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UNIVERSITI TEKNOLOGI MARA

FAKULTI KEJURUTERAAN KIMIA


INSTRUMENTAL LABORATORY
(CHE 515)

NAME
(2010562001)

: IHSAN SABRI BIN ROSLI


MOHAMAD FADHLI BIN SAMSUDIN

(2010744793)
MUHAMMAD JAZVIR B. SULAIMAN
(2010130933)
MUFIDAH BINTI MAHFUZ
(2010529669)
ROHAZIERAH BT CHE OMAR
(2010128483)
GROUP

: EH2214A

EXPERIMENT
DATE SUBMITTED
SEMESTER

:
: 21 NOVEMBER 2012
:4

PROGRAMMED / CODE
SUBMIT TO

: DR KAMARIAH NOOR ISMAIL

Title
Abstract
Introduction
Theory
Experimental Protocol
Results
Discussion
Conclusion
References
TOTAL
Remarks

: EH 221

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TABLE OF CONTENTS

TITLE

PAGE

Abstract

Introduction

4-5

Theory

6-8

Procedure

Results

10-12

Discussions

13-22

Conclusions

23

References

24

ABSTRACT

The experiment was conducted to determine and draw the structure for unknown
compound A to I. The experiment for solid and liquid samples has almost the same
preparations way. The difference is only when for solid, it need to be dissolved first before
been transferred into NMR tube. Then for both solid and liquid samples, three drops of a
deuterated solvent (usually chloroform) is added into the tube. Then, the tube is wrapped in a
tissue for padding before inserted it into a holder of the centrifuge. Spectral window is setting
by modify the appearance and the spectrum is printed. From the analyses that have been
done, each unknown compound was determined. The IUPAC name for compound A is 2, 4dimethylfuran-3(2H)-one, whereas compound B is 2-methylcyclopentane-1, 3-dione. Next,
compound C,D, and E are cyclohexane-1,4-dione, ethenyl (2E)-but-2-enoate, and 2methylprop-2-enoate respectively. In addition, the analysis on compound F shows that it is
cyclobutylideneacetic acid, while compound G and compound H are (5-methylfuran-2-yl)
methanol and -hydroxy-3-methylcyclopent-2-en-1-one respectively. The last compound that
been analyzed was compound I, that is hex-2-ynoic acid.

INTRODUCTION
Nuclear magnetic resonance spectroscopy (NMR) is the technique to determining the
structure of organic compounds. It is the only one for which a complete analysis and
interpretation of the entire spectrum is normally expected. Understanding the physical
principle on which the methods are based is important to make sure it is success in using
NMR as an analytical tool. The nuclei of many element isotopes have a characteristics spin.
This includes 1H and 13C (but not 12C). The NMR behaviour of 1H and 13C nuclei has been
exploited by organic chemist since they provide valuable information that can be used to
deduce the structure of organic compounds. Magnetic field will develop since a nucleus is a
charged particle in motion. 1H and 13C have nuclear spins of 1/2 and so they behave in a
similar fashion to a simple, tiny bar magnet. When a field is applied they line up parallel to
the applied field, either spin aligned or spin opposed but in the absence of a magnetic field,
these are randomly oriented. Two schematic representations of these arrangements are shown
below:

There are two general types of NMR instrument which is continuous wave and
Fourier transform. Early experiments were conducted with continuous wave (C.W.)
instruments, and in 1970 the first Fourier transform (F.T.) instruments is introduced.
Continuous wave NMR spectrometer is in principle to optical spectrometer. The
sample is held in a strong magnetic field, and the frequency of the source is slowly scanned.
The magnitude of the energy changes involved in NMR spectroscopy is small. This means
that sensitivity is a major limitation. One way to increase sensitivity would be to record many
spectra, and then add them together; because noise is random, it adds as the square root of the
number of spectra recorded. Because of this, Fourier transform (F.T.) instruments became
available. In FT-NMR, all frequencies in a spectrum are irradiated simultaneously with a
radio frequency pulse. Following the pulse, the nuclei return to thermal equilibrium. A time
domain emission signal is recorded by the instrument as the nuclei relax. A frequency domain
spectrum is obtained by Fourier transformation.
The NMR instrumentation is shown as below;

