IB Chemistry on Infrared Spectroscopy and IR Spectra analysis
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Transcript of IB Chemistry on Infrared Spectroscopy and IR Spectra analysis
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http://lawrencekok.blogspot.com
Prepared by Lawrence Kok
Tutorial on Infrared Spectroscopy and IR Spectra for organic molecules.
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Electromagnetic Radiation and Spectroscopy
Radiowaves
Nuclear spin
Nuclear Magnetic Resonance Spectroscopy
• Organic structure determination
• MRI and body scanning
Infra Red
Molecular vibration
Infra Red Spectroscopy
UV or visible
Transition of outer most valence electrons
• Organic structure determination
• Functional gp determination• Measuring bond strength• Measuring degree
unsaturation in fat• Measuring level of alcohol in
breath
Electromagnetic Radiation
UV Spectroscopy
Atomic Absorption Spectroscopy
• Quantification of metal ions• Detection of metal in various
samples
Electromagnetic Radiation Interact with Matter (Atoms, Molecules) = Spectroscopy
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• Spectroscopy measures the interaction of the molecules with electromagnetic radiation• Particles (molecule, ion, atom) can interact/absorb a quantum of light
Picture from: http://www.lpi.usra.edu/education/fieldtrips/2005/activities/ir_spectrum/
Spectroscopy
Electromagnetic Radiation
Nuclear spin
High Energy Radiation
Gamma/X ray
Transition of inner electrons
UV or visible
Transition of outer most valence electrons
Infra Red
Molecular vibration
Microwave
Molecular rotation
Radiowaves
Low Energy Radiation
Infra Red Spectroscopy
Nuclear Magnetic Resonance Spectroscopy
Ultra Violet Spectroscopy
Atomic Absorption Spectroscopy
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Diatomic molecule of same element DON’T absorb IR• Symmetrical diatomic bond will not absorb IR• No change in dipole moment as molecule
vibrate• No absorption of IR
Dipole change
No change in dipole moment
Molecular Vibration
Vibrational motion -result in a change dipole moment – IR active
Polar molecule will absorb IR• H-CI, as bond stretches, distance
between atoms increases, results in change in dipole moment• Absorb IR
Condition for molecular vibration to absorb a photon /IR• Vibration causing oscillation in developing a change
in dipole bet opposite charged centres• Vibration of bond in HCI will cause the dipole in
bond to oscillate• Causes a change in dipole momentOscillation of bonds - lead to oscillation of dipole - lead to change in
dipole moment
Molecular Vibration
Change in dipole moment
IR frequency = Natural frequency for bond – Resonance will happen.• HCI bond has natural vibrational frequency • IR frequency match the vibrational frequency in HCI, then IR is
absorb and molecule excited to vibrational state
• IR absorb by bond will result in greater vibration in amplitude
Diatomic Molecules
Vs
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For a molecule to absorb IR • Vibration within the molecule must cause a net change in dipole moment of molecule• Frequency of radiation matches the vibrational natural frequency of the molecule, then radiation will be absorbed, causing a change in amplitude of molecular vibration.• A permanent dipole is not necessary, only a change in dipole moment• Not all bond absorb at IR wavelength. For IR absorption a bond must have an electric dipole (bond polarity) that changes as it vibrates.• Molecules absorb IR – cause changes in modes of vibration (stretching/bending)
http://catalog.flatworldknowledge.com/bookhub/4309?e=averill_1.0-ch02_s01http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter__4%3A_Structure_Determination_I/Section_4.2%3A__Infrared_spectroscopy
Infrared Spectroscopy and Molecular Vibration
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For a molecule to absorb IR • Vibration within the molecule must cause a net change in dipole moment of molecule• Frequency of radiation matches the vibrational natural frequency of the molecule, then radiation will be absorbed, causing a change in amplitude of molecular vibration.• A permanent dipole is not necessary, only a change in dipole moment• Not all bond absorb at IR wavelength. For IR absorption a bond must have an electric dipole (bond polarity) that changes as it vibrates.• Molecules absorb IR – cause changes in modes of vibration (stretching/bending)
http://catalog.flatworldknowledge.com/bookhub/4309?e=averill_1.0-ch02_s01http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter__4%3A_Structure_Determination_I/Section_4.2%3A__Infrared_spectroscopy
Infrared Spectroscopy and Molecular Vibration
Molecular Vibration
Stretching Mode Bending Mode
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For a molecule to absorb IR • Vibration within the molecule must cause a net change in dipole moment of molecule• Frequency of radiation matches the vibrational natural frequency of the molecule, then radiation will be absorbed, causing a change in amplitude of molecular vibration.• A permanent dipole is not necessary, only a change in dipole moment• Not all bond absorb at IR wavelength. For IR absorption a bond must have an electric dipole (bond polarity) that changes as it vibrates.• Molecules absorb IR – cause changes in modes of vibration (stretching/bending)
http://catalog.flatworldknowledge.com/bookhub/4309?e=averill_1.0-ch02_s01http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter__4%3A_Structure_Determination_I/Section_4.2%3A__Infrared_spectroscopy
Infrared Spectroscopy and Molecular Vibration
Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer • IR ACTIVE (change in dipole)• IR INACTIVE (No change in dipole)
Asymmetric Stretching• change in bond length• bond become shorter/longer• IR ACTIVE (change in dipole)• IR INACTIVE (No change in dipole)
Symmetric Bending• change in bond angle• bond angle bigger/smaller• IR ACTIVE (change in dipole)• IR INACTIVE (No change in dipole)
Asymmetric Bending• change in bond angle• bond angle bigger/smaller• IR ACTIVE (change in dipole)• IR INACTIVE (No change in dipole)
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Molecular Vibration
Stretching Mode Bending Mode
Molecular Vibration for Water and IR Spectrum.
