Characteristic IR Absorption Frequencies of Organic Functional Groups Functional Group Alcohol O-H O-H C-O Alkane C-H -C-H

Alkene =C-H =C-H C=C Alkyl Halide C-F C-Cl C-Br C-I Alkyne C-H Amine N-H C-N N-H Aromatic C-H C=C Carbonyl C=O Ether C-O Nitrile CN Nitro N-O stretch 1515-1560 & 1345-1385 strong, two bands stretch 2210-2260 medium stretch 1000-1300 (1070-1150) strong stretch stretch stretch 3000-3100 1400-1600 medium medium-weak, multiple bands stretch stretch bending 3300-3500 1080-1360 1600 medium (primary amines have two bands; secondary have one band, often very weak) medium-weak medium stretch stretch 3300 2100-2260 strong,sharp variable, not present in symmetrical alkynes stretch stretch stretch stretch 1000-1400 600-800 500-600 500 strong strong strong strong stretch bending stretch 3010-3100 675-1000 1620-1680 medium strong variable stretch bending 2850-3000 1350-1480 strong variable (stretch, Hbonded) (stretch, free) (stretch) 3200-3600 3500-3700 1050-1150 strong, broad strong, sharp strong Type of Vibration Characteristic Absorptions (cm-1) Intensity

Analysis of C-H out-of-plane bending can often distinguish substitution patterns Detailed Information on Carbonyl IR 1670-1820 strong (conjugation moves absorptions to lower wave numbers)

IR Absorption Frequencies of Functional Groups Containing a Carbonyl (C=O) Functional Group Type of Vibration Characteristic Absorptions (cm-1) Carbonyl C=O Acid C=O O-H C-O Aldehyde C=O =C-H Amide C=O N-H N-H Anhydride C=O Ester C=O C-O Ketone acyclic stretch 1705-1725 3-membered - 1850 4-membered - 1780 5-membered - 1745 6-membered - 1715 7-membered - 1705 1665-1685 1680-1700 strong stretch stretch 1735-1750 1000-1300 strong two bands or more stretch 1800-1830 & 1740-1775 two bands stretch stretch bending 1640-1690 3100-3500 1550-1640 strong unsubstituted have two bands stretch stretch 1740-1720 2820-2850 & 2720-2750 strong medium, two peaks stretch stretch stretch 1700-1725 2500-3300 1210-1320 strong strong, very broad strong stretch 1670-1820 strong (conjugation moves absorptions to lower wave numbers) Intensity

cyclic

stretch

strong

a,b-unsaturated aryl ketone

stretch stretch

strong strong