Figure 1: basic arrangement of an NMR spectrometer


The sample is positions in the magnetic field and excited via pulsations in the radio frequency
input circuit. The realigned magnetic field induced a radio signal in the output circuit which
is used to generate the output signal. Fourier analysis of the complex output produces the
actual spectrum. The pulse is repeated as many times as necessary to be identified from the
5

background noise. The pulse is actually a signal of frequency, F, is turned on and then off
again very rapidly, then the result is an output consisting of many frequencies centred
about F with a bandwidth of 1/t, where t is the duration of the pulse. This means that
radiation is produced of all frequencies in the range F 1/t. If t is very small, then a large
range of frequencies will be produced simultaneously, and all target nuclei in a sample will be
excited.

THEORY
Basic principles of NMR
Nuclei with an odd mass or odd atomic number have nuclear spin. In the presence of
an applied external magnetic field, 1H

13

C nuclei exist in two nuclear spin states of different

energy. The difference in energy between the two spin states is dependent on the external
magnetic field strength and is always small. . The spin states energy difference shown from
the equation below:
E=

h
B
2 0

Where: h = Plancks constant


B0 = strength of external magnetic field
= gyromagnetic ratio, is the constant which is a property of the particular
nucleus

In the absence of a magnetic field, these are randomly oriented but when a field is
applied they line up parallel to the applied field, either spin aligned or spin opposed. The
arrangements of the spin orientation are shown below:

Figure 1: Spin orientation

Chemical Shift
An NMR spectrum is a plot of the radio frequency applied against absorption. A
signal in spectrum is known as resonance and frequency of signal is chemical shift. In other
word, chemical shift is defined as the frequency of the resonance expressed with reference to
a standard compound which is defined to be at 0 ppm. The scale is in parts per million and it
is independent of the spectrometer frequency.

In an NMR spectrum, a peak at a chemical shift of 10 ppm is said to be downfield or


deshielded with respect to a peak at 5 ppm and the peak at 5 ppm is upfield or shielded with
respect to the peak at 10 ppm.

There are several factors that may affect the chemical shift. This means that different types of
proton will occur at different chemical shifts. The various factors include:
a) Electronegativity effect
The resonance position of protons bonded to carbon is shifted downfield by
electronegativity elements also bonded to the carbon. The electronegativity element
wtithdraws electron density from the carbon and its directly bonded protons which
diminished the magnitude of magnetic field. Thus, the higher the electronegativity of
the directly bonded atom, the larger the downfield shift.

Figure 2: The effect of electronegativity element on chemical shift


b) Magnetic Anisotropy
Anisotropy means non-uniform. Magnetic anisotropy means that there is a
non-uniform magnetic field. Electron in

systems such as aromatics, alkenes,

alkynes, carbonyl and others interact with the applied field which induced a magnetic
field that causes the anisotropy. The effects of anisotropy are the nearby proton will
experience three fields which is the applied field, the shielding field of the valence
electron and the field due to the

system. Thus, shielded (smaller ) or deshielded

(larger ) and also energy required as well as the changes of frequency absorption are
depend on the position of the proton in the this third field. Figure 3 shows schematic
representation of anisotropy effect.

Figure 3 : Anisotropy effect


c) Hydrogen Bonding
Protons that are involved in hydrogen bonding usually OH and NH have a
large range of chemical shift values. The more hydrogen bonding there is, the more
protons are deshielded and the higher its chemical shift will be. However, it is difficult
to predict since the amount of hydrogen bonding is susceptible to several factor such
as salvation, acidity, concentration and temperature.

