CHM557

ORGANIC CHEMISTRY
CHAPTER 3
SPECTROSCOPY OF
CARBON
COMPOUNDS
 At the end of the chapter,
student should be able to
understand

COURSE ► Introduction to spectroscopy

LESSON and structural identification
► Infrared spectroscopy
PLAN ► Proton Nuclear Magnetic
Resonance Spectroscopy
► Carbon-13 Nuclear Magnetic
Resonance Spectroscopy
 INTRODUCTION TO
SPECTROSCOPY AND
STRUCTURAL
IDENTIFICATION
• Spectroscopy is an analytical technique which helps
determine structure.

• It destroys little or no sample.

• Spectroscopy: The study of the interaction between

ELECTROMAGNETIC (EM) RADIATION and MATTER.
- Example of interactions: Absorption, emission,
scattering, etc
- Types of EM: gamma ray, X-rays, Ultra-violet,
Visible, Infrared, Microwave and radio waves
- Matter: Sample analytes such as atom, molecules
and nuclei.
 ELECTROMAGNETIC SPECTRUM
• Electromagnetic radiation: Radiant energy that exhibits
wavelength-like behaviour and travels through space at
the speed of light in a vacuum.

• The important parameters associated with electromagnetic

radiation are:
✔ Energy (E): Energy is directly proportional to frequency, and
inversely proportional to wavelength, as indicated by the
equation below.

E = hν
h = Planck’s constant

✔ Frequency (ν)
✔ Wavelength (λ)
 Electromagnetic Spectrum
• Electromagnetic spectrum: The entire range and scope of
frequencies of electromagnetic radiation.

Types of EM:
gamma ray, X-rays,
Ultra-violet, Visible,
Infrared, Microwave
and radio waves
EFFECT OF ELECTROMAGNETIC RADIATION
ON MOLECULES

Graphics source: Wade, Jr., L.G. Organic Chemistry, 5th ed. Pearson Education Inc., 2003
• Wavenumbers (ῡ) is another way to describe frequency.
- most often used in IR
- The number of waves in 1 cm
- Unit: reciprocal of cm (cm-1)
- Scientists use wavenumber in preference to wavelength
because is directly proportional to Energy (E).

ῡ (cm-1 ) = 1 E = hc = hν = hcῡ
λ (cm) λ
 ORGANIC STRUCTURE DETERMINATION

How do we know:

• How atoms are connected together?

• Which bonds are single, double, or triple?
• What functional groups exist in the molecule?
• If we have a specific stereoisomer?

The field of organic structure determination attempts

to answer these questions.
 INSTRUMENTAL METHODS OF STRUCTURE
DETERMINATION
1. Nuclear Magnetic Resonance (NMR) – Excitation of the nucleus of
atoms through radiofrequency irradiation. Provides extensive
information about molecular structure and atom connectivity.

2. Infrared Spectroscopy (IR) – Triggering molecular vibrations

through irradiation with infrared light. Provides mostly information
about the presence or absence of certain functional groups.

3. Mass spectrometry – Bombardment of the sample with electrons

and detection of resulting molecular fragments. Provides information
about molecular mass and atom connectivity.

4. Ultraviolet spectroscopy (UV) – Promotion of electrons to higher

energy levels through irradiation of the molecule with ultraviolet
light. Provides mostly information about the presence of conjugated
π systems and the presence of double and triple bonds.
INFRARED SPECTROSCOPY
 IR spectral regions
Region Wavelengths Wavenumber, Frequency (υ), hz
(λ), μm cm-1
Near 0.78 to 2.5 12800 to 4000 3.8x1014 to 1.2x1014

Middle 2.5 to 50 400 to 200 1.2x1014 to 6.0x1012

Far 50 to 1000 200 to 10 6.0x1014 to 2.0x1011

Most 2.5 to 15 4000 to 670 1.3x1014 to 2.0x1013

used

Whereby:
Wavenumber = 1/wavelength
 Applications of
IR is to determine
• The main goal of IR spectroscopic analysis
the chemical functional groups in the sample.

