Chapter - 7

Nuclear Magnetic Resonance Spectroscopy

(NMR)

1
 Introduction
NMR is one of the most powerful techniques available for
studying the structure of molecules.

The NMR technique has developed very rapidly since the first
commercial instrument with small magnets installed in 1952 at
the Humble Oil Company in Baytown, Texas.

For studying protons (1H) in organic compounds, but only in

solution with high concentration of analyte or as neat liquids.

NMR instruments and experimental methods are now available

that permit the determination of the 3D structure of proteins as
large as 900,000 Da.

2
 NMR instruments coupled to liquid chromatographs and mass
spectrometers for separation and characterization of unknowns
are commercially available.

 NMR involves the absorption of radio waves by the nuclei of

some combined atoms in a molecule that is located in a
magnetic field.

When low energy radio waves interact with a molecule, they

can change the nuclear spins of some elements.

NMR can be considered a type of absorption spectroscopy, not

unlike UV/VIS absorption spectroscopy.

Radio waves are low energy electromagnetic radiation. Their

frequency is on the order of 107 Hz.
3
In analytical chemistry, NMR is a technique that enables us to
study the shape and structure of molecules.
If we already know what types of compounds are present, NMR
can provide a means of determining how much of each is in the
mixture.
It is thus a method for both qualitative and quantitative
analyses, particularly of organic compounds.
In addition, NMR is used to study chemical equilibria, reaction
kinetics, the motion of molecules, and intermolecular
interactions.

4
Structure determination of almost any organic or biological
molecule, as well as that of many inorganic molecules, begins
with nuclear magnetic resonance (NMR) spectroscopy.

 NMR allows characterization of a very small amount of sample

(2mg), and does not destroy the sample (non destructive
technique)
 Modern instruments with detection limits are approaching
nano gram levels.
Two common types of NMR spectroscopy are used to
characterize organic structure:
 1H NMR is used to determine the type and number of “H”
atoms in a molecule;
 13C NMR is used to determine the type of carbon atoms in the
molecule.
5
 Basic Principles of Nuclear Magnetic Resonance
Spectroscopy (NMRs)

NMR spectroscopy is based on the measurement of absorption

of electromagnetic radiation in the radio-frequency region of
roughly 4 to 900 MHz, which have long wavelengths, and thus
low energy and frequency.
When the nuclei of certain atoms are immersed in a static strong
magnetic field and exposed to a second oscillating magnetic field
in the form of radiofrequency pulses, it is possible to transfer
energy into the spin system and change the state of the system.

6
 Nuclei of atoms rather than outer electrons are involved in the
absorption process.
 When low-energy radio waves interact with a molecule, they
can change the nuclear spins of some elements.

 After the excitation, the system relaxes back to its state of

equilibrium, sending a weak signal that can be recorded.
 The theory behind NMR comes from the spin of the nucleus
and it generates a magnetic field.
When a charged particle such as a proton spins on its axis, it
creates a magnetic field.
Thus, the nucleus can be considered to be a tiny bar magnet.

7
 =>
Normally, these tiny bar magnets are randomly oriented in
space. However, in the presence of a magnetic field B0, they
are oriented with or against this applied field.
More nuclei are oriented with the applied field because this
arrangement is lower in energy.
In a magnetic field, there are now two energy states for a
proton: a lower energy state with the nucleus aligned in the
same direction as B0, and a higher energy state in which the
nucleus aligned against B0.
8
The distribution of
nuclear spins is +
random in the
absence of an
external magnetic
field. +

+
+

9
An external magnetic field
causes nuclear magnetic +
moments to align parallel
and antiparallel to applied
field. +

+
H0

+
+

10
There is a slight
excess of nuclear +
magnetic moments
aligned parallel to the
applied field.
+

+
H0

+
+

11
 • Imagine a charge travelling circularly about
an axis builds up a magnetic moment
• It rotates (spins) about its own axis (the blue
arrow) and precesses about the axis of the
magnetic field B (the red arrow). The
frequency of the precession () is
proportional to the strength of the magnetic
field:
 =  B0
 = gyromagnetic ratio
Magnetic field measured in Tesla
1 T = 10,000 gauss
• The larger the value of the magnetogyric ratio,
the larger the Magnetic moment (m) of the
nucleus and the easier it is to see by NMR
spectroscopy.
12
• Precession: The circular movement of the magnetic
moment in the presence of the applied field.
• Larmour frequency : The angular frequency of the
precession is related to the external magnetic field
strength B0, by the gyromagnetic ratio  :
0 = B0

13
For a proton, 1H, in an applied 2.35T magnetic field, the
precession frequency is 100 MHz. In the same externally applied
field, other nuclei that have different gyromagnetic ratios,
e.g., 13C and 19F, will precess at characteristically different
frequencies.

 In a 2.35 T magnetic field, 13C and 19F nuclei will precess at 25

and 94 MHz, respectively.

 This characteristic precession frequency is known as the Larmor

frequency of the nucleus.

14
 Precession or Larmor frequency:  = 2pn  o =  Bo (radians)

angular momentum (l)

l o m

Bo

Simply, the nuclei spins about its

axis creating a magnetic moment m Apply a large external field (Bo)
and m will precess about Bo at its
Maxwell: Magnetic field ≡ Moving charge Larmor () frequency.

Important: This is the same frequency obtained from the energy

transition between quantum states 15
 When an external energy source (hn) that matches the energy
difference (E) between two states is applied, energy is
absorbed, causing the nucleus to “spin flip” from one
orientation to another.

16
17
When this spin-flip occurs, the magnetic nuclei are said to be in
resonance with the applied radio frequency radiation (RF), hence
the name nuclear magnetic resonance.

Thus, two variables characterize NMR: an applied magnetic field

B0, the strength of which is measured in tesla (T), and the
frequency n of radiation used for resonance, measured in hertz
(Hz), or megahertz (MHz) i.e. (1 MHz = 106 Hz).

18
• Energy difference is proportional to the
magnetic field strength.
• E = hn =  h B0
2p
• Gyromagnetic ratio, , is a constant for each
nucleus (26,753 s-1gauss-1 for H).
• In a 14,092 gauss field, a 60 MHz photon is
required to flip a proton.

19
• The frequency needed for resonance and the applied
magnetic field strength are proportionally related:

21
22
 Properties of Nuclei
• To understand the properties of certain nuclei in an NMR experiment, we
must assume that nuclei rotate about an axis and therefore have a nuclear
spin, represented as I, the spin quantum number.
• In addition, nuclei are charged.
• The spinning of a charged body produces a magnetic moment along the axis
of rotation.
• For a nucleus to give a signal in an NMR experiment, it must have a nonzero
spin quantum number and must have a magnetic dipole moment.

• The spin quantum number I is a physical property of the nucleus, which is

made up of protons and neutrons.
• From observations of the nuclear spins of known nuclei, some empirical
rules for predicting the spin quantum numbers can be tabulated.

23
Table 1: Rules Predicting Spin Numbers of Nuclei
Mass (P + N) Charge (P) (atomic Spin quantum
(atomic weight) number) number (I)
Odd Odd or even 1/2, 3/2, 5/2, . . .
Even Even 0
Even Odd 1, 2, 3

24
 Nuclear Spin States (number of orientations)
 Any atomic nucleus that has an odd mass, an odd atomic
number, or both also has a spin and a resulting nuclear
magnetic moment.
 The allowed nuclear spin states are determined by the
spin quantum number, I , of the nucleus.
 A nucleus with spin quantum number I has 2I +1 spin
states.
 If I = 1/2, there are two allowed spin states.
 The permitted values for the magnetic quantum states,
symbolized by the magnetic quantum number, m = I, I-1, I-
2, . . . , -I
In the case of 1H, I = 1/2; hence the number of orientations
is 2(1/2) + 1 = 2.
 Consequently, for 1H only two energy levels are
permitted, one with m = +1/2 and the other with m = -
1/2.
25
For example, 12C has atomic weight 12 and atomic
number 6.

Hence it has 6 protons (atomic number = 6) and 6

neutrons (atomic weight – atomic number = No. of
neutrons, so 12 - 6 = 6 neutrons).

Since the mass and the number of protons are both

even numbers, the above table predicts that the net
spin quantum number of 12C is zero, denoting no spin.

26
Therefore, the spin angular momentum is zero and 12C does not
possess a magnetic moment.
Nuclei with I = 0 do not absorb RF radiation when placed in a
magnetic field and therefore do not give an NMR signal.
NMR cannot measure 12C, 16O, or any other nucleus with both an
even atomic mass and an even atomic number.
For 13C, on the other hand, the atomic weight is 13 (i.e., P + N =
13), an odd number and the atomic number is 6, an even
number. From Table 1, we predict that I for 13C is therefore a half
integer; like 1H, 13C has I = 1/2.
So NMR can detect 13C.

27
 Out of most abundant isotopes of common elements, NMR
notably measure those of C, O, Si, and S, which are very important
components of many organic molecules of interest in biology,
pharmaceutical industry, polymer industry, and chemical
manufacturing industry.

 The two nuclei of most importance to organic chemists and

biochemists, 1H and 13C, both have a spin quantum number = 1/2.

28
Instrumentation for NMR

29
Fig. Schematic of an NMR spectrometer
Components of an NMR spectrometer are :
1. powerful magnet that supply range of magnetic fields variable by
sweep generator.
2. a radio-frequency generator or transmitter
3. a radio-frequency receiver
4. a radio-frequency detector and
5. a sample holder 30
31
 An NMR spectrometer: the sample is dissolved in a solvent
usually CDCl3 (deutrochloroform), and placed in a magnetic
field.
 A radiofrequency generator then irradiates the sample with a
short pulse of radiation, causing resonance.
 When the nuclei fall back to their lower energy state, the
detector measures the energy released, and a spectrum is
recorded.

 The decaying signal recorded by the receiver coil is processed

through an analog-to-digital converter (ADC) and stored in
memory.
32
33
An NMR Laboratory

34
Types of NMR Spectra
 Most NMR spectra can be categorized as either wide line or high
resolution.

A. Wide-Line spectra: Wide-line spectra are those in which the

bandwidth of the source of the lines is large enough so that the
fine structure due to chemical environment is obscured.

• A single peak is associated with each species.

35
FIG. A low-resolution NMR spectrum of water in a glass
container. Frequency ~ 5 MHz.

36
A single resonance is associated with each species.

Wide-line spectra are useful for the quantitative

determination of isotopes and for studies of the physical
environment of the absorbing species.

Wide-line spectra are usually obtained at relatively low

magnetic field strength.

37
B. High-Resolution Spectra:
Most NMR spectra are high resolution and are collected by
instruments capable of differentiating between very small
frequency differences of 0.01 ppm or less.

 In the lower-resolution spectrum for the protons in ethanol,

three peaks are observed arising from absorption by the CH3,
CH2, and OH protons.

 But in the higher resolution spectrum, two of the three peaks can
be resolved into additional peaks.

38
B. High-Resolution Spectra: Most NMR spectra are high resolution
and are collected by instruments capable of differentiating
between very small frequency differences of 0.01 ppm or less.

 In the lower-resolution spectrum for the protons in ethanol,

three peaks are observed arising from absorption by the CH3,
CH2, and OH protons.

 But in the higher resolution spectrum, two of the three peaks can
be resolved into additional peaks.

39
 Environmental effects on NMR spectra

• The frequency of Radio Frequency (RF) radiation that is

absorbed by a given nucleus is strongly affected by its chemical
environment :

• That is, by nearby electrons and nuclei.

• As a consequence, even simple molecules provide a wealth of

spectral information that can serve to elucidate their chemical
structure.

40
 Types of Environmental Effects
Shielding
An external magnetic field
affects the motion of the
electrons in a molecule,
inducing a magnetic field
within the molecule. C H

 The direction of the induced

magnetic field is opposite to
that of the applied field.
H0

41
 The induced field shields the nuclei (in this case, 13C

and 1H) from the applied field.

 A stronger external field is needed in order for energy
difference between spin states to match energy of
radio frequency radiation.

Shielding: influence of neighboring functional groups on the

electronic structure around a nuclei and consequently the
chemical shift of their resonance.

42
Chemical shift: In the NMR experiment, nuclei in
different chemical environments within a molecule
absorb at slightly different frequencies.

This variation in absorption frequency is caused by a

slight difference in the electronic environment of the
nuclei as a result of different chemical bonds and
adjacent atoms.

43
The absorption frequency for a given nuclei depends on
the chemical structure of the molecule.

This variation in absorption frequency is called the

chemical shift.

An NMR spectrum is a plot of the intensity of a peak

against its chemical shift, measured in parts per million
(ppm).
44
 Chemical shift is a measure of
the degree to which a nucleus in
C H
a molecule is shielded.
 Protons in different
environments are shielded to
greater or lesser degrees; they H0
have different chemical shifts.

 The numerical value of the chemical shift for nuclei gives a clue
as to the type of nuclei originating the signal, just as infrared
frequency gives a clue as to the type of bond or functional
group.

45
 Downfield Upfield
Decreased shielding Increased shielding

(CH3)4Si (TMS)

10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0
H0
Chemical shift (d, ppm)
measured relative to TMS
46
Spin-Spin Splitting:
 The splitting of chemical shift peaks occurs as the
magnetic moment of a nucleus interacts with the
magnetic moments of immediately adjacent nuclei.
The magnetic field created by a spinning nucleus
affects the distribution of electrons in its bonds
to other nuclei.
 This change in electron distribution then produces
changes in the magnetic field of adjacent nuclei and
causes splitting of energy levels and hence multiple
transitions.

47
 1H NMR SPECTROSCOPY

• The number of NMR signals equals the number of different

types of protons in a compound.
• Protons in different environments give different NMR signals.
• Equivalent protons give the same NMR signal.

48
 NMR absorptions generally appear as sharp peaks.
 Increasing chemical shift is plotted from right to left.
 Most protons absorb between 0-10 ppm.
 NMR absorptions are measured relative to the position of a
reference peak at 0 ppm on the d (chemical shift) scale due to
tetramethylsilane (TMS).
 The chemical shift of the x axis gives the position of an NMR
signal, measured in ppm, according to the following equation:

49
where ʋS is the resonant frequency of a specific nucleus; ʋR, the
resonant frequency of the reference nucleus; and ʋNMR, the
spectrometer frequency.

50
 1H NMR—Position of Signals
 In the vicinity of the nucleus, the magnetic field
generated by the circulating electron decreases the
external magnetic field that the proton “feels”.
The less shielded (deshielded) the nucleus becomes, the
more of the applied magnetic field (B0) it feels.
 This deshielded nucleus experiences a higher magnetic field
strength, so, it needs a higher frequency to achieve resonance.
 Higher frequency is to the left in an NMR spectrum, toward
higher chemical shift—so deshielding shifts an absorption
downfield.
51
 Protons near electronegative atoms are deshielded, so they
absorb downfield.

 The more shielded (shielded) the nucleus becomes, the less the
applied magnetic field (B0) it feels.
 This shielded nucleus experiences a lower magnetic field
strength, so, it needs a lower frequency to achieve resonance.

 Lower frequency is to the right in an NMR spectrum, toward

lower chemical shift—so shielding shifts an absorption upfield.

52
52
53
53
54
 1H NMR—Chemical Shift Values
• Protons in a given environment absorb in a predictable region in an NMR
spectrum.

55
 Calculating 1H NMR—Chemical Shift Values

• The chemical shift of a C—H can be calculated with a high degree

of precision if a chemical shift additivity table is used.

• The additivity tables starts with a base chemical shift value

depending on the structural type of hydrogen under
consideration:

Methylene Methine

CH3 C C
H2 H
Base Chemical Shift 0.87 ppm 1.20 ppm 1.20 ppm

56
56
 Calculating 1H NMR—Chemical Shift Values

• The presence of nearby atoms or groups will effect the base

chemical shift by a specific amount:
• The carbon atom bonded to the hydrogen(s) under consideration
are described as alpha () carbons.
• Atoms or groups bonded to the same carbon as the hydrogen(s)
under consideration are described as alpha () substituents.
• Atoms or groups on carbons one bond moved from the  carbon
are called beta () carbons.
• Atoms or groups bonded to the  carbon are described as beta
() substituents.

 

C C H (Hydrogen under consideration)

57
57
Calculating 1H NMR—Chemical Shift Values

 
H H
Cl C C H (Hydrogen under consideration)
H H Base Chemical Shift = 0.87 ppm
no  substituents = 0.00
one  -Cl (CH3) = 0.63
TOTAL = 1.50 ppm

 
H H
Cl C C H (Hydrogen under consideration)
H H Base Chemical Shift = 1.20 ppm
one  -Cl (CH2) = 2.30
no  substituents = 0.00
TOTAL = 3.50 ppm

58
58
1H NMR of Methyl Acetate

Base Chemical Shift = 0.87 ppm

O
one  R C O = 2.88 ppm
TOTAL = 3.75 ppm
O

H3C C O CH3

Base Chemical Shift = 0.87 ppm

O
one  C R = 1.23 ppm
59
TOTAL = 2.10 ppm
 2,3-Dimethyl-2-Butene

(Hydrogen under consideration)

Base Chemical Shift = 0.87 ppm
one H2C C
H
(CH3) = 0.78 ppm
TOTAL = 1.65 ppm
60
1H NMR—Chemical Shift Values
• In a magnetic field, the six p electrons in benzene circulate around the ring
creating a ring current.
• The magnetic field induced by these moving electrons reinforces the
applied magnetic field in the vicinity of the protons.
• The protons thus feel a stronger magnetic field and a higher frequency is
needed for resonance. Thus they are deshielded and absorb downfield.

61
61
• In a magnetic field, the p electrons of a carbon-carbon triple bond are
induced to circulate, but in this case the induced magnetic field opposes
the applied magnetic field (B0).

• Thus, the proton feels a weaker magnetic field, so a lower frequency is

needed for resonance. The nucleus is shielded and the absorption is
upfield.

62
 Nuclear Magnetic Resonance Spectroscopy
1H NMR—Chemical Shift Values

63
64
65
 Spin-Spin Splitting in 1H NMR Spectra

 Peaks are often split into multiple peaks due to magnetic interactions
between nonequivalent protons on adjacent carbons, the process is called
spin-spin splitting.
 The splitting is into one more peak than the number of H’s on the adjacent
carbon(s), This is the “n+1 rule”.

 It is important to remember that spin–spin splitting by a given nucleus

causes a change in the fine structure of peak for the adjacent protons in the
molecule.
 For example, CH3CH2CH2CHO the CH2 splits the H of the adjacent CHO group,
and the H of the CHO group splits the adjacent CH2, but the CH2 does not
split itself because that interaction is forbidden by quantum theory.

66
67
67
Four general rules describe the splitting patterns commonly
seen in the 1H NMR spectra of organic compounds.

1. Equivalent protons do not split each other

2. A set of n nonequivalent protons splits the signal of a nearby

proton into n + 1 peaks.

3. Splitting is observed for nonequivalent protons on adjacent

carbons.
68
 If Ha and Hb are not equivalent, splitting is observed.

4. Splitting is not generally observed between protons separated by

more than three  bonds.
 Number of peaks = number of chemically different H’s on adjacent atoms + 1

0 neighbouring H’s signal isn’t split 1 peak “singlet”

1 neighbouring H signal split into 2 peaks “doublet” ratio = 1:1
2 neighbouring H’s 3 peaks “triplet” 1:2:1
3 neighbouring H’s 4 peaks “quartet” 1:3:3:1
4 neighbouring H’s 5 peaks “quintet” 1:4:6:4:1

PASCAL’S TRIANGLE

It is interesting to note the relationship between

the successive peak ratios.
It follows the pattern found in Pascal’s triangle.
1
Each number in the series is the sum of the two 1 1
numbers above it in the triangle 1 2 1
1 3
1 3
What would be the pattern for 6 neighbouring 1 4 6 4 1
hydrogens? 1 5 10 10 5 1
1 6 15 20 15 6 1

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73
Example 1.
The structure of 1,1-dichloroethane is:

 The single proton on the carbon containing the two Cl atoms will
be split into (3 + 1) peaks by the three equivalent protons on the
adjacent methyl group.
 The multiplicity of this peak is 4 and it is called a quartet.
 Each peak in the quartet will be separated by exactly the same
frequency; they will be evenly spaced. The relative peak
intensities will be 1:3:3:1.

74
 The peak due to the three methyl protons will be split into (1 +
1) peaks, a doublet with a multiplicity of 2, by the adjacent
single proton.

 The spacing between the two peaks in the doublet will be

exactly the same as the peak spacing in the quartet and the
ratio of peak intensities in the doublet will be 1:1.

75
Example 2:
For each of the following compounds, calculate the number of
multiplets for each band and their relative areas:

(a) Cl(CH2)3Cl (b) CH3CH2OCH3

Solutions:

(a)The multiplicity associated with the four equivalent protons on

the two ends of the molecule is determined by the number of
protons on the central carbon; thus, the multiplicity is 2 + 1 = 3
and the areas have the ratio 1:2:l.

76
 The multiplicity of the central methylene: protons is
determined by the four equivalent protons at the ends and is 4
+ 1 = 5.
 Expansion of (x+1)4 gives the coefficients which are
proportional to the areas of the peaks 1:4:6:4:1.
(b) The right methyl protons are separated from the others by
more than three bonds so that only a single peak is observed.
The protons of the central methylene group have a multiplicity
of 3 + 1 = 4 and a ratio of 1:3:3:1.
 The left methyl protons have a multiplicity of 2 + 1 = 3 and an
area ratio of 1:2:1.

77
 Rules Governing the Interpretation
The following rules govern the appearance of spectra on 1H–NMR .

 Equivalent nuclei do not interact with one another to give

multiple absorption peaks.

 The multiplicity of a band is determined by the number n of

magnetically equivalent protons on the neighboring atoms
and is given by the quantity n + 1.
The type of proton environment can be identified by looking
up the chemical shift in a correlation table (data book).
The area under the peak relates to the number of protons in
the environment.
78
Four different features of a 1H NMR spectrum provide
information about a compound’s structure:

a. Number of signals

b. Position of signals

c. Intensity of signals

d. Spin-spin splitting of signals

79
Application of 1H -NMR

 The most important chemical applications of 1H–NMR

spectroscopy have been to the identification and structural

elucidation of organic, metal-organic, and biochemical molecules.
In addition, however, the method is often useful for quantitative
determination of absorbing species.

80
1. Number of proton determination

81
81
2. Structural determination

82
83
84
85
 13C NMR SPECTROSCOPY
 13C Spectra are easier to analyze than 1H spectra because the
signals are not split.

Each type of carbon atom appears as a single peak.

86
87
13C NMR-Number of Signals
The number of signals in a 13C spectrum gives the number of
different types of carbon atoms in a molecule.
 Because 13C NMR signals are not split, the number of signals
equals the number of lines in the 13C spectrum.
 In contrast to the 1H NMR situation, peak intensity is not
proportional to the number of absorbing carbons, so 13C NMR
signals are not integrated.

88
 13C NMR—Position of Signals
In contrast to the small range of chemical shifts in 1H NMR (1-10
ppm usually), 13C NMR absorptions occur over a much broader
range (0-220 ppm).

 The chemical shifts of carbon atoms in 13C NMR depend on the

same effects as the chemical shifts of protons in 1H NMR.

89
1. Provides a count of the d/t environments of C- atoms
in a molecule 13C resonances are 0 to 220 ppm
downfield from TMS.
2. Chemical shift affected by electro negativity of
nearby atom O, N, halogen decrease electron density
and “deshield”, moving signal downfield.
3. sp3 C signal is at d 0 to 9; sp2 C: d 110 to 220 C(=O) at
the down field, d 160 to 220.

90
 Nuclear Magnetic Resonance Spectroscopy

Fig. Chemical shifts for 13C using TMS as the 0.0 ppm reference.
The abbreviation Hal stands for halogen, (i.e., Cl, Br, or I.)
92
93
Isomers H H H H Br H
of C3H7Br
HCCCBr HCCCH

H H H H H H

3 peaks 2 peaks
all three carbons are different the two outer carbons are similar

Ethanol H H

COH HC
C2H5OH H H
This is where the
H H proton nmr
H  C  C  OH spectrum of ethanol
would be on the
H H same scale.

94
The carbon-13 spectrum of 2-methylbutane (CH3)2CHCH2CH3

chemically
equivalent There are four
carbon atoms chemically different
H CH3 H H
carbon atoms in the
HCCCCH molecule so there
are four peaks in the
H H H H
C-13 nmr spectrum.

NO SPLITTING WITH C-13

ONLY ONE PEAK FOR
EACH CARBON

Other isomers of C5H12

pentane CH3CH2CH2CH2CH3 3 peaks
2,3-dimethylpropane (CH3)4C 2 peaks
95
 QUESTIONS

1. How many peaks would you expect there to be in the carbon-13

spectrum of…

• butane CH3CH2CH2CH3
• 2-methylpropane CH3CH(CH3)CH3
• butanal CH3CH2CH2CHO
• butanone CH3COCH2CH3
• pentan-2-one CH3COCH2CH2CH3
• pentan-3-one CH3CH2COCH2CH3
• cyclohexane C6H12

96
2. Identify the isomers of C4H8O

97
3. Identify the isomers of C6H12

98
Advantages Carbon-13 NMR over proton NMR
 Have a better power to elucidate organic and biochemical
structures.

 In addition, the chemical shift range for 13C, for most organic
compounds is about 200 ppm, compared with 10 to 15 ppm for
the proton. As a result, there is less spectral overlap in 13C spectra
than in proton spectra.

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Application of 13C NMR
 As with proton NMR, the most important and widespread

 applications of 13C NMR are for the determination of

structures of organic and biochemical species.

 Such determinations are based largely on chemical shifts, with

spin-spin data playing a lesser role.

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THE END!
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