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Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 3652• IR ACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 3756• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 1595• IR ACTIVE
Molecular Vibration for Water and IR Spectrum.
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http://backreaction.blogspot.kr/2009/01/water-is-blue-because-water-is-blue.htmlhttp://giantsoftheinfinitesimal.com/goi-education.htm
Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 3652• IR ACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 3756• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 1595• IR ACTIVE
Molecular Vibration for Water and IR Spectrum.
IR spectrum for water
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Molecular Vibration
Stretching Mode Bending Mode
Molecular Vibration for Sulfur Dioxide and IR Spectrum.
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Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 1150• IR ACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 1360• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 540• IR ACTIVE
Molecular Vibration for Sulfur Dioxide and IR Spectrum.
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http://backreaction.blogspot.kr/2009/01/water-is-blue-because-water-is-blue.htmlhttp://giantsoftheinfinitesimal.com/goi-education.htm
Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 1150• IR ACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 1360• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 540• IR ACTIVE
Molecular Vibration for Sulfur Dioxide and IR Spectrum.
IR spectrum for sulfur dioxide
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Molecular Vibration
Stretching Mode Bending Mode
Molecular Vibration for Carbon Dioxide and IR Spectrum.
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Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• Bond polarity cancel out• NO change in dipole moment• IR INACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 2349• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 667• IR ACTIVE
Molecular Vibration for Carbon Dioxide and IR Spectrum.
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http://backreaction.blogspot.kr/2009/01/water-is-blue-because-water-is-blue.htmlhttp://giantsoftheinfinitesimal.com/goi-education.htm
Molecular Vibration
Stretching Mode Bending Mode
Symmetric Stretching• change in bond length• bond become shorter/longer• Bond polarity cancel out• NO change in dipole moment• IR INACTIVE
Asymmetric Stretching• change in bond length• bond become shorter/longer• change in dipole moment• Absorb IR at 2349• IR ACTIVE
Symmetric Bending• change in bond angle• bond angle bigger/smaller• change in dipole moment• Absorb IR at 667• IR ACTIVE
Molecular Vibration for Carbon Dioxide and IR Spectrum.
IR spectrum for carbon dioxide
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Different bonds absorb IR radiation at frequency/wavenumber . Use IR to identify the bonds and the functional group in a molecule.Common functional groups• (COOH), (O-H), (C=O), (C=C), (C-O), (C-H)
IR spectra of organic compounds with different functional groups
IR Absorption by different types of bonds/functional gps
IR spectrum with different functional gps and fingerprint region
Fingerprinting region • Range from (1500-
400cm -1)• Specific to each
molecule
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IR spectra of organic compounds with different functional groups
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Propanal (CH3CH2CHO)• (2840-3000) → C-H stretch• (2720) → C-H stretch of CHO• (1680-1740) → C=O stretch
Hex-1-ene CH2=CH(CH2)3CH3
• (2840-3000) → C-H stretch• (1610-1680) → C-C stretch • (1200- 1400) → C-H bend
Hex-1-yne CH2≡CH(CH2)3CH3
• (3350) → C≡ C stretch• (2840-3000) → C-H stretch • (1200- 1400) → C-H bend
IR spectra of organic compounds with different functional groups
Chloromethane CH3CI• (2840-3000) → C-H stretch• (1200-1400) → C-H bend • (700-800) → C-CI stretch
Halogenoalkane Aldehyde
Alkene Alkyne
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IR spectra of organic compounds with different functional groups
Methanol (CH3OH)• (3230-3550) → O-H stretch Broad Absorption due to H bonding between molecules• (2840-3000) → C-H stretch• (1000-1300) → C-O stretch
Ethanol(CH3CH2OH)• (3230-3550) → O-H stretch Broad Absorption due to H bonding between molecules• (2840-3000) → C-H stretch• (1000-1300) → C-O stretch• (1200- 1400) → C-H bend
Phenol (C6H5OH)• (3230-3550) → O-H stretch Broad Absorption due to H bonding between molecules• (2840-3000) → C-H stretch• (1400-1500) → C=C aromatic stretch• (1000-1300) → C-O stretch
Benzoic acid (C6H5COOH)• (3230-3550) → O-H stretch Broad Absorption due to H bonding between molecules• (2840-3000) → C-H stretch• (1400-1500) → C=C aromatic stretch• (1000-1300) → C-O stretch• (1680-1740) → C=O stretch
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Spectra difference between Acid and Ester
Methanoic acid
Methanoic acid
Spectra difference between Acid and Alcohol
Ethyl Ethanoate
Methanol
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Spectra difference between Acid and Ester
Methanoic acid
Methanoic acid
Spectra difference between Acid and Alcohol
Ethyl Ethanoate
Methanol
Vs
Vs
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Spectra difference between Acid and Ester
Ethyl ethanoate (CH3COOCH2CH3)• (2840-3000) → C-H stretch• (1680-1740) → C=O stretch• (1000-1300) → C-O stretch
Methanoic acid (CH3COOH)• (3230-3550) → O-H stretch • (2840-3000) → C-H stretch• (1000-1300) → C-O stretch• (1680-1740) → C=O stretch
Methanoic acid (CH3COOH)• (3230-3550) → O-H stretch • (2840-3000) → C-H stretch• (1000-1300) → C-O stretch• (1680-1740) → C=O stretch
Methanoic acid
Methanoic acid
Spectra difference between Acid and Alcohol
Methanol (CH3OH)• (3230-3550) → O-H stretch • (2840-3000) → C-H stretch• (1000-1300) → C-O stretch
Ethyl Ethanoate
Methanol
Vs
Vs
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Propan -2-ol CH3CH(OH)CH3
Spectra difference between Alcohol and Ketone
Propanone CH3 CO-CH3
Hexan-1-0l CH3(CH2)4CH2OH Hexan-2-0ne CH3CO(CH2)3CH3
http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter__4%3A_Structure_Determination_I/Section_4.2%3A__Infrared_spectroscopy
IR spectra of organic compounds with different functional groups
Alcohol
Ketone
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Propan -2-ol CH3CH(OH)CH3
Spectra difference between Alcohol and Ketone
Propanone CH3 CO-CH3
Hexan-1-0l CH3(CH2)4CH2OH Hexan-2-0ne CH3CO(CH2)3CH3
http://chemwiki.ucdavis.edu/Organic_Chemistry/Organic_Chemistry_With_a_Biological_Emphasis/Chapter__4%3A_Structure_Determination_I/Section_4.2%3A__Infrared_spectroscopy
IR spectra of organic compounds with different functional groups
OH
↓
C - H
↓
C - H
↓
C - H
↓
C=O → ← C-H bend
C-H bend →
← C-H bend
C-H bend →
Alcohol
Ketone
Vs
Vs
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http://chemwiki.ucdavis.edu/Organic_Chemistry/Virtual_Textbook_of_OChem/Spectroscopy/Infrared_Spectroscopy
Match the functional groups with its correct Spectra
← C-H stretch
← C-H stretch
← C-H stretch
← C-H stretch
← C=O stretch C=O stretch →
O-H ↓
O-H ↓
← C-H bend
← C-H bend
C-H bend →
C-H bend →
C=C stretch →
Finger printing region
Finger printing region
Finger printing region
Finger printing region
2 methylpropanal (Aldehyde) Butan-2-one (Ketone) Cyclobutanol (Alcohol) 2 methylpropen-1-ol ( Alcohol + Alkene)
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http://chemwiki.ucdavis.edu/Organic_Chemistry/Virtual_Textbook_of_OChem/Spectroscopy/Infrared_Spectroscopy
Match the functional groups with its correct Spectra
2 methylpropanal (Aldehyde) Butan-2-one (Ketone)
2 methylpropen-1-ol ( Alcohol + Alkene)Cyclobutanol (Alcohol)
← C-H stretch
← C-H stretch
← C-H stretch
← C-H stretch
← C=O stretch C=O stretch →
O-H ↓
O-H ↓
← C-H bend
← C-H bend
C-H bend →
C-H bend →
C=C stretch →
Finger printing region
Finger printing region
Finger printing region
Finger printing region
2 methylpropanal (Aldehyde) Butan-2-one (Ketone) Cyclobutanol (Alcohol) 2 methylpropen-1-ol ( Alcohol + Alkene)
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Click here to animated Spectra Click here to search IR spectra
IR Spectra search for different Organic Molecules
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Acknowledgements
Thanks to source of pictures and video used in this presentation
Thanks to Creative Commons for excellent contribution on licenseshttp://creativecommons.org/licenses/
Prepared by Lawrence Kok
Check out more video tutorials from my site and hope you enjoy this tutorialhttp://lawrencekok.blogspot.com