PROCEDURE
8

Sample preparation for liquid


1. Sample liquid is transfer into the NMR tube by using long-tipped Pasteur pipette.
2. About three drop of a deuterated solvent (usually chloroform) is added into the tube.
3. Then, the tube is caped and spins in the hand centrifuge to collect the residual sample
from the walls and collapse air pockets and bubbles.
4. The tube is wrapped in a tissue for padding before inserted it into a holder of the
centrifuge.
5. A thin strip of Parafilm around the seam between the tubes and its cap is wrapped to
prevent the sample from drying out.
6. The tube is labeled.
Sample preparation for solid
1. A small amount of solid used is measured at the end of spatula. Then, sample solid is
put into a small test tube.
2. About three drop of a deuterated solvent (usually chloroform) is added into the tube.
Noted that the NMR will NOT work if deuterated solvent is not used!
3. The solid sample is dissolved and the solution is transferred into the NMR tube.
4. The tube is caped and spins in the hand centrifuge to collect the residual sample from
the walls and collapse air pockets and bubbles.
5. The tube is wrapped in a tissue for padding before inserted it into a holder of the
centrifuge.
6. A thin strip of Parafilm around the seam between the tubes and its cap is wrapped to
prevent the sample from drying out.
7. The tube is labeled.
NMR Operating Procedure
1. Lock on the sample is obtained by adjusting the knob on the side of the keyboard.
2. The sample is then locked and shimmed the magnetic field. The shimming is repeated
until a maximum lock is achieved.
3. The experiment on the sample is run and the parameter for 1D NMR spectrum is set.
4. The spectral window is setting by modify the appearance and the spectrum is printed.
5. The data is obtained and saved automatically.

RESULTS
Compound
A

Chemical shifts, (ppm)


1

5.4 (1, s)
4.5 (1, qrt)
9

Functional groups

Esters, RCO2-CH

R2C=CH2

2.2 (3, s)

Sat. alkanes , R-H

1.4 (3,d)

Sat. alkanes, R-H

189.8

Ketone, R2C=O
Aldehydes, RCH=O
Ester, R-CO2R

103.5

R2C=CH2

82.8

C-OR

16.9

Sat. alkane, R-H


Sat. alkane, R-H

Sat. alkane, R-H

2.2 (1,qrt)

Sat. alkane, R-H

1.5 (3,d)

Sat. alkane, R-H

194

Ketone, R2C=O

111.6

Aromatics

30.1

C-CO-R

5.7

Sat. alkane, R-H

2.7 (8,t)

Sat. alkane, R-H

208.3

Ketone, R2C=O

37.6

C-CO-R

7.4 (1,t)

Alkene, RCH=CHR

7.1 (1,qnt)

Alkene, RCH=CHR

5.9 (1,d)

Alkene, RCH=CHR

4.7 (2,d)

Ester, RCO2-CH

1.9 (3,d)

Sat. alkane, R-H

163.2

Ester, RCO2-CH

147

R2C=CH2

141.3

Alkene, RHC=CHR

121.7

Alkene, RHC=CHR

97.4

C-OR

18.2
7.3 (1,t)

Sat. alkane

Alkene, RHC=CHR

6.0 (2,s)

Alkene, RHC=CHR

4.7 (2,d)

Ester, RCO2-CH

205.6

13

16.3
2.4 (4,t)
1

B
13

13

13

10

13

13

13

H
1

13

2.0 (3,s)

Sat. alkane

164.3

Ester, R-CO2R

141.5

Alkene, RHC=CHR

135.5

Alkene, RHC=CHR

127.2

Alkene, R2C=CH2

97.8

C-OR

18.2

Sat. alkane

11.3 (1,s)

Carboxylic acid, RCO2H

5.5 (1,s)

Alkene, RHC=CHR

2.5 (2,t)

Sat. alkane

2.4 (2,t)

Sat. alkane

2.0 (2,qnt)

Sat. alkane

193

Carboxylic acid, RCO2H

104.3

Alkene, R2C=CH2

32.3

Sat. alkane

21.1

Sat. alkane

6.1 (1,d)

Alkene, RHC=CHR

5.9 (1,d)

Alkene, RHC=CHR

4.5 (2,s)

Alkene, R2C=CH2

2.3 (1,s)

Alcohol, -ROH

2.3 (3,s)