• Example:
- Analysis of organic materials
- Polyatomic inorganic molecules
- Organometallic compounds

• Near IR - carbohydrates and proteins

• Middle IR - organic molecules

• Far IR - inorganic (co-ordination bonds & quaternary

ammonium compounds)
 MOLECULAR VIBRATIONS
• Covalent bonds vibrate at only certain allowable frequencies.
• Imagine a covalent bond between two atoms acts like a spring.
- If the bond is stretched, a restoring force pulls the two atoms together
towards equilibrium bond length.
- If the bond is compressed, the restoring force pushed the two atoms
apart.
- if the bond is stretched or compressed and then released, the atoms
vibrate.

Graphics source: Wade, Jr., L.G. Organic Chemistry, 5th ed. Pearson Education Inc., 2003
 MOLECULAR
VIBRATIONS

STRECTHING BENDING

IN-PLANE IN-PLANE
SYMMETRIC ASYMMETRIC
ROCKING SCISSORING

OUT-OF-PLANE OUT-OF-PLANE
WAGGING TWISTING
A) STRETCHING VIBRATIONS:
• A continuous change in the interatomic distance along the axis of the
bands between the two atoms.
• The most useful bands in an infrared spectrum correspond to stretching
frequencies
• Causes by vibration of the bond length.
• Two vibrational stretching modes:
i) symmetric stretching
ii) asymmetric stretching

Symmetric stretching Asymmetric stretching

 Stretching Frequencies
• Frequency decreases with increasing atomic weight.
- heavier atoms vibrate more slowly than lighter atoms.
- example: C-D bond had lower frequency than a C-H bond.
• Frequency increases with increasing bond energy.
- stronger bonds are stiffer, requiring more force to stretch or
compress.
- stronger bands usually vibrate faster than weaker bands (assuming
the atoms have similar masses)
- example: O-H bonds are stronger than C-H bonds and O-H bonds
vibrate at higher frequencies.
- strengthens of bonds: triple bonds > double bonds > single
bonds

Specific bonds respond to (absorb) specific frequencies

Bond Stretching Frequencies
B) BENDING VIBRATIONS:

- causes by the vibration of the bond angles.

- four bending vibrations modes:
i) in-plane rocking
ii) in-plane scissoring
iii) out-of-plane wagging
iv) out-of-plane twisting
 Bending
Vibrations
Modes
 MOLECULAR SPECIES THAT ABSORB INFRARED
o
RADIATION
IR absorption only occurs when IR radiation interacts with a
molecule undergoing a change in dipole moment when the
molecule is vibrate.
o What happen when a molecule absorbs infrared radiation?
✔ Absorption of IR radiation corresponds to energy changes
on the order of 8 to 40 kJ/mole.
- Radiation in this energy range corresponds to stretching and
bending vibrational frequencies of the bonds in most
covalent molecules.
✔ In the absorption process, those frequencies of IR radiation
which match the natural vibrational frequencies of the
molecule are absorbed.
✔ The energy absorbed will increase the amplitude of the
vibrational motions of the bonds in the molecule.
• NOT ALL bonds in a molecule are capable of
absorbing IR energy. Only those bonds that
have change in dipole moment are capable to
absorb IR radiation.

• The larger the dipole change, the stronger

the intensity of the band in an IR spectrum.
MOLECULAR SPECIES THAT DO NOT ABSORB INFRARED
RADIATION
• A bond is symmetrical and has zero dipole moment.
- Example: the triple bond of acetylene, has zero dipole
moment, and dipole moment remains zero if the bond is
stretched or compressed. The vibration produces no change
in the dipole moment, thus no absorption of energy is
occurred.

- Examples: O2, N2, Cl2 cannot absorb IR radiation because no

net change in dipole moment occurs during the vibration or
rotation.
IR SPECTRA
 IR spectra

• Plot of %T vs. cm-1

• Linear wavenumber scale is preferred
• Direct proportionality between wavenumber and
both energy and frequency
Example: IR absorption spectrum of a polystyrene film

%Transmittance (%T) versus wavenumber (cm-1)

Example: IR absorption spectrum of a polystyrene
film

% Transmittance
show the value of IR
radiation being
absorbed by
molecule (functional
group)
- High %T = less IR
radiation (photon)
being absorbed
- Low %T = high IR
radiation (photon)
being absorbed
Wavenumber show the very particular energy
of IR
 Comparison between transmittance (upper) vs absorbance (lower) plot

