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.
O
C
1-butanol HOCH2CH2CH2CH3 acetophenone CH3

O
benzyl alcohol CH2OH ethyl acetate C CH2CH3
H 3C O

N-methylcyclo- NHCH3 1-hexene CH2=CHCH2CH2CH2CH3

hexylamine

aniline NH2 pentane CH3CH2CH2CH2CH3

O O
2-pentanone H3C C CH2CH2CH3 butyraldehyde H3CH2CH2C C
H

Reference

Some IR Stretching Frequencies

3400-3250 cm-1 NH (1, 2 amines) 1680-1640 cm-1 C=C (alkenes)

3500-3200 cm-1 OH (alcohols) 1600-1585 cm-1 CC (aromatics)

3100-3000 cm-1 CH (alkenes, aromatics) 1500-1400 cm-1 CC (aromatics)

3000-2850 cm-1 CH (alkanes) 1335-1250 cm-1 CN ( aromatic amines)

2830-2695 cm-1 CH (aldehydes) 1250-1020 cm-1 CN (aliphatic amines)

1750-1665 cm-1 C=O (see discussion on back) 1300-1050 cm-1 CO (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
C C
increasing band intensity

H
H
C
H
C
}

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

4400 4000 3750 3500 3250 3000 2750 2500 2250 2000 1750 1500 1250 1000 750 450 cm
1

3
 4

A
 7

A
10