1 C6H15N KEY Degrees of unsaturation Possible functional groups consistent with molecular formula none amine Diagnostic signal s 3300 3400 cm 1 two N H stretches Functional group consistent with spectrum 1 amine hexylamine 2 C6H15N Degrees of unsaturation Possible functional groups consistent with molecular formula none amine Diagnostic signal s 3290 cm 1 one N H stretch Functional group consistent with spectrum 2 amine dipropylamine 3 C7H6O KEY Degrees of unsaturation Five most likely contains aromatic ring Possible functional groups consistent with molecular formula Ether alcohol aldehyde or ketone Diagnostic signal s 2740 2850 cm 1 carbonyl C H stretch Functional group consistent with spectrum aldehyde benzaldehyde 4 C7H14 Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s alkene 3080 cm 1 sp2 C H stretch 1640 cm 1 C C stretch Functional group consistent with spectrum alkene 1 heptene 5 C6H12O KEY Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s alcohol cyclic no C C signal 3330 cm 1 O H stretch Functional group consistent with spectrum alcohol cyclohexanol 6 C5H8 Degrees of unsaturation two Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum diene monocyclic alkene alkyne 3300 cm 1 terminal alkyne C H stretch 2120 cm 1 triple bond stretch alkyne 1 pentyne 7 C7H5N KEY Degrees of unsaturation six Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum benzene ring cyano group 3060 cm 1 aromatic C C H stretch 2230 cm 1 triple bond stretch nitrile aromatic benzonitrile 8 C5H10O2 Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum acid ester diol ether 3100 cm 1 O H stretch 1710 cm 1 C O stretch carboxylic acid pentanoic acid 9 C8H16O2 KEY Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s acid ester diol ether 1730 cm 1 C O stretch 1100 1190 cm 1 alkoxy C O stretch Functional group consistent with spectrum ester isopropyl 2 methylbutyrate 10 C8H8O2 Degrees of unsaturation five Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum benzene ring acid ester diol ether 3060 3030 cm 1 sp2 C H stretch 1725 cm 1 C O stretch 1280 cm 1 alkoxy C O stretch ester methyl benzoate 11 C2H3OCl KEY Degrees of unsaturation one Possible functional groups consistent with molecular formula acid chloride chlorovinyl alcohol unlikely Diagnostic signal s 1805 cm 1 C O stretch Functional group consistent with spectrum acid chloride acetyl chloride 12 C7H5OCl Degrees of unsaturation five Possible functional groups consistent with molecular formula Diagnostic signal s acid chloride benzene ring 3070 cm 1 aromatic C H stretch 1775 cm 1 C O stretch 1620 1590 cm 1 sp2 C C stretch Functional group consistent with spectrum acid chloride benzoyl chloride 13 C2H5NO KEY Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s amide vinyl amine 3350 3170 cm 1 two N H stretches 1680 cm 1 C O stretch Functional group consistent with spectrum primary amide acetamide 14 C8H15NO Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s amide vinyl amine 3290 cm 1 N H stretch secondary amide 1640 cm 1 C O stretch Functional group consistent with spectrum secondary amide N cyclohexyl acetamide 15 C4H6O3 KEY Degrees of unsaturation two Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum anhydride 1830 1760 cm 1 C O symmetric and asymmetric stretches 1125 cm 1 C O stretch anhydride acetic anhydride 16 C5H8O Degrees of unsaturation two Possible functional groups consistent with molecular formula Diagnostic signal s aldehyde ketone alcohol ether 1745 cm 1 C O stretch no O H or aldehyde sp2 C H signals Functional group consistent with spectrum ketone cyclopentanone 17 C7H12O KEY Degrees of unsaturation two Possible functional groups consistent with molecular formula Diagnostic signal s aldehyde ketone alcohol ether 3310 cm 1 sp2 C H stretch 1690 cm 1 C O stretch no O H or aldehyde sp2 C H signals Functional group consistent with spectrum conjugated enone 5 methyl 3 hexen 2 one 18 C3H6O Degrees of unsaturation one Possible functional groups consistent with molecular formula Diagnostic signal s aldehyde ketone alcohol ether 2815 2715 cm 1 sp2 C H stretch 1740 cm 1 C O stretch no O H signal Functional group consistent with spectrum aldehyde propionaldehyde 19 C5H12O KEY Degrees of unsaturation none Possible functional groups consistent with molecular formula Diagnostic signal s alcohol ether 3375 cm 1 O H stretch 1190cm 1 C O stretch Functional group consistent with spectrum alcohol 2 methyl 2 butanol 20 C7H6O2 Degrees of unsaturation five Possible functional groups consistent with molecular formula Diagnostic signal s Functional group consistent with spectrum benzene ring acid ester 3070 cm 1 O H stretch 1700 cm 1 C O stretch 1250 cm 1 C O stretch acid benzoic acid