Transmittance
spectra provide
better contrast
between
intensities of
strong and weak
, cm-1
bands compared
to absorbance
spectra
Absorption
 CLASSIFICATION OF IR BANDS
❑ IR bands can be classified as strong (s), medium (m), or weak (w),
depending on their relative intensities in the infrared spectrum.
❑ A strong band covers most of the y-axis.
❑ A medium band falls to about half of the y-axis
❑ A weak band falls to about one third or less of the y-axis.
 INFRARED ACTIVE BONDS
▪ Not all covalent bonds display bands in the IR spectrum. Only polar
bonds do so. These are referred to as IR active.
▪ The intensity of the bands depends on the magnitude of the dipole
moment.
▪ Strongly polar bonds such as carbonyl groups (C=O) produce
strong bands.
▪ Medium polarity bonds and asymmetric bonds produce medium
bands.
▪ Weakly polar bond and symmetric bonds produce weak or non
observable bands.
 INFRARED BAND SHAPES
• Infrared band shapes come in various forms. Two of the most
common are narrow and broad. Narrow bands are thin and
pointed, like a dagger. Broad bands are wide and smoother.

• A typical example of a broad band is that displayed by O-H bonds,

such as those found in alcohols and carboxylic acids, as shown
below.
INFORMATION OBTAINED FROM IR SPECTRA
• IR is most useful in providing information about the presence
or absence of specific functional groups.

• IR can provide a molecular fingerprint that can be used

when comparing samples. If two pure samples display the
same IR spectrum it can be argued that they are the same
compound.

• IR does not provide detailed information or proof of

molecular formula or structure. It provides information on
molecular fragments, specifically functional groups.

• Therefore it is very limited in scope, and must be used in

conjunction with other techniques to provide a more complete
picture of the molecular structure.
INTERPRETATION
OF IR SPECTRA
 IR ABSORPTION RANGE
The typical IR absorption range for covalent bonds is 600 - 4000 cm-1. The graph
shows the regions of the spectrum where the following types of bonds normally
absorb. For example a sharp band around 2200-2400 cm-1 would indicate the
possible presence of a C-N or a C-C triple bond.

Graphics source: Wade, Jr., L.G. Organic Chemistry, 5th ed. Pearson Education Inc., 2003
The approximately regions where various common types of bonds
absorb (stretching vibrations only; bending, twisting and other
types of bond vibrations have been omitted for clarity)
 THE FINGERPRINT REGION
• Although the entire IR spectrum can be used as a fingerprint for the purposes of
comparing molecules, the 600 - 1400 cm-1 range is called the fingerprint
region. This is normally a complex area showing many bands, frequently
overlapping each other. This complexity limits its use to that of a fingerprint, and
should be ignored by beginners when analyzing the spectrum.
• Focus the analysis on the rest of the spectrum, that is the region to the left of
1400 cm-1.

Focus your analysis on this region. This is where most Fingerprint region: complex and difficult to
stretching frequencies appear. interpret reliably.

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 FINGERPRINT OF MOLECULE
Whole-molecule vibrations and bending vibrations are also
quantized.
No two molecules will give exactly the same IR spectrum
(except enantiomers).
Simple stretching: 1600-3500 cm-1.
Complex vibrations: 600-1400 cm-1, called the “fingerprint
region.”
IR spectra is called “fingerprints” because no other chemical
species will have identical IR spectrum.
Significant of fingerprint region:
- The complex vibrations found in this region are used to confirm
the identity of an organic compound (since different compounds
cannot show the same vibrations).
 CORRELATION CHART

(1600-1585 cm-1 and 1500-1400 cm-1)

Intensities: s = strong, m = medium, w = weak, b = broad

 Type of vibration Frequency (cm-1) Intensity

Intensities: s = strong, m = medium, w = weak, b = broad

 Type of vibration Frequency (cm-1) Intensity

Intensities: s = strong, m = medium, w = weak, b = broad

IR SPECTRA OF CHEMICAL CLASSES OF
ORGANIC COMPOUND

1. IR spectrum of hydrocarbons
a) IR spectrum of alkanes
b) IR spectrum of alkenes
c) IR spectrum of alkynes
2. IR spectrum of aromatic compounds
3. IR spectrum of an alcohols
4. IR spectrum of amines
5. IR spectrum of aldehydes
6. IR spectrum of ketones
7. IR spectrum of carboxylic acids
8. IR spectrum of esters
9. IR spectrum of amides
10. IR spectrum of acid chlorides
11. IR spectrum of anhydrides
12. IR spectrum of a nitrile
 1. IR SPECTRUM OF HYDROCARBONS
Carbon-Carbon Bond Stretching

✔ Stronger bonds absorb at higher frequencies:

C-C 1200 cm-1
C=C 1660 cm-1
C≡C 2200 cm-1 (weak or absent if internal)

✔ Conjugation lowers the frequencies:

isolated C=C 1640-1680 cm-1
conjugated C=C 1620-1640 cm-1
aromatic C=C approx. 1600 cm-1
 Carbon-Hydrogen Stretching
✔ Bonds with more s character absorb at a higher frequency.
✔ Bonds are stronger in the order sp > sp2 > sp3
✔ Increase % s-character make the bond more stiffer thus
increase the energy (wavenumber)

Hybridization C-H bond s character Frequency (cm-1)

sp3 ¼ x 100 = 25% 2800-3000

sp2 1/3 x 100 = 33% 3000-3100

sp ½ x 100 = 50% ~ 3300

 a) IR SPECTRUM OF ALKANES
Alkanes have no functional groups. Their IR spectrum displays only C-C and C-H
bond vibrations. Of these the most useful are the C-H bands, which appear
around 3000 cm-1. Since most organic molecules have such bonds, most organic
molecules will display those bands in their spectrum.

C-C absorption is weak and

indistinguishable
 b)IR SPECTRUM OF ALKENES

• C=C absorbs at 1600-1700 cm-1 (stronger & stiffer than

C–C (μ = 0)
- sharp, medium bands
- useful for structure determination: unsymmetrical
absorption ~ 1600 – 1680 cm-1

• =C–H bond stretch at ~ 3020 – 3100 cm-1

• -C–H bond stretch at ~ 3000 – 2800 cm-1

 IR SPECTRUM OF 1-HEXENE

• C-H stretching corresponds to =C-H bonds involving sp2 hybrid C:

3080 cm-1
• Stretching C=C: 1642 cm-1
 c)IR SPECTRUM OF ALKYNES
• C≡C is stronger and stiffer than C–C and C=C
→ Absorb IR at higher ν ≈ 2100 – 2200 cm-1

~ 2100 – 2200 cm-1

sharp, weak band, Stretch very
moderate intensity weak or absent

Terminal alkyne Internal alkyne

IR SPECTRA OF 1-OCTYNE AND 4-OCTYNE

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 2.IR SPECTRUM OF AROMATIC COMPOUNDS

• =C-H stretch for sp2 hybrid: values greater than 3000 cm-1

• C=C ring stretch absorptions: occur in pairs at 1600-1585

cm-1 and 1500-1400 cm-1 (~1475 cm-1)

• =C-H bending: 900 - 690 cm-1

IR SPECTRUM OF TOLUENE
 3.IR SPECTRUM OF AN ALCOHOL
• The most prominent band in alcohols is due to the O-H bond
- Appears as a strong, broad band covering the range of about 3000 -
3700 cm-1.

• O–H stretching is broad due to the hydrogen bonding.

• Alcohol also show strong C–O stretching centered at ~1050 cm-1.

 IR SPECTRUM OF 1-BUTANOL

Broad, intense O-H stretching

absorption centered around
3300 cm-1
 4.IR SPECTRA OF AMINES
• The most characteristic band in amines is due to the N-H bond
stretch, and it appears as a weak to medium, somewhat broad band
(but not as broad as the O-H band of alcohols). This band is
positioned at the left end of the spectrum, in the range of about 3200 -
3600 cm-1.

• Primary amines (RNH2):

- have two N-H bonds
- two broad sharp spikes

• Secondary amines (R2NH2):

- have one N-H bond
- Broad, one sharp spike

• Tertiary amines (R3N):

- no N-H bonds
- No signal for NH bond
IR SPECTRUM OF 1-AMINOBUTANE (PRIMARY AMINE)

N-H
N-H bending
stretching
N-H oop
IR SPECTRUM OF DIETHYLAMINE (SECONDARY AMINE)

N-H oop
 IR SPECTRUM OF N,N-DIETHYL-1-BUTANAMINE
(TERTIARY AMINE)

CH2
bend
No signal for C-N stretch
NH bond at
3200 - 3600 CH3 bend
cm-1

C-H
stretch
 5. IR SPECTRUM OF ALDEHYDES

C=O stretch: ~ 1725 cm-1 (s).

Conjugation moves the absorption
to a lower frequency.

Two C-H stretching: ~ 2750 cm-1 and

2850 cm-1 (w)

C=O stretching: 1700-1660 cm-1

(conjugation of C=O with phenyl)

C=C aromatic: Two C-H stretching: ~ 2750 cm-1 and

1600,1450 cm-1 2850 cm-1 (w)
IR SPECTRUM OF BUTYRALDEHYDE

C-H aldehyde
C=O stretch

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 6. IR SPECTRUM OF KETONES

C=O stretching: ~1715 cm-1.

Conjugation moves the absorption to
a lower frequency.

C=O stretching: 1700-1680 cm-1

(Conjugation of C=O with phenyl)

C=C aromatic: 1600,

1450 cm-1
IR SPECTRUM OF 2-HEPTANONE

C=O stretch

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
IR SPECTRUM OF 2-BUTANONE
 7. IR SPECTRUM OF CARBOXYLIC ACIDS

C=O stretching: broad

(stake-shaped band), occurs at
1730-1700 cm-1. Conjugation
moves the absorption to a lower
frequency.

C-O stretching: O-H stretching: very broad (strongly

1320-1210 cm-1 hydrogen-bonding), occurs at
(medium intensity) 3400-2400 cm-1 and often overlaps
the C-H absorptions
 IR SPECTRUM OF HEXANOIC ACID

C-O stretch

This O-H absorbs broadly, 2500-3500

cm-1, due to strong hydrogen bonding

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 8. IR SPECTRUM OF ESTERS

C=O stretch: 1750-1735 cm-1 for normal

esters. Conjugation in R moves the
absorption to a lower frequency
(1740-1715 cm-1 ). Conjugation with O
in the R’ part moves the absorption to
a higher frequency.

C-O stretch: two or more bands,

one stronger and broader than the
other, occurs in the range
1300-1000 cm-1.
IR SPECTRUM OF ETHYL ACETATE
IR SPECTRUM OF ETHYL BENZOATE

C=O stretch: 1726 cm-1

(Conjugation in R moves
the absorption to a lower
frequency)
IR SPECTRUM OF VINYL ACETATE

C=O stretch: 1762 cm-1 (Conjugation

with O in the R’ part moves the
absorption to a higher frequency).
 9.IR SPECTRUM OF AMIDES

1° 2° 3°

• C=O stretching: approximately at 1680-1630 cm-1.

• N-H stretching (~ 3300 cm-1):

i) primary amides (-NH2) gives 2 spikes near 3350 and 3180
cm-1.
ii) Secondary amides have 1 spike (-NH) at about 3300 cm-1.

• N-H bending: around 1640-1550 cm-1 for primary and secondary

amides.
IR SPECTRUM OF BUTANAMIDE (PRIMARY AMIDE)

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 IR SPECTRUM OF
N-METHYL-1-PIPERIDINECARBOXAMIDE
(SECONDARY AMIDE)

N-H stretch:
(~ 3300 cm-1) C=O stretch
 IR SPECTRUM OF
N,N-BIS(2-PHENOXYETHYL)PROPIONAMIDE (TERTIARY
AMIDE)

** No N-H stretching

C=O stretch
10. IR SPECTRUM OF ACID CHLORIDES

C=O stretching: appear in range

1810-1775 cm-1 in unconjugated
chlorides. Conjugation lowers the
frequency to 1780-1760 cm-1

C-Cl stretching: range

730-550 cm-1
IR SPECTRUM OF 3,3-DIMETHYLBUTYRYL
CHLORIDE

C=O stretch
C-Cl stretch
 11. IR SPECTRUM OF ANHYDRIDES

• C=O stretch:
- 2 bands, 1830-1800 cm-1 and 1775-1740 cm-1 with
variable relative intensity.
- Conjugation moves the absorption to a lower frequency.

