spectroscopy infrared spectra. infrared spectra in this presentation are taken by permission from...
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![Page 1: Spectroscopy Infrared Spectra. Infrared spectra in this presentation are taken by permission from the SDBS web site: SDBSWeb:](https://reader034.vdocument.in/reader034/viewer/2022042615/56649d775503460f94a596ae/html5/thumbnails/1.jpg)
Spectroscopy
Infrared Spectra
![Page 2: Spectroscopy Infrared Spectra. Infrared spectra in this presentation are taken by permission from the SDBS web site: SDBSWeb:](https://reader034.vdocument.in/reader034/viewer/2022042615/56649d775503460f94a596ae/html5/thumbnails/2.jpg)
Infrared spectra in this presentation are taken by permission from the SDBS web site:
SDBSWeb: http://www.aist.go.jp/RIODB/SDBS/
![Page 3: Spectroscopy Infrared Spectra. Infrared spectra in this presentation are taken by permission from the SDBS web site: SDBSWeb:](https://reader034.vdocument.in/reader034/viewer/2022042615/56649d775503460f94a596ae/html5/thumbnails/3.jpg)
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Spectroscopy“seeing the unseeable”
Using electromagnetic radiation as a probe to obtain information about atoms and molecules that are too small to see.
Electromagnetic radiation is propagated at the speed of light through a vacuum as an oscillating wave.
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electromagnetic relationships:
λυ = c λ 1/υ
E = hυ E υ
E = hc/λ E 1/λ
λ = wave length
υ = frequency
c = speed of light
E = kinetic energy
h = Planck’s constant
λ
c
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Two oscillators will strongly interact when their energies are equal.
E1 = E2
λ1 = λ2
υ1 = υ2
If the energies are different, they will not strongly interact!
We can use electromagnetic radiation to probe atoms and molecules to find what energies they contain.
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some electromagnetic radiation ranges
Approx. freq. range Approx. wavelengths
Hz (cycle/sec) meters
Radio waves 104 - 1012 3x104 - 3x10-4
Infrared (heat) 1011 - 3.8x1014 3x10-3 - 8x10-7
Visible light 3.8x1014 - 7.5x1014 8x10-7 - 4x10-7
Ultraviolet 7.5x1014 - 3x1017 4x10-7 - 10-9
X rays 3x1017 - 3x1019 10-9 - 10-11
Gamma rays > 3x1019 < 10-11
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Infrared radiation
λ = 2.5 to 17 μm
υ = 4000 to 600 cm-1
These frequencies match the frequencies of covalent bond stretching and bending vibrations. Infrared spectroscopy can be used to find out about covalent bonds in molecules.
IR is used to tell:
1. what type of bonds are present
2. some structural information
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IR source sample prism detector
graph of % transmission vs. frequency
=> IR spectrum
4000 3000 2000 1500 1000 500
v (cm-1)
100
%T
0
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toluene
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Some characteristic infrared absorption frequencies BOND COMPOUND TYPE FREQUENCY RANGE, cm-1
C-H alkanes 2850-2960 and 1350-1470
alkenes 3020-3080 (m) and
RCH=CH2 910-920 and 990-1000
R2C=CH2 880-900
cis-RCH=CHR 675-730 (v)
trans-RCH=CHR 965-975
aromatic rings 3000-3100 (m) and
monosubst. 690-710 and 730-770
ortho-disubst. 735-770
meta-disubst. 690-710 and 750-810 (m)
para-disubst. 810-840 (m)
alkynes 3300 O-H alcohols or phenols 3200-3640 (b) C=C alkenes 1640-1680 (v)
aromatic rings 1500 and 1600 (v) C≡C alkynes 2100-2260 (v) C-O primary alcohols 1050 (b)
secondary alcohols 1100 (b)
tertiary alcohols 1150 (b)
phenols 1230 (b)
alkyl ethers 1060-1150
aryl ethers 1200-1275(b) and 1020-1075 (m) all abs. strong unless marked: m, moderate; v, variable; b, broad
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IR spectra of ALKANES
C—H bond “saturated”
(sp3) 2850-2960 cm-1
+ 1350-1470 cm-1
-CH2- + 1430-1470
-CH3 + “ and 1375
-CH(CH3)2 + “ and 1370, 1385
-C(CH3)3 + “ and 1370(s), 1395 (m)
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n-pentane
CH3CH2CH2CH2CH3
3000 cm-1
1470 &1375 cm-1
2850-2960 cm-1
sat’d C-H
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CH3CH2CH2CH2CH2CH3
n-hexane
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2-methylbutane (isopentane)
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2,3-dimethylbutane
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cyclohexane
no 1375 cm-1
no –CH3
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IR of ALKENES
=C—H bond, “unsaturated” vinyl
(sp2) 3020-3080 cm-1
+ 675-1000
RCH=CH2 + 910-920 & 990-1000
R2C=CH2 + 880-900
cis-RCH=CHR + 675-730 (v)
trans-RCH=CHR + 965-975
C=C bond 1640-1680 cm-1 (v)
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1-decene
910-920 & 990-1000 RCH=CH2
C=C 1640-1680
unsat’dC-H
3020-3080 cm-1
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4-methyl-1-pentene
910-920 & 990-1000 RCH=CH2
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2-methyl-1-butene
880-900
R2C=CH2
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2,3-dimethyl-1-butene
880-900
R2C=CH2
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IR spectra BENZENEs
=C—H bond, “unsaturated” “aryl”
(sp2) 3000-3100 cm-1
+ 690-840
mono-substituted + 690-710, 730-770
ortho-disubstituted + 735-770
meta-disubstituted + 690-710, 750-810(m)
para-disubstituted + 810-840(m)
C=C bond 1500, 1600 cm-1
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ethylbenzene
690-710, 730-770 mono-
1500 & 1600
Benzene ring
3000-3100 cm-1
Unsat’d C-H
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o-xylene
735-770
ortho
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p-xylene
810-840(m)
para
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m-xylene
meta
690-710, 750-810(m)
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styrene
no sat’d C-H
910-920 & 990-1000
RCH=CH2
mono
1640C=C
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2-phenylpropene
mono880-900
R2C=CH2
Sat’d C-H
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p-methylstyrene
para
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IR spectra ALCOHOLS & ETHERS
C—O bond 1050-1275 (b) cm-1
1o ROH 1050
2o ROH 1100
3o ROH 1150
ethers 1060-1150
O—H bond 3200-3640 (b)
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1-butanol
CH3CH2CH2CH2-OH
C-O 1o
3200-3640 (b) O-H
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2-butanol
C-O 2o
O-H
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tert-butyl alcohol
C-O 3oO-H
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methyl n-propyl ether
no O--H
C-O ether
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2-butanone
C=O
~1700 (s)
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C9H12
C-H unsat’d & sat’d
1500 & 1600benzene
monoC9H12 – C6H5 = -C3H7
isopropylbenzene
n-propylbenzene?
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n-propylbenzene
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isopropyl split 1370 + 1385
isopropylbenzene
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C8H6
C-H unsat’d
1500, 1600benzene
mono
C8H6 – C6H5 = C2H
phenylacetylene
3300
C-H
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C4H8
1640-1680
C=C
880-900
R2C=CH2
isobutylene CH3
CH3C=CH2
Unst’d
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Which compound is this?a) 2-pentanoneb) 1-pentanolc) 1-bromopentaned) 2-methylpentane
1-pentanol
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What is the compound?a) 1-bromopentaneb) 1-pentanolc) 2-pentanoned) 2-methylpentane
2-pentanone
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H2C CHCH2
CH3CH3
CH3CH2CH2CH2CH3
H2CH2C
CH2CH2CH2CH3
biphenyl allylbenzene 1,2-diphenylethane
o-xylene n-pentane n-butylbenzene
A
B
C
D
E
F
In a “matching” problem, do not try to fully analyze each spectrum. Look for differences in the possible compounds that will show up in an infrared spectrum.
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1
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2
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3
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4
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5
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6