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Topic 10D - IR 2022

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26 views32 pages

Topic 10D - IR 2022

Uploaded by

David Lei
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© © All Rights Reserved
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Infrared (IR) spectroscopy

Molecular vibration
Covalent bonds absorb IR, and molecules vibrate
after IR absorption
Different bonds require different radiation energy /
frequency to make them vibrate

IR spectra is used for determine structure of


organic molecules
Wavenumber
𝑐 = 𝑓𝜆 c = speed of light
1
𝑓=𝑐 𝑓 = frequency
𝜆
𝑓 = 𝑐 × wavenumber λ = wavelength
𝟏
𝑓 = 𝑐𝜈ҧ 𝐰𝐚𝐯𝐞𝐧𝐮𝐦𝐛𝐞𝐫 = ഥ
𝝂=𝝀

Wavenumber is the reciprocal of wavelength, with unit of cm-1


The larger the wavenumber, the higher the frequency

E = ℎ𝑓 ℎ = Planck’s constant
E = ℎ𝑐𝜈ҧ

The larger the wavenumber, the higher the energy of radiation is


IR spectrum is a plot of IR transmittance (reverse of absorbance)
against different wavenumbers of IR

We are interested in the peaks which shows significant absorption,


this tell us what functional groups are present
Fingerprint region: below 1500 cm-1
This region is unique for every compound – used as “fingerprint”
An exact match of the fingerprint region can help identify
unknown compound

C-C stretch, C-O stretch, C-H bend, C-X stretch in


halogenoalkanes appear in this region
Double bond region: 2000 cm-1 - 1500 cm-1
C=O stretch for aldehydes, ketones, carboxylic acids and esters
C=C stretch for alkenes

Triple bond region: 2500 cm-1 - 2000 cm-1


C C stretch for alkynes
C N stretch for nitriles
Single bond to H region: 4000 cm-1 - 2500 cm-1
C-H stretch for alkanes, alkenes and aldehyde

O-H stretch for alcohols, carboxylic acids


N-H stretch for amines
Wavenumber Bond Functional groups Intensity and shape
(cm-1) stretch
3750-3200 O-H alcohols medium to strong, broad
3500-3140 N-H amine, amide medium
3300-2500 O-H carboxylic acid medium to strong, broad
3095-3010 C-H alkene medium
2962-2853 C-H Alkane medium to strong
2900-2820 C-H Aldehyde weak
2775-2700
2260-2215 C N nitrile strong
2260-2100 C C alkyne medium to strong
1750-1680 C=O aldehyde, ketone, strong
carboxylic acid, ester
1669-1645 C=C alkene weak to medium
1300-1000 C-O alcohol, carboxylic acid, variable
ester
500-1400 C-X Halogenoalkane strong
Case study 1
• Identification of functional group isomers
Distinguish heptanal and heptan-4-one using their
IR spectra

Heptanal Heptan-4-one

Aldehyde Ketone

C=O stretch at 1750-1680 cm-1 C=O stretch at 1750-1680 cm-1


aldehyde C-H stretch
at 2920-2800 cm-1 and 2775-
2700 cm-1
Spectrum 1: heptanal C=O stretch at 1750-1680 cm-1

aldehyde C-H stretch at 2920-2800 cm-1 and 2775-2700 cm-1

C-H stretch
(aldehyde)
C-H stretch
(-CH3, -CH2-)

C=O stretch
C=O stretch at 1750-1680 cm-1
Spectrum 2: heptan-4-one
aldehyde C-H stretch is absent

C-H stretch
(-CH3, -CH2-) C=O stretch
Case study 2
• Monitoring the completeness of reaction

Propan-1-ol Propanal Propanoic acid

O-H stretch C=O stretch C=O stretch


at 3750-3500 cm-1 at 1750-1680 cm-1 at 1750-1680 cm-1

aldehyde C-H stretch O-H stretch


at 2920-2800 cm-1 at 3300-2500 cm-1
and 2775-2700 cm-1
Spectrum 3 : propanol
Alcohol has broad O-H stretch at 3750-3500 cm-1
(higher than carboxylic acid)

C-H stretch

C-O stretch
O-H stretch
Spectrum 4 : propanal
aldehyde C-H stretch at 2920-2800 cm-1 and 2775-2700 cm-1

C-H stretch
(aldehyde)

C-H stretch
(-CH3, -CH2-) C=O stretch
Spectrum 5: propanoic acid (C3H6O2)
Carboxylic acid has broader O-H stretch at 3300-2500 cm-1
(broader and lower than alcohol)
Carboxylic acid O-H stretch usually overlaps with C-H stretch

O-H stretch C-H stretch

C=O stretch
Spectrum 6: butane

C-H stretch
CH3CH2CH2CH3
Spectrum 7: Z-pent-2-ene
Alkene has C=C stretch at 1669-1645 cm-1

C=C stretch

C-H stretch
(-CH3, -CH2-)
C-H stretch
(=C-H)
Spectrum 8: hydroxypropanone (C3H6O2)
Broad O-H stretch at 3750-3300 cm-1 (higher than carboxylic acid)
C=O stretch at 1750-1680 cm-1 , no aldehyde C-H stretch

C-H stretch

O-H stretch
C=O stretch
O-H stretch
alcohol +
carboxylic acid

C-H stretch
C=O stretch
Spectrum 9: methyl ethanoate (C3H6O2)

C-H stretch

C-O stretch
(O-CH3)

C-O stretch
C=O stretch (O=C-O)
Spectrum 10: propylamine

Only primary amine shows


N-H symmetric (3300 cm -1) & asymmetric stretch (3400 cm -1)

N-H bend
N-H stretch-
symmetric &
asymmetric C-H stretch
Sample 11: propanenitrile
Nitrile has C N stretch at 2260-2215 cm-1

C stretch
C-H stretch
Past paper example 1 IAL 2017Oct U3 Q3
Compound W only contains carbon, hydrogen and oxygen. It has
only one function group.
The infrared spectrum of compound W:

(a) Using information from spectrum, name the functional group in W


Past paper example 1 IAL 2017Oct U3 Q3

(a) Using information from spectrum, name the functional group in W


The spectrum shows broad absorption around 3700-3200 cm-1 which
is resulted from O-H bond.
C=O absorption is absent around 1750-1680 cm-1.
W has a functional group of alcohol
Past paper example 1 IAL 2017Oct U3 Q3

Molecule of W has four carbon atoms. W does NOT react with


acidified potassium dichromate.
(b) Draw the structure of W

Explanation
W is a tertiary alcohol since it cannot be oxidised in acidified
dichromate. W has 4 carbon atoms.
W is 2-methylpropan-2-ol
Past paper example 2 IAL 2014May U2 Q21

Describe the features on the infrared spectrum of product


which could be used to determine whether an alcohol is
completely converted to an aldehyde.
Select some of the following infrared data to support your
answer.
Past paper example 2 IAL 2014May U2 Q21

• The spectrum of product aldehyde shows weak absorption at


2900-2820 cm-1 and 2775-2700 cm-1 which are resulted from
aldehyde C-H bond.
• Strong absorption for C=O bond in aldehyde at 1740-1720
cm-1 appears in spectrum
• The spectrum shows no O-H absorption at 3750 - 3200 and
3300-2500 cm-1
Conclusion
• Molecules vibrate when their bonds absorbs IR
radiation
• Different bonds absorb different frequencies of IR
Conclusion
• IR spectrum is a plot of IR transmittance against
wavenumber (reciprocal of wavelength)
• Uses of IR spectroscopy in organic chemistry
- Identify functional group isomers
- Monitor the completeness of reaction

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