• C-O stretch (multiple bands): range 1300-900 cm-1.

IR SPECTRUM OF ACETIC ANHYDRIDE

C=O stretch

C=O stretch
C-O stretch
NORMAL BASE VALUES FOR THE C=O STRETCHING
VIBRATIONS FOR CARBONYL GROUPS

Reference point

Compounds Frequencies (cm-1)

Amides 1670-1650
Aldehydes 1740-1720
Ketones 1725-1705
Carboxylic acids 1725-1700
Esters 1750-1730
Acid halides 1810-1780
Anhydrides 1830-1800 and 1775-1740
12. IR SPECTRUM OF A NITRILE

CN triple bond stretch: around

2250 cm-1, sharp, pointed shape
IR SPECTRUM OF BUTYRONITRILE

Graphics source: Wade, Jr., L.G. Organic Chemistry, 6th ed. Pearson Prentice Hall Inc., 2006
 Example 1
Predict two important IR absorption bands and their
corresponding wavenumbers associated with ethyl
butanoate

Types of Bond Wavenumber (cm-1)

C=O stretch (ester) 1750-1730

C-O stretch 1300-1000

 Example 2
Compare 1-butanol and 2-butanone based on the
characteristic wavenumbers of their IR spectra.

Answer

1-Butanol 2-Butanone
The presence of broad peak at The absence of broad peak at 3400-3200
3400-3200 cm-1 (OH) cm-1
The presence of intense peak at The absence of intense peak at
1300-1000 cm-1 (C-O) 1300-1000 cm-1
The absence of intense peak at The presence of intense peak at
1725-1705 cm-1 1725-1705 cm-1 (C=O ketone)
 Example 3
The following is the IR spectrum of an organic compound which has the molecular
formula C2H4O2.
1. Identify the homologues series of the compound.
2. Select two significant peaks associated with the compound from the given
spectrum. State the wavenumber and the bond associated with each peak
you selected.
 Answer:

O-H stretch C=O stretch

1. Carboxylic acid
2.
Wavenumber (cm-1) Types of Bond
3100 O-H stretching
1705 C=O stretching
 Example 4
Ethanol and dimethyl ether are constitutional isomers (C2H6O). Decide which compound
corresponds to the IR spectrum below. Explain your selection.
 Answer
The IR spectrum is belongs to ethanol.

Justification:

Wavenumber (cm-1) Types of Bond

3316 OH stretching
1090 C-O (alcohol) stretching
 Example 5

Predict which compound (propanal or propanone) corresponds to spectrum below.

Justify your answer.

2738

1730
 Answer
The IR spectrum is belonging to propanal.

Justification:

Wavenumber (cm-1) Types of Bond

2738 and 2820 C-H stretch (aldehyde)
1730 C=O stretch (aldehyde)
 Exercise 1

Oxidation of 1-butanol with PCC in CH2Cl2 yielded

an aldehyde identified as butanal. By using IR
analysis, how you would confirm the formation of
butanal.
 Exercise 2

Reacting an alcohol with molecular formula C4H10O

with Jones reagent gives compound X which would
also give a positive result with iodoform test and
negative result with Tollens test. Draw the structure
of X and using IR spectroscopy, state how you
would confirm that X has been synthesized.
 Exercise 3

Based on the IR analyses, indicate the distinguished

features in the spectra that differentiate the following pair
of compounds:

a. Ethanol and ethanal

b. Ethanoic acid and ethanol
 Exercise 4
Indicate which one of the following compounds corresponds to each of the IR spectra
shown below. State the wavenumber and the bond associated with each peak you selected
that allowed you to make the assignment.

G
 Exercise 5
Indicate which one of the following compounds corresponds to each of the IR spectra
shown below. State the wavenumber and the bond associated with each peak you selected
that allowed you to make the assignment.

G
 Exercise 6
Indicate which one of the following compounds corresponds to each of the IR spectra
shown below. State the wavenumber and the bond associated with each peak you selected
that allowed you to make the assignment.

G
 Exercise 7
Indicate which one of the following compounds corresponds to each of the IR spectra
shown below. State the wavenumber and the bond associated with each peak you selected
that allowed you to make the assignment.