IR Exercise

Match the following 10 compounds with the 10 spectra on the following pages. Label the major diagnostic
peaks on each spectrum to receive full credit.

5 4

6 8

2 9

10 1

3
7

Reference

Some IR Stretching Frequencies

3400-3250 cm-1 N–H (1˚, 2˚ amines) 1680-1640 cm-1 C=C (alkenes)

3500-3200 cm-1 O–H (alcohols) 1600-1585 cm-1 C–C (aromatics)

3100-3000 cm-1 C–H (alkenes, aromatics) 1500-1400 cm-1 C–C (aromatics)

3000-2850 cm-1 C–H (alkanes) 1335-1250 cm-1 C–N ( aromatic amines)

2830-2695 cm-1 C–H (aldehydes) 1250-1020 cm-1 C–N (aliphatic amines)

1750-1665 cm-1 C=O (see discussion on back) 1300-1050 cm-1 C–O (alcohols, esters)
Carbonyl Stretching Frequencies
The exact position of the carbonyl band in the 1760-1665 cm-1 range is determined by the constituents
neighboring the carbonyl group. Some examples are:

range type of carbonyl examples

1750-1735 cm-1 saturated aliphatic esters O

C R'
R O

1740-1720 cm-1 saturated aliphatic alde- O

hydes C
R H

1730-1715 cm-1 ,-unsaturated esters O

R' O C
C OR
"R OR

1715 cm-1 saturated aliphatic O

ketones C
R R'

1710-1665 cm-1 ,-unsaturated alde- O O

hydes and ketones R' O R' O C C
H R
C C
"R H "R R

Another way of looking at the correlation between wavenumber and functional group stretch:

H (or R) C C
O
N
increasing band intensity

H C
H
C
H
}

C
O
H H (or R)
O
C
H (or R) N
}

O
H

4400 4000 3750 3500 3250 3000 2750 2500 2250 2000 1750 1500 1250 1000 750 450 c
 1470

1 C-H Bend

2875

C-H Stretches
2910
STRESTRE
2955
T

2CH

2CH
3

3290
2CH
N-H

2
2CH
3 2797
C-H stretch
2850

2CH
2908

2CH
3
 2710

C-H stretches
2890

3
C-H stretch
2970
C=O stretch
1710

3055
Benzene C-H stretch

1450
1600
4 Benzene
bonds

1360

C=O 1690 1270

 1480

5 1085
3310 2870 C-O stretch
O-H stretch C-H stretches
2925
2950

6 3015
2880
1200
C-H stretches

1450
3310
O-H stretch
 2890

C-H stretches
7 2960

C=O stretch
1705

C-H stretch 2988

1380
1050
C=O stretch C-O stretches
1720 1230
9 =C-H 3085
1630
1475
C-H bend
998
C=C
C-H stretches
2875
901

2950
2908

3410

3350 1390
N-H stretches
(primary amines) C-N stretch
10
1600
N-H bend
(primary amines)
1500