Question 10.4: Distinguishing Isomeric Compounds by IR Spectroscopy Acetone...
Distinguishing Isomeric Compounds by IR Spectroscopy
Acetone (CH_{3}COCH_{3}) and prop-2-en-1-ol (H_{2}C=CHCH_{2}OH) are isomers. How could you distinguish them by IR spectroscopy?
Strategy
Identify the functional groups in each molecule, and refer to Table 10.1.
TABLE 10.1 | |||||
Characteristic IR Absorptions of Some Functional Groups | |||||
Functional group | Absorption (cm^{-1}) | Intensity | Functional group | Absorption (cm^{-1}) | Intensity |
Alkane | Amine | ||||
C-H | 2850–2960 | Medium | N-H | 3300–3500 | Medium |
Alkene | C-N | 1030–1230 | Medium | ||
=C-H | 3020–3100 | Medium | Carbonyl | ||
C=C | 1640–1680 | Medium | compound | ||
Alkyne | C=O | 1670–1780 | Strong | ||
\equiv C-H | 3300 | Strong | Carboxylic acid | ||
C\equiv C | 2100–2260 | Medium | O-H | 2500–3100 | Strong, broad |
Alkyl halide | Nitrile | ||||
C-Cl | 600–800 | Strong | C=N | 2210–2260 | Medium |
C-Br | 500–600 | Strong | Nitro | ||
Alcohol | NO_{2} | 1540 | Strong | ||
O-H | 3400–3650 | Strong, broad | |||
C-O | 1050–1150 | Strong | |||
Arene | |||||
C-H | 3030 | Weak | |||
Aromatic ring | 1660–2000 | Weak | |||
1450–1600 | Medium |
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