Sat. alkane

152.6

Alkene, RHC=CHR

152.1

Alkene, RHC=CHR

108.6

Alkene, RHC=CHR

106.3

Alkene, R2C=CH2

57.1

Alcohol, C-OH

13.5

Sat. alkane

6.7 (1,s)

Alkene, RHC=CHR

2.4 (2,t)

Sat. alkane

2.3 (2,t)

Sat. alkane

2.0 (3,s)

Sat. alkane

203.8

Ketone, R2C=O

11

I
13

149.5

Alkene, R2C=CH2

145.9

Alkene, RHC=CHR

32.1

C-C=C

27.3

Sat. alkane

14.4

Sat. alkane

9.7 (1,s)

Carboxylic acid, RCO2H

2.3 (2,t)

Sat. alkane

1.6 (2,sxt)

Sat. alkane

1.0 (3,t)

Sat. alkane

158.5

Carboxylic acid, RCO2H

92.6

Alkyne

72.9

Alkyne

21.0

Sat. alkane

20.7

Sat. alkane

13.4

Sat. alkane

DISCUSSION
We are required to determine and draw a viable structure for compound A to I. From
the elemental composition and the relative molecular mass of the given compound, we can
determine the number of carbon, hydrogen and oxygen present in the compounds. The
calculations involved are shown below:
Elemental composition: C 64.3%, H 28.6%, O 7.2%
Relative molecular mass of the compounds: 112.1 gmol-1
12

Relative atomic mass: C 12.01gmol-1, H 1.01gmol-1, O - 16gmol-1


Total % = 100.1%

Number of carbon, C present is:


64.3
1
1
112.1 gmol =72.01 gmol
100.1
1

72.01 gmol
=6
1
12.01 gmol

Number of hydrogen, H present is:


7.2
1
1
112.1 gmol =8.063 gmol
100.1
8.063 gmol1
=7.98 8
1.01 gmol1

Number of oxygen, O present is:


28.6
112.1 gmol1=32.028 gmol1
100.1
32.028 gmol1
=2
16 gmol1

Hence, from the above calculation, the molecular formula for the compounds to be
determined is C6H8O2

Compound A

the IUPAC name for this compound is 2, 4-dimethylfuran-3(2H)-one

H NMR

13

O
CH3

H3C
O

13

C NMR

O
CH3

H3C
O

The possible structure for compound A is 2, 4-dimethylfuran-3(2H)-one. Based on the


data that had been given in experiment, we know that compound A has 6 peaks for C and 4
peak for H. For 13C NMR, one of the chemical shifts that given in the experiment is 205.6
ppm. From the table of chemical shift (refer above 200 ppm), the functional group that
present is carbonyl group which is aldehyde and ketone. For aldehyde, it must have 1H NMR
chemical shift in the range of 9 ppm to10 ppm whereas for ketone, it must have 1H NMR
chemical shift in the range of 2 ppm to 3 ppm. So, it is proved that ketone present in the
compound A because the compound shows 1H NMR chemical shift in the range of 2 ppm to3
ppm. Besides that, compound A must have double bond because it has chemical shift in the
range of 100 ppm until 200 ppm, that is for 1H NMR, the range of chemical shift in the range
of 5 ppm to 6.5 ppm. Based on the structure above, it shown that C that attached to the O
group (C=O) will have higher chemical shift because the presence of strong electronegative
element that decrease the electron density.

Compound B

the IUPAC name for this compound is 2-methylcyclopentane-1, 3-dione


14

H NMR

H3C
O

13

C NMR

H3C
O

For compound B, the possible structure is 2-methylcyclopentane-1, 3-dione . From the


value given, we can identify the functional group for the compound. From the

13

C NMR

Chemical Shifts, it have -194.0 (ketone / aldehyde), 111.6 (alkene), 30.1 (alkene) and 5.7
(alkanes). Then, for 1H NMR Chemical Shift, it have

-2.4 and 2.2 (ketone / alcohol), and

1.5 (alkanes). In this compound, it consists of several functional group include ketone,
cycloalkane. In 1H NMR, for (4,t), it has three peaks where it has two carbon (contain four
hydrogen) next to carbon that has two hydrogen. For (1,qrt), it has four peaks where it has
carbon (contain one hydrogen) next to carbon that has three hydrogen. Lastly (3, d), it has
two peaks where it has carbon (contain three hydrogen) next to carbon that has one hydrogen.
3H has lowest chemical shifts because in shielded area. 1H has higher chemical shift because
next to pi system and 2H has highest chemical shift because higher in hydrogen bonding and
next to pi system.

