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Spectral Analysis
Abid Khan
2897438 | WEEK 3 & 5 FRIDAY 8AM
Abstract
The aim of this investigation was to determine the structure of a given unknown organic compound by
conducting functional group tests and deducing its identity through IR and NMR spectroscopy.
Functional group tests were conducted to identify a preliminary understanding of the functional groups
present. Infrared and Nuclear Magnetic Resonance Spectroscopy were used to further identify the
functional groups present and the compounds carbon-hydrogen framework. Three potential
compounds, namely 2-pentanone, 3-pentanone and 1-pentanal, were listed as the possible unknown
compound. After observing the qualitative observations during the functional group tests and spectral
analysis, it was determined that the unknown compound was 2-pentanone.
Introduction/Aim
The study of organic-containing compounds and their properties is called organic chemistry. Organic
chemistry plays a vital role for understanding living systems. The synthetic fibres, plastics, artificial
sweeteners, and drugs that are an accepted part of modern life are products of organic chemistry
(Zumdahl, 2005). An important part of organic compounds are functional groups. A functional group
is a specific group of atoms within a molecules that is responsible for the characteristic chemical
reactions of that molecule (Marie, 2014). They are attached to the carbon backbone of organic molecules
and are far less stable than the carbon backbone so they are likely to participate in chemical reactions
(Fromm, 1997). Functional groups are important as a specific set of functional groups in any given
organic compound specifies its role and chemical behaviour (Dallas Learning Solutions, 2014).
Determining the structure of atoms and molecules of organic compounds can come from studying their
interaction with light (Michigan State University, 2000). Different regions of the electromagnetic
spectrum provide different kind of information as a result of such interactions. The three types of
spectroscopy that will be utilised in this investigation are infrared spectroscopy (IR), nuclear magnetic
resonance spectroscopy (NMR) and mass spectroscopy. The infrared region of the electromagnetic
spectrum covers the range from just above the visible range (7.8 10-7m) to 10-4m (McMurry, 2011).
Absorption of this lower energy radiation causes vibrational and rotational excitation of groups of atoms
within the molecule (Michigan State University, 2000). Since different functional groups have different
characteristic absorptions, identification of functional groups through IR spectroscopy is easily
accomplished (Michigan State University, 2000). NMR spectroscopy is the most valuable spectroscopic
technique available for laboratory organic chemists for structure determination (McMurry, 2011).
Absorption in the low energy radio frequency part of the electromagnetic spectrum causes excitation of
nuclear spin states and are tuned to certain nuclei (1H, 13C, 19F and 31P) (Michigan State University,
2000). For a given type of nucleus, NMR spectroscopy distinguishes and counts atoms in different
locations in the molecule (Michigan State University, 2000).
Abid Khan
The aim of this investigation is to determine the structure of a given unknown organic compound by
conducting functional group tests and deducing its identity through IR and NMR spectroscopy.
Methods
For the methods of this investigation, please refer to pages 10-23 of the 2014MSC Organic Chemistry
Laboratory Manual 2014 edition.
Results
The results section contains tables and descriptions presenting the recorded qualitative observations for
the functional groups and elements testing and physical constants (boiling point and refractive index),
solubility and oxygen flask test results for the unknown compound. These data can be analysed to form
a preliminary understanding of the identity and structure of the unknown compound. A brief description
of each of the functional group tests along with its chemical equation or reaction mechanism are
illustrated. The findings from the IR, NMR and mass spectroscopy for the unknown compound are
presented to assist in deducing the identity of the organic compound. The IR, NMR and mass
spectroscopy spectra can be found in the Appendix. Three potential compounds are then listed with
their physical constants along with their respective chemical structures.
Qualitative Observations
Table 1.1, presented on page 3, presents the qualitative observations that were observed while
conducting the standard functional group and element tests that were conducted by oxygen flask
method. The colour and opacity of the resulting solution, along with whether a precipitate (ppt) was
present, were noted for each of the tests.
Table 1.2, presented on page 4, presents the qualitative observations for the unknown organic
compound. The results detail the observations and whether the unknown compounds are positive or
negative to the standard functional group tests which can then be used to identify the functional groups
present.
