Infrared spectrum: interpret all absorptions from the 4000-1400 cm-1 region of the spectrum. Indicate which absorptions come from the ester and which from impurities. Submit the spectrum with your report.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Infrared spectrum: interpret all absorptions from the 4000-1400 cm-1 region of the spectrum. Indicate which absorptions come from the ester and which from impurities. Submit the spectrum with your report.
Correlation Table for Infrared Spectroscopy
Frequency of Intensity/Shape
absorption
(cm-1)
3650-3590
3600-3200
3400-2400
3500-3300
3340-3270
3100-3000
2960-2850
Strong/sharp
2850-2810 and Medium/ sharp
2750-2700
2260-2220
2260-2100
Medium to strong/
sharp
Weak to medium/
sharp
Strong/sharp
Strong/sharp
Strong/sharp
Strong/sharp
1730-1680* Strong/sharp
1800 and 1750
1810-1760
1750-1730
1740-1680
1720-1680
1700-1630
Strong/sharp
Strong/broad
Strong/ very broad
Medium to strong/
sharp
Strong/sharp
1680-1620
Weak to medium
1600-1450
Strong/sharp
Strong/sharp
Bond/Class of
Compounds
O-H/ alcohols, phenols
O-H/ alcohols, phenols
O-H/ carboxylic acids
N-H/ 1° and 2° amines
and amides
C(sp)-H/ terminal
alkynes
C(sp²)-H/alkenes,
aromatic compounds
C(sp³)-H/ alkanes
C-H/ aldehydes
C=N/nitriles
C=C/ alkynes
C=0/anhydrides
C=0/ acid chlorides
C=0/esters
C=0/ aldehydes
C=0/ ketones
C=0/amides
Additional Comments
Weak to medium/
C=C/ alkenes
sharp
Variable intensity/ C=C aromatic
sharp
Free (not hydrogen bonded)
OH group
Hydrogen bonded OH group
Dimers of carboxylic acids
1° amines and amides give
two absorptions, 2⁰ - one
Usually two absorptions,
one-2820, another -2720
Might not be visible in internal
alkynes
Always two absorptions
Aliphatic: 1740-1720
Aromatic: 1720-1680
C=0/ carboxylic acids Dimer, 1720-1700 aliphatic,
1700-1680 aromatic
Aliphatic: 1730-1700
Aromatic: 1700-1680
1° and 2° amides 1700-1670,
3⁰-1670-1630
1640-1620 if a conjugated
double bond
* Angle strain in the carbonyl group, caused by the size of a small ring, increases the frequency of
the absorption position of the C=0 bond of cyclic ketones; in cyclohexanone the absorption shows
at 1715 cm-¹, in cyclopentanone at 1750 cm-¹, and in cyclobutanone at 1785 cm-¹.
Transcribed Image Text:Correlation Table for Infrared Spectroscopy Frequency of Intensity/Shape absorption (cm-1) 3650-3590 3600-3200 3400-2400 3500-3300 3340-3270 3100-3000 2960-2850 Strong/sharp 2850-2810 and Medium/ sharp 2750-2700 2260-2220 2260-2100 Medium to strong/ sharp Weak to medium/ sharp Strong/sharp Strong/sharp Strong/sharp Strong/sharp 1730-1680* Strong/sharp 1800 and 1750 1810-1760 1750-1730 1740-1680 1720-1680 1700-1630 Strong/sharp Strong/broad Strong/ very broad Medium to strong/ sharp Strong/sharp 1680-1620 Weak to medium 1600-1450 Strong/sharp Strong/sharp Bond/Class of Compounds O-H/ alcohols, phenols O-H/ alcohols, phenols O-H/ carboxylic acids N-H/ 1° and 2° amines and amides C(sp)-H/ terminal alkynes C(sp²)-H/alkenes, aromatic compounds C(sp³)-H/ alkanes C-H/ aldehydes C=N/nitriles C=C/ alkynes C=0/anhydrides C=0/ acid chlorides C=0/esters C=0/ aldehydes C=0/ ketones C=0/amides Additional Comments Weak to medium/ C=C/ alkenes sharp Variable intensity/ C=C aromatic sharp Free (not hydrogen bonded) OH group Hydrogen bonded OH group Dimers of carboxylic acids 1° amines and amides give two absorptions, 2⁰ - one Usually two absorptions, one-2820, another -2720 Might not be visible in internal alkynes Always two absorptions Aliphatic: 1740-1720 Aromatic: 1720-1680 C=0/ carboxylic acids Dimer, 1720-1700 aliphatic, 1700-1680 aromatic Aliphatic: 1730-1700 Aromatic: 1700-1680 1° and 2° amides 1700-1670, 3⁰-1670-1630 1640-1620 if a conjugated double bond * Angle strain in the carbonyl group, caused by the size of a small ring, increases the frequency of the absorption position of the C=0 bond of cyclic ketones; in cyclohexanone the absorption shows at 1715 cm-¹, in cyclopentanone at 1750 cm-¹, and in cyclobutanone at 1785 cm-¹.
100
90
80
70
60
50
40
3500
3000
Orange ester
2018.39
2500
2000
Wavenumber cm-1
1466.25
1500
1000
500
Transcribed Image Text:100 90 80 70 60 50 40 3500 3000 Orange ester 2018.39 2500 2000 Wavenumber cm-1 1466.25 1500 1000 500
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