15

Compound C

the IUPAC name for this compound is cyclohexane-1,4-dione

H NMR

13

C NMR

O
For compound C, the possible structure is cyclohexane-1, 4-dione. From the value
given, we can identify the functional group for the compound. From the 13C NMR Chemical
Shifts, it have -208.3 (ketone / aldehyde) and 37.6 (ketone / alkene / alkanes). Then, for
1

H NMR Chemical Shift, it has

-2.7 (ketone). For this compound, it must have

symmetric compound which it has two peaks, so it has same value of chemical shift. In this
compound, the most accurate compound consists of ketone and cycloalkane functional group.
In 1H NMR, for (8,t), it means that each side contains two carbon where each carbon contain
two hydrogen.

16

Compound D

the IUPAC name for this compound is ethenyl (2E)-but-2-enoate

H NMR

O
H3C

CH2

CH2

13

C NMR

O
H3C

For compound D, the possible structure is ethenyl (2E)-but-2-enoate. From the value
given, we can identify the functional group for the compound. From the 13C NMR Chemical
Shifts, it have -163.2 (ester / alkene), 147.0 (alkene / aromatic), 141.3 and 121.7 (alkene),
97.4 (aromatic) and 18.2 (alkene / alkanes). Then, for 1H NMR Chemical Shift, it has

7.4 and 7.1 (aromatic), 5.9 and 4.7 (alkene), and 1.9 (alcohol / alkene). For this compound, it
is a straight chain carbon. It consists of some functional group include alkene, alkanes and
ester group. In 1H NMR, it consist of (1,t), means that it has three peak where it has carbon
(contain one hydrogen) next to carbon that has two hydrogen. For (1,qnt), it has five peaks
where it has carbon (contain one hydrogen) next to carbon that has four hydrogen. For (1,d),
it has two peaks where it has carbon (contain one hydrogen) next to carbon that has one

17

hydrogen. For (2,d), it has two peaks where it has carbon (contain two hydrogen) next to
carbon that has one hydrogen. Then, for (3,d), it has two peaks where it has carbon (contain
three hydrogen) next to carbon that has one hydrogen. (1H, t) has highest chemical shift value
because located beside the electronegative element (O).

Compound E

the IUPAC name for this compound is ethenyl 2-methylprop-2-enoate

H NMR

O
H2C

CH3

O
H2C

13

C NMR

O
H2C

CH3

O
H2C

For compound E, the possible structure is ethenyl 2-methylprop-2-enoate. From the


value given, we can identify the functional group for the compound. From the

13

C NMR

Chemical Shifts, it have -164.3, 141.5, 135.5, 127.2, (alkene), 97.8 (aromatic) and 18.2
(alkanes). Then, for 1H NMR Chemical Shift, it have

-7.3 (aromatic), 6.0 and 4.7

(alkenes) and 2.0 (ketone / aldehyde / alkynes). In this compound, it consists of some
functional group include ester group, alkenes, and cycloalkane. In 1H NMR, for (1,t), it has
three peaks where it has carbon (contain one hydrogen) next to carbon that has two hydrogen.
18

For (2,s), it has one peaks where it has carbon (contain two hydrogen) next to carbon that has
no hydrogen. Then, for (2,d), it has two peaks where it has carbon (contain two hydrogen)
next to carbon that has one hydrogen. For (3,s), it has one peaks where it has carbon (contain
three hydrogen) next to carbon that has no hydrogen. It can see that (1H,t) has highest
chemical shift value because of electronegative element (O) lower the electron density around
the H and C.