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Table 1.1 Qualitative observations from the Standard Functional Group/Element Tests
Cyclohexene
Cyclohexane
Cyclohexene
Carbon-carbon
double bond
Benzyl Alcohol
2.a - Solubility of alcohol and
phenol in base
2.b - Reaction of phenol with ferric
chloride
2.c - Reaction with phenol and
aqueous bromine
2.d - Luca's Test for tertiary
aliphatic alcohol
3.a - Reaction of carboxylic acid
with sodium bicarbonate
Phenol
Phenol
Glucose
clear
White
cloudy colour
change, ppt formed
2 phases, cloudy in the
bottom, clear on top
Not soluble, crystal ppt
formed
Opaque orange-red colour,
ppt formed
Milky colour change, ppt
formed
Silver mirror, dark green,
ppt formed
Dark red, opaque, ppt
formed
Benzaldehyde
Phenol
Tert-butyl
alcohol
Hydroxyl group
Benzoic acid
Acetophenone
Ketone group
Acetophenone
Methyl ketone
Benzaldehyde
Benzaldehyde
Aldehyde group
Methyl Benzoate
Ester group
Aniline
Acetanilide
Aniline
Amino Group
m-dinitrobenzene
Nitro group
Diethyl ether
Ether group
White ppt
Sulphur ion
Chlorine,
bromine,
iodine ion
Nitrogen ion
Ethyl acetate
Aromatic group
Glucose
Carbohydrate
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Aniline
White ppt
Table 1.2 Qualitative Observations from the Functional Group/Element Testing for the
Unknown Organic Compound
Table 1.2 - Qualitative Observations from Functional Group/ Element Testing For Unknown Compound
Positive/Negative with
Functional
Standard Functional Group
Station Number/Reaction Name
Group/Element Test
Observation
test
Red colour, no ppt,
positive with cyclohexane
1.a - Reaction with bromine
soluble
standard
Carbon-carbon
Strong violet
positive with cyclohexane
1.b Reaction with permanganate
double bond
colour, no ppt
standard
2.a - Solubility of alcohol and
positive with benzyl alcohol
phenol in base
Clear
standard
2.b - Reaction of phenol with ferric
Slightly yellow
chloride
colour change
negative
2.c - Reaction with phenol and
aqueous bromine
Red colour change
negative
2.d - Luca's Test for tertiary
aliphatic alcohol
Hydroxyl group
Clear, transparent
negative
3.a - Reaction of carboxylic acid
Carboxylic Acid
Soluble, no sound
with sodium bicarbonate
group
heard
negative
Orange colour, ppt
3.b(i) - D.N.P Test
Ketone group
formed
positive
Opaque, cloudy, no
3.b(ii) - Iodoform Test
Methyl Ketone
ppt
negative
Clear, transparent,
3.c (i) - Tollen's test
no ppt
negative
3.c (ii) - Reduction of Fehling's
N.R, no colour
solution
change from blue
negative
3.c (iii) - Reaction of aldehyde with
Opaque, dark
permanganate
violet
positive
3.c (iv) - D.N.P Test
Aldehyde group
Ester group
Amino group
Ether group
Sulphur ion
Chlorine, bromine,
iodine ions
positive
positive
negative
negative
negative
Purple, no ppt
Brown colour
change
negative
Clear, NR
negative
negative
Nitrogen ion
Clear, no ppt
Clear, no colour
change
Aromatic group
No smokey flame
negative
Carbohydrate
negative
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Nitro group
positive
negative
When cyclohexene reacts with the purple potassium manganate (VII), manganese dioxide is formed
and induces a brown colour change.
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Benzyl alcohol has a broad absorption at 3400 - 3650 cm-1 while toluene does not. Toluene can be
resonance stabilised. The resonance hybrid suggests all six C=C bonds of benzene are more than the
single bonds but not complete double bonds as they only have partial pi character.
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3.a Reaction of carboxylic acid with sodium bicarbonate and comparison of IR spectrum of benzoic
acid and toluene
Carboxylic acids are soluble in aqueous sodium bicarbonate. In this reaction, the crystal of benzoic acid
is dissolved and forms colourless sodium ethanoate.
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Benzoic acid has characteristic absorptions for carbonyl group 1670 1780 cm-1, hydroxyl group at
2500 - 3100 cm-1 and C-O bond at 1210 1320 cm-1 which toluene does not have. These characteristics
are the stretching frequencies for carboxylic acid.
3.b (i) D.N.P Test with acetophenone
The D.N.P test with acetophenone is used to determine whether a ketone group is present. The following
reaction mechanism outlines this reaction
Abid Khan
3.b (ii) Iodoform Test test for methyl ketones and IR spectrum of acetophenone
The following reaction is used to determine whether a methyl ketone is present. Iodine is decolourised
indicating that one of the reactants were a methyl ketone.
