurs at 1750 cm -1 while a C-O stretch
occurs at 1100 cm-1.
ii) Calculate the wavelength of the C=O bond stretch.
c)
Below is the Raman spectrum of CCl 4, excited by laser radiation at a wavelength
() of 488.0 nm.
(REFER TO FINAL QUESTION JUNE 2013)
i) Using an energy level diagram , explain the Raman shifted peaks.
ii) Why is a laser used as the radiation source?
iii) What is the expected Raman spectrum if a laser source of 632.8 nm is used instead of
488.0 nm?
Explain.
34. a) Describe how a molecule absorbs IR radiation.
b) Name and describe the most widely used IR transducer and briefly explain how it works.

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IR Spectroscopy Tutorial: How to analyze IR spectra

If you have followed this tutorial group-by-group, you will realize that in even rather simple,
mono-functional molecules there are so many IR bands that it is not feasible to assign every
band in an IR spectrum. Instead, look for tell-tale bands -- the region from 4000-1300 cm -1 is
particularly useful for determining the presence of specific functional groups. You can rely on
the IR correlation charts but we recommend that you memorize the distinctive bands of the
common functional bands:
3500-3300 cm-1

NH stretch

3500-3200 cm-1

OH stretch

cm-1
cm-1
cm-1
cm-1

CH stretch
CH stretch
C=O stretch
C=C stretch

3100-3000
3000-2850
1760-1665
1680-1640

1o /2o amines
alcohols, a broad, strong
band
alkenes
alkanes
ketones, aldehydes, esters
alkenes

1. Begin by looking in the region from 4000-1300. Look at the CH stretching

bands around 3000:
Indicates:
Are any or all to the right of 3000?

alkyl groups (present in most organic

molecules)

Are any or all to the left of 3000?

a C=C bond or aromatic group in the

molecule

2. Look for a carbonyl in the region 1760-1690. If there is such a band:

Indicates:
Is an OH band also present?

a carboxylic acid group

Is a CO band also present?

an ester

Is an aldehydic CH band also present?

an aldehyde

Is an NH band also present?

an amide

Are none of the above present?

a ketone
(also check the exact position of the carbonyl band for clues as to the type of carbonyl
compound it is)
3. Look for a broad OH band in the region 3500-3200 cm-1. If there is such a
band:
Indicates:
Is an OH band present?

an alcohol or phenol

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4. Look for a single or double sharp NH band in the region 3400-3250 cm -1. If
there is such a band:
Indicates:
Are there two bands?

a primary amine

Is there only one band?

a secondary amine

5. Other structural features to check for:

Indicates:
Are there CO stretches?

an ether (or an ester if there is a carbonyl

band too)

Is there a C=C stretching band?

an alkene

Are there aromatic stretching bands?

an aromatic

Is there a CC band?

an alkyne

Are there -NO2 bands?

a nitro compound

IR/RAMAN/CHM580/May2015