Compound F

the IUPAC name for this compound is cyclobutylideneacetic acid

H NMR

O
HO

13

C NMR

O
HO

For compound F, the possible structure is cyclobutylideneacetic acid. From the

13

NMR Chemical Shifts, it has -193.0 (ketone / aldehyde), 104.3 (aromatic), 70.0 (ether
/alcohol), 32.3 (alkanes) and 21.1 (alkene / alkanes). Then, for 1H NMR Chemical Shift, it
have

-11.3 (carboxylic acid), 5.5 (alkenes), 2.5 and 2.4 (ketone / alkynes), and 2.0

(alkenes / alkynes / ketone). For this compound, it is a straight chain carbon. It consists of
several functional group include carboxyl acid, alkenes and alkanes. In 1H NMR, for 11.3
(1,s), it refers to hydroxyl group. It has highest chemical shift because located beside
electronegative element (O). Then, for 5.5 (1,s), it refers to the carbon that has one peak
where a carbon (contain one hydrogen) next to carbon that has no hydrogen. From the
19

compound, it can be seen at the alkenes group. For (2,t), it has three peaks where it has
carbon (contain two hydrogen) next to carbon that has two hydrogen and for (2,qnt), it
has five peaks where it has carbon (contain two hydrogen) next to carbon that has four
hydrogen.

Compound G

the IUPAC name for this compound is (5-methylfuran-2-yl) methanol

H NMR

H3C

O
OH

13

C NMR

H3C

O
OH

For compound G, the possible structure is (5-methylfuran-2-yl) methanol .From the


1

H NMR and 13C NMR data given, we know that this compound has 6 peaks for carbon, C

and 5 peaks for hydrogen, H. The chemical shifts data for

13

C NMR that given to us is

152.6, 152.1, 108.6, 106.3, 57.1 and 13.5. From the value given, we can identify the
functional group for the compound. From the data, 152.6 and 152.1 must be neighboring
carbon, and by referring to the 13C NMR chemical shifts table, the possible functional group
at these values is alkene (double bond). 108.6 and 106 also came from the neighboring
carbon as their values are very close and the possible functional group at these values is also
20

alkene. For 57.1, the possible functional group is ether or alcohol. Whereas, for 13.5 is
saturated alkanes. The chemical shifts data for 1H NMR given is 5.9(1,d), 6.1(1,d), 4.5(2,s),
2.3(1,s) and 2.3(3,s). By referring to the 1H NMR chemical shifts table, the possible
functional group for 5.9(1,d) and 6.1(1,d) is alkene, for 4.5(2,s) is alcohol, esters or alkene.
Lastly, for 2.3 is alcohol, ketones or alkyne (triple bond). By comparing the information
gained from both table, the similarities of the functional group they have is alkene and
alcohol, which means this compound must have this functional group. Besides these 2
functional groups, we need one more functional group to complete the structure that has 2
oxygen atoms, so the most possible functional group is ether.
Compound H
en-1-one

the IUPAC name for this compound is 2-hydroxy-3-methylcyclopent-2-

H NMR

O
HO

H3C

13

C NMR

O
HO

H3C
For compound H, the possible structure is 2-hydroxy-3-methylcyclopent-2-en-1-one.
From the 1H NMR and 13C NMR data given, we know that this compound has 6 peaks for
carbon, C and 4 peaks for hydrogen, H. The chemical shifts data for 13C NMR that given to us
is 203.8, 149.5, 145.9, 32.1, 27.3 and 14.4. From the value given, we can identify the
functional group for the compound. From the data, 149.5 and 145.9 must be neighboring
carbon, and by referring to the 13C NMR chemical shifts table, the possible functional group
at these values is alkene (double bond system). 32.1 and 27.3 also came from the
21

