Name: _________________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
Reference in textbook:
Book 7, Part XV
Experiment 64.2 See guidelines on investigation
64.2
Ch.64, p.35 on pages T22–T30
Qualitative analysis of an unknown carbon
compound
PowerPoint
Objective
To identify an unknown carbon compound by spectral data and
simple chemical tests. N1 Note 1
Teachers may tell students that the unknown
compound contains carbon, hydrogen and oxygen
atoms only.
Background
The functional group(s) present in an unknown carbon compound can be
found by qualitative analysis. The spectral data from infrared spectrum
and mass spectrum can be used to identify an unknown compound. A
series of simple chemical tests can also be performed to further prove the
identity of an unknown carbon compound.
In this investigation, you are given an unknown carbon compound.
The infrared spectrum and mass spectrum of the compound are provided.
You are going to identify the compound by analysing the spectra and
performing some simple chemical tests.
Materials available
Apparatus: Time required:
♦ Safety spectacles 2 periods
♦ Protective gloves
Chemicals:
♦ Sample of an unknown carbon
compound
(Other apparatus and chemicals may be
provided if necessary.)
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Name: ____________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
Spectral data given
64.2
Infrared spectrum of the unknown carbon compound:
100
Transmittance (%) 80
60
40
20
0
4000 3500 3000 2500 2000 1500 1000 500
–1
wavenumber (cm )
Mass spectrum of the unknown carbon compound:
100
80
Relative abundance (%)
60
40
20
0 10 20 30 40 50 60 70 80
m/e
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Name: _________________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
Safety precautions
64.2
1. You must wear safety spectacles.
2. Seek advice from your teacher for your experimental design before you start.
3. Handle all chemicals with great care. Avoid direct contact of chemicals
with skin.
4. Dispose of chemical wastes, broken glassware and excess materials
according to your teacher’s instruction.
Designing experiment
In your group, discuss how you will carry out the experiment by thinking
of the following points.
1. In the space provided, write down the tests that you are going to
perform.
(1) Test for carbon-carbon double bond by the addition of bromine
(dissolved in organic solvent).
(2) Test for hydroxyl group by the addition of acidified potassium
dichromate solution.
(3) Test for carbonyl group by the addition of
2,4-dinitrophenylhydrazine.
(4) Test for carboxyl group by the addition of sodium carbonate
solution. If there is any gas evolved, test it with limewater.
2. In the space provided, write down the apparatus and chemicals that
you will use.
Apparatus:
• Safety spectacles
• Protective gloves
• Test tubes in rack and with brush
• 1-hole rubber stopper fitted with a bent delivery tube
• 2 rubber stoppers
• Droppers
• A hot water bath
• Heat-resistant mat
Chemicals:
• Bromine (dissolved in organic solvent), 1%
• Acidified potassium dichromate solution (0.01 M)
• 2,4-dinitrophenylhydrazine solution (1.0 M)
• Sodium carbonate solution
• Limewater
• Distilled water
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Name: ____________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
3. In the space provided, write down the step-by-step procedure to carry
out your experiment.
64.2
A. Test for carbon-carbon double bond
3
(1) (a) Add 1 cm of sample to a clean test tube.
(b) Add 2 drops of bromine solution to the sample.
(c) Stopper the test tube and then shake it. Record your
observations.
B. Test for hydroxyl group
3
(2) (a) Add 1 cm of sample to a clean test tube.
(b) Add 2 drops of acidified potassium dichromate solution to the
sample.
(c) Put the test tube into a hot water bath for 3 minutes. Record
your observations.
C. Test for carbonyl group
3
(3) (a) Add 1 cm of 2,4-dinitrophenylhydrazine solution to a test
tube.
(b) Add 3 drops of sample to the test tube. Record your
observations.
D. Test for carboxyl group
(4) (a) Fill a test tube with limewater to a depth of 4 cm. Stopper the
test tube.
3
(b) Add 1 cm of sodium carbonate solution to another test tube.
3
(c) Add 1 cm of sample to the test tube containing sodium
carbonate solution.
(d) Quickly stopper the tube with a rubber stopper fitted with a
bent delivery tube.
(e) Pass any gas evolved through limewater. Record your
observations.
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Name: _________________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
4. What safety precautions, if any, need to be taken in your experiment?
Complete the following risk assessment form by filling in suitable
64.2
information.
Risk assessment form
Hazardous chemicals Nature
Source(s) of
used or made, hazardous of the Safety precautions
information
procedure or equipment hazard(s)
Bromine (dissolved in Toxic, (a) Perform the experiment in 1. Handbook
organic solvent) corrosive fume cupboard.
on Safety in
(b) Make sure the container is
properly stoppered. Avoid Science
breathing in its vapour. Laboratories
(c) Wear a laboratory coat, 2. MSDS
safety spectacles and gloves.
3. CLEAPSS
(d) Avoid contact with the eyes
or skin; when accidentally student safety
spilt into the eyes or onto the sheets
skin, wash the affected area
with running water for at
least 3 minutes and go for
medical check-up.
Acidified potassium Toxic Same as (a), (b) and (c) above.
dichromate solution
2,4-dinitrophenylhydrazine Toxic, Same as (a), (b) and (c) above.
solution explosive (d) Keep away from heat and
naked flame.
(e) Handle with extreme care
– avoid shock or friction.
Sodium carbonate Irritant Avoid contact with the eyes or
solution, limewater skin; when accidentally spilt into
the eyes or onto the skin, wash
the affected area with a lot of
water.
Disposal of residues: Dispose of the wastes into labelled waste bottles Prepared by:
for different kinds of chemicals.
Remarks: Date:
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Name: ____________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
Results
64.2
5. Record your observations.
(Reference to step 1): no observable changes.
(Reference to step 2): no observable changes.
(Reference to step 3): an orange-yellow precipitate forms.
(Reference to step 4): no observable changes.
Discussion
6. Based on the evidences from the infrared spectrum, state the
functional group(s) that is/are present in the unknown carbon
compound.
–1
Since there is a strong absorption at around 1720 cm , the unknown
compound should contain a carbonyl group.
7. Based on the evidences from the mass spectrum, interpret the peak(s)
in the mass spectrum of the unknown carbon compound.
In the mass spectrum, the peak at m/e = 72 is due to the molecular
+ +
ion, CH3COCH2CH3 . The peak at m/e = 57 is due to the CH3CH2CO
+
ion. The peak at m/e = 43 is due to the CH3CO ion.
64 12 HKDSE CHEMISTRY — A Modern View (Second Edition)
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Name: _________________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
8. How do we test for the presence of the following functional groups?
Write an equation for the reaction involved in each case.
64.2
(a) Test for carbon-carbon double bond
(i) Chemical
Test with bromine (dissolved in organic solvent)
reagent(s) used
R1 R3
R1 R3
(ii) Equation C C + Br2 R2 C C R4
R2 R4
Br Br
(b) Test for hydroxyl group
(i) Chemical
Test with acidified potassium dichromate solution
reagent(s) used
O O
(ii) Equation [O] [O]
RCH2OH RC H R C OH
(c) Test for carbonyl group
(i) Chemical
Test with 2,4-dinitrophenylhydrazine solution
reagent(s) used
NO2 NO2
R1 R1
(ii) Equation C O + H2N N NO2 C N N NO2 + H2O
R2 R2
H H
(d) Test for carboxyl group
(i) Chemical
Test with sodium carbonate solution
reagent(s) used
(ii) Equation 2RCOOH + Na2CO3
– +
2RCOO Na + H2O + CO2
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Name: ____________________ ( ) Class: _________ Group: _________ Date: ___________________
Experiment
Conclusion
64.2
9. Briefly summarize the findings of the experiment.
From the spectral data, the unknown compound contains a carbonyl
group and has a molecular mass of 72. The functional group is further
confirmed by the reaction with 2,4-dinitrophenylhydrazine solution.
Based on the above results, together with the fragmentation pattern of
the molecular ion shown in the mass spectrum, the unknown compound
should be butanone.
Prepare a written group report. It should be handed in on
.
Questions
10. State TWO limitations of using infrared spectroscopy in identification
of functional groups.
(1) Some absorption peaks in the spectrum may overlap. In these
cases, broad absorption peaks are recorded.
(2) Not all vibrations give rise to strong absorption peaks.
(3) Not every absorption peak in a spectrum corresponds to a
particular bond or part of the molecule.
(Any TWO)
11. What information can be obtained from the mass spectrum of a
carbon compound?
• The relative molecular mass of the compound
• The structure of the compound
Related exercise in textbook
Book 7
Chapter 64 exercise p.51 Q32
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