IR Lesson 2: The IR Spectra and IR Peaks:

IR is presented in your Solomons text. Table 2.7 (page 79) in Solomons is a very helpful
reference tool. Figure 2.11 (page 80) in Solomons is the IR spectrum of octane. Note the
four peaks in the spectrum of octane that are correlated to particular bond vibrations. Of
those four correlations, only the ones for the C-H bond stretches near 2900 cm-1 would
you be expected to immediately recognize based upon your knowledge of characteristic
bonds. Please note that you are not expected to know which of the stretches is derived
from the methyl group (-CH3) and which is caused by the methylene groups (-CH2-).
Table III-2 (next page) contains the characteristic bond stretching information you must
memorize and learn to use in this course. Whenever you analyze an IR spectrum, you
will have to match the characteristic IR peaks to characteristic bonds and annotate the
spectrum similar to the way in which the spectrum in Figure 2.11 of Solomons is
annotated.

One thing that you will notice (and can use to your advantage when you try to correlate
the structure of a compound to its IR spectrum) is that bonds of different functional
groups give different types of signals. Of particular importance is the difference between
an OH stretch of a carboxylic acid and an alcohol/phenol or NH of an amine. The
carboxylic acid OH is VERY BROAD, covering the entire range listed like a wide
parabola. The alcohol/phenol OH is moderate in width, and the NH stretch, which occurs
in the same range, is relatively narrow in width. Peak shape is an important feature in IR,
especially for OH or NH stretch. You must memorize both cm-1 values and peak shape
for the bonds listed on the next page.
TYPE OF BOND FUNCTIONALITY PEAK SHAPE IN SPECTRA
Typical cm-1 Range for cm-1
O-H R-CO2H Very broad, strong peak,
2500 – 3600 2500 – 3600
O-H R-OH Broad, strong peak,
3300 3200 – 3600
N-H R-NH2 & R-CONH2 Narrow, medium peak for each N-H bond,
3300 3300 – 3500
Csp-H R-C≡C-H Narrow, strong peak
3300 3300
Csp2-H R2C=CHR & Average width, medium intensity peak,
3050 Aromatics 3000 – 3100
Csp3-H R3C-H Average width, medium to strong intensity,
2900 2850 – 2950
C≡C R-C≡C-H Sharp peak, weak intensity,
2150 2150
C≡Ν R-C≡N Sharp peak, medium intensity
2250 2250
C=C Alkenes Average width and variable intensity
1650 1650 – 1620
C=C Aromatics Average width and variable intensity
1600 1600, 1500, 1490 (could be any one, two or all three)
C=O Carbonyl Compounds Average width and very strong intensity,
1700 1630 - 1780, (usually near 1700)

Table III-2. Peak Correlation Values. MBM

The practice problems listed below refer to simulated IR spectra A-C, shown on the next
page.

Q20. Does IR A indicate the presence of an O-H

bond?

Q21. Is the O-H peak in spectrum A likely to be A20. Yes. The broad peak at about 3300 cm-1 is
part of an alcohol, phenol or a carboxylic acid? indicative of an O-H stretch.

Q22. What functional group(s) is (are) indicated A21. An alcohol is strongly indicated. The peak
IR spectrum B? at 1700 cm-1 indicates a carbonyl (part of a
carboxylic acid); however, the O-H peak is
moderately wide, not wickedly wide (as would
indicate a carboxylic acid) and so the safe bet
here is that the OH stretch is indicative of an
alcohol or phenol. Not a carboxylic acid. The
absence of any peaks at 1600 cm-1 (for C=C
aromatic) and 3050 cm-1 (for Csp2-H) further
indicates that the OH peak is from an alcohol and
not from a phenol. This is apparently a di-
functional compound, containing both an alcohol
and separate carbonyl functionality.

Q23. What functional group(s) is (are) indicated A22. An alkyne is indicated. The sharp peak at
IR spectrum C? 3300 cm-1 indicates a Csp-H stretch. But this
must be confirmed by finding the CC triple bond
stretch at 2150 cm-1. If you find a peak at 3300
cm-1 but not 2150 cm-1, you would lean towards
this being an amine.

A23. This IR indicates an alkene with additional

saturated carbons, such as 1-butene. The 3075
cm-1 peak indicates Csp2-H stretch (could be
aromatic or alkene). The peak at 2950 cm-1
indicates the saturated Csp3-H stretch. The peak
at 1650 cm-1 indicates that the compound is an
alkene and not an aromatic (1600 cm-1)
compound.
Simulated IR spectra for problems Q20 – Q23 on the previous page.

2900 1700
3300

IR Spectrum A

1500
2150 1380
3300

IR Spectrum B

3075 1650
2950

IR Spectrum C