neighboring carbon as their values are very close and the possible functional group at these
values is ketones, saturated alkane or alkene. For 203.8, the possible functional group is
ketones or aldehydes. Whereas, for 14.4 is saturated alkanes. The chemical shifts data for 1H
NMR given is 2.0(3,s), 2.4(2,t), 6.7(1,s) and 2.3(2,t). By referring to the 1H NMR chemical
shifts table, the possible functional group for 2.4, 2.3, 2.0 is alcohol, ketones or alkene, for
6.4 is alkene. By comparing the information gained from both table, the similarities of the
functional group they have is alkene, saturated alkanes or ketones which means this
compound must have this functional group. Besides these functional groups, we need one
more functional group to complete the structure that has 2 oxygen atoms, so the most possible
functional group is alcohol.
Compound I

the IUPAC name for this compound is hex-2-ynoic acid

H NMR

O
CH3

HO

13

C NMR

O
CH3

HO

From the 1H NMR and 13C NMR data given, we know that this compound has 6 peaks
for carbon, C and 4 peaks for hydrogen, H. The chemical shifts data for 13C NMR that given
to us is 158.5, 92.6, 72.9, 21.0, 20.7 and 13.4. From the value given, we can identify the
functional group for the compound. From the data, 21.0 and 20.7 must be neighboring
carbon, and by referring to the 13C NMR chemical shifts table, the possible functional group
at these values is alkene (double bond system) or saturated alkanes. For 158.5, the possible
functional group is carboxylic acid. For 92.6 is ether or alcohol. For 72.9, the possible
functional group is alcohol, ether, or alkyl (triple bond system).Whereas, 13.4 is alkene and
saturated alkane. The chemical shifts data for 1H NMR given is 9.7(1,s), 2.3(2,t), 1.6(2,sxt)
22

and 1.0(3,t). By referring to the 1H NMR chemical shifts table, the possible functional group
for 2.3 and 1.6 is alcohol, ketones and alkyl, for 9.7 is ketones and for 1.0 is saturated
alkane. By comparing the information gained from both table, the similarities of the
functional group they have is saturated alkanes, alcohol, ketones and alkyl group. But instead
of alcohol and ketones group, the carboxylic acid is the most accurate to construct this
structure.

CONCLUSION

The experiment were successfully conducted where the entire unknown compound
were determined. From the analysis and investigation that have been done, it shows that the
IUPAC name for compound A to I are 2, 4-dimethylfuran-3(2H)-one, 2-methylcyclopentane1,3-dione,

cyclohexane-1,4-dione,

ethenyl

(2E)-but-2-enoate,

2-methylprop-2-enoate,

cyclobutylideneacetic acid, (5-methylfuran-2-yl) methanol, 2-hydroxy-3-methylcyclopent-2en-1-one, and hex-2-ynoic acid respectively.


The compound can be determined by analyses the peak and the chemical shifts shown
in the NMR spectrum. The splitting number of peak was known by looking at the proton
presents near the single carbon. Let say there are two neighboring hydrogen present at the
carbon, the number of peaks will be triplet.
Determining the chemical shifts of every structure of compound part is very important
as to know the compound. Chemical shifts are the frequency of a resonance signal influenced
by if the compound is shielded or deshielded. The shielding effect in H-NMR is influenced
by factors such as inductive effects by electronegative groups, magnet anisotropy, and
hydrogen bonding. From all these knowledge, it explains why the compounds A to I were
determined to be the compound that have been mentioned above. In conclusion, the
experiment was successfully conducted and the objectives were achieved.

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REFERENCE

Books
1. Graham S., Craig B., (2007).Organic chemistry.( 9th edition): John Wiley & Son
2. Laboratory Manual CHE 515,Faculty of Chemical Engineering
3. Notes NMR spectroscopy, Faculty of Chemical Engineering

Internet

1. Nuclear Magnetic Resonance, Instrumentalion December 11, 2012. Retrieve from


http://teaching.shu.ac.uk/hwb/chemistry/tutorials/molspec/nmr3.htm

2. Nuclear Magnetic Resonance (NMR) Spectroscopy. December 10, 2012. Retrieve


from http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch13/ch13-nmr-1.html

3. Nuclear Magnetic Resonance Spectroscopy. December 10, 2012. Retrieve from


http://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/Spectrpy/nmr/nmr1.htm

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