Acetophenone has a carbonyl group that is part of the functional group. The stretching frequency of this
group is 1670 1780 cm-1.
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Amide
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Alkyl group
Isopropyl group
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Table 1.4 - Observations after the analysis of 1H NMR spectra of the unknown compound
4 signals/peaks are observed in the 1H NMR spectra of the unknown compound.
Table 1.4 - Observations after the analysis of 1H NMR spectra of the unknown compound
Triplet @ 0.93 ppm
3H
2H
3H
2H
Table 1.5 - Observations after the analysis of 13C NMR spectra of the unknown compound
Observations after the analysis of 13C NMR spectra of the unknown compound
Peak @ 13.7 ppm
Primary Alkyl
Peak @ 208.93
Aldehyde/Ketone
Potential Compounds
After observing both the IR and NMR spectra, it can be deduced that the compound is either an
aldehyde or a ketone as both these functional groups are present in the IR and 13C NMR spectra.
Three possible compounds that are clear liquids and have a boiling point near 102oC are: 2-pentanone,
3-pentanone, 1-pentanal. These compounds were suggested by the convenor of 2014MSC Organic
Chemistry.
Name: 2-pentanone
B.P: 101oC - 102oC
Name: 3-pentanone
B.P: 100oC - 102oC
Name: 1-pentanal
B.P: 102oC - 103oC
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Discussion
The identity of the given unknown organic compound can be deduced by analysing: the qualitative
observations and whether the functional group tests were positive or negative, the NMR spectra to
determine the number of carbon atoms and different proton environments and the IR spectra to further
deduce what functional groups were present. The structures of 2-pentaanone, 3-pentanone and 1pentanal will be examined using the results that have been obtained.
In table 1.2 the unknown compound had positive reactions with following functional group tests:
carbon-carbon double bond group, hydroxyl group, ketone group, aldehyde group, ester group and ether
group. This finding indicates that the unknown compound could contain one or more of these functional
groups.
The IR spectra results can be used to further narrow down the actual composition of the functional
groups. As seen from the IR spectra located in the appendix and tabulated in table 1.3, there is a sharp
peak at the absorption frequency of 1680 1780 cm-1. This indicates that there functional group present
could be a ketone, ester, carboxylic acid or an aldehyde. Furthermore, there is a medium/sharp peak at
the absorption frequency of 2853 2962 cm-1 suggesting that there are alkyl groups in the unknown
compound. Lastly, there is medium peak at the absorption frequency of 1385 1395 cm-1 indicating
that there are isopropyl groups present in the compound. After analysing the IR spectra findings, the
following potential groups that were hypothesised from the findings in table 1.2 can be rejected:
hydroxyl group, ether group and carbon-carbon double bond group.
To determine the actual structure and carbon backbone of the unknown compound, the NMR spectra
results in table 1.4 and table 1.5 will be analysed. As shown in table 1.5 and the 13C NMR spectra in the
appendix, there are five peaks indicating that there are five different carbon environments in the
unknown compound. This seems to suggest that 3-pentanone is not the unknown compound as it does
not contain 5 different carbon environments. This is highlighted in figure 1.1. The different carbon
environments are shown by the coloured circles.
Figure 1.1 Carbon environments in 3-pentanone
As it can be seen in figure 1.1, there are only 3 different
carbon atoms thus 3-pentanone cannot be the unknown
organic compound.
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To distinguish between 2-propanone and 1-pentanal, as both compounds have five different carbon
environments, the 1H NMR spectra results will be analysed to identify their different proton
environments. Both compounds have 4 different proton environments. In table 1.4 and from the 1H
NMR spectra in the appendix, it can be observed that there is singlet at 2.13ppm. This suggests that the
proton group at 2.13ppm has no neighbouring protons. This finding appears to eliminate 1-pentanal as
the unknown compound as each proton environment has at least one neighbouring proton. This is
illustrated in figure 1.2 by using the program Chemdraw.
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Conclusion
The aim of this investigation was to determine the structure of a given unknown organic compound by
conducting functional group tests and deducing its identity through IR and NMR spectroscopy. After
observing the qualitative observations during the functional group tests and spectral analysis, it was
determined that the unknown compound was 2-pentanone.
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Appendix
IR Spectrum of Unknown Organic Compound
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References
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