Interpreting Infrared and Nuclear Magnetic Resonance

Spectra of Simple Organic Compounds for the Beginner

A. M. lngham and R. C. Henson
University of London Goldsmiths' College, New Cross, London SE14 6NW. England

A great deal of information may he gleaned from an infrared

or nuclear magnetic resonance spectrum by an experienced
chemist. A beginner, however, sees only a piece of paper with
a multitude of peaks. How is i t possible to "decode" the
complicated spectrum?
We have devised flow charts which successfully assist the
beginner to become proficient. The use of a flow chart is not
totally revolutionary but merely attempts to incorporate in
a systematic method the approach which might he followed
by an experienced chemist.'
The charts are designed primarily for the beginner. They
are comparatively simple in that more complex spectra will
not he encountered by the user. The student can use the chart
to help him or her ask the correct questions and look for various features in the spectrum, and then to draw some conclusion. He or she soon learns a method of "attacking" the
interpretation. The chart will he discarded, or rather a new
chart will be built up in the student's own mind.
Infrared
When studvinz infrared s ~ e d r aaccount
.
must he taken not
only of the &ti& ofthe peaks hut also thpirsizes and shape.
The flow chart in Figure 1 enables this to he done. Examples
can he selected to develop the student's experience of interpreting these features. The spectrum of propan-2-01 is shown
in Figure 2. For this compound the sepdrum above 2700 cm-'
shows a broad intense peak (due to -OH stretch) and a sharp
peak (due to aliphatic -CH s t r ~ t c h ) .
Students have no difficulty in answering questions 2-4 of
the flow chart (Fig. 1). No information can he obtained in
answer toauestion 5, and this is a limitation to which students'
attention may be drawn.

Tahle I shows a typical response in following the flow chart

for this soectrum. The overall conclusion that a student will
come to is that the following groups are present: OH, CHa and
C-0 or C-C. We use infrared in coniunction with other
methods of identification. Students are kncouraged to make
use of all available information at~nutthe compound when
drawing conclusions.
Table 2. Flow Chart Responses for NMR Spectrum of pmethoxybenzaldehyde
Reference oeak at 6 = 0 identified
Molecular formulaC8H8O2
Number of hydrogens = 8
NO peaks removed by D20
From integrated tram calculate number of hydragens at different chemical
shfits.
Note splitting pattern for each absorption.
Chemical shift
9.8 6
7.9 6
7.0 6
3.8 6

Number of hydrogens
2
2
3

(luestian
Region

Box

Answer

-OH
-OH

Answer
Yes

yes

Inference
-OH

and -COOH absent).

eliminated .: group must be

CHO).Subbacting CHO from
CsH~O~leavesC~H~O.
Need to go round the loop again.
There are 2 doublets in the region
8.0-5.6 6 of 2 hyrogen each, so
these are likely to be different

Ouestlon
1

w -COOH group (but

ArH. OH. COOH or CHO group

present (but OH. -GOOH already

Table 1. Typical Student Response for Spectrum ol Llquld

Contalnlng Carbon, Hydrogen, and Oxygen
Bax

AWH, NH absent

Consider 9.8 6 peak first.One

hydrogen not in region 8.0-6.6 6
so unlikely to be attached to
aromatic ring. Possible CHO.

(1979).

above 2700 cm-'

Inference
-OH.

' Henson, R. C., and Stumbles, A. M., S d i w l Sci. Rev., 80,212,446

Region

Splining
singlet
doublet
doublet
singlet

mesent

hydmgansanachedloabenrene

ring, i.e.,a disubstituted ring.

4

yes

not known (broad

2000-1500 cm-'

absorption
obscures this
region)
no

150o-ttoOcm-'

10

11
12
below 900 cm-'

704

13
14
15

Yes
Yes
Yes
Ye5
Yes
no

aliphatic CH present

C=O, aromatic. NH.

alkene groups absent

C-N, or cc
present
CHs present
CH2 or CHI present

present.
pdisubstitution with different
subsliiuents. Subtracting GsHl
fromC,H,O leaves CHIO.

ArH

6.6-4.5 6
Above 4.5 6

yes Isolated CH3 group. All peaks

accounted for.This must be
CH30-.

LO.

absent.
aromatic,alkene or
mnOchiorO C-*I
possible

Conclusion: Groups found CHSO-,

-CHI-

Journal of Chemical Education

M compound is:

e;'
CHO

CHO

0
START

YES

NO

NO

YES

NO

YES

NO

NO

C-C.

C-0,C-N

CH2 or CHI

Absence ofC-O

C-N,

CHa, C H ~ '

4
* h k

at region

Summarize findings

.Ald~hydes: CH sUeVh in the CHO group near 2720an-I

may hedoublet

Flgwe 1. Flow chart tor IR interpretation.

Volume 61

Number 8

August 1984

705

Figure 3 shows the proton NMR flow chart. This is somewhat longer and more comprehensive than the IR chart, hut
the approach is the same. The NMR spectrum is examined
region by region starting a t low field (high 6 number). From
the integrated intensities and splitting patterns within each
reeion the student learns to recoenize the vatterns which mav
heattributed t o definite groupings of atoms within the moiecule. The exact values of chemical shifts are not used at this
stage but can be used later in confirming the structure.
The flow chart does not require a detailed knowledge of
chemical shift, hut students are encouraged t o refer totables
of chemical shifts to confirm or to modify their overall conFigure 4 shows the NMR spectrum of p-methoxybenzaldehyde and Table 2 responses to the flow chart questions for
this compound.
Uslng the Flow Charts
Both the IR and NMR charts have been used as part of our
teaching for four years. Compared to the groups who had not
used flow charts, those who use them are

Figure 2. Spe*rum ot propan-2-01.

(1) impressively quicker,

(2) more competent,
(3) more confident,
(4) and progress more quickly and more confidently with these

topics than with others of comparable difficulty where flow

charts have not been used

Flow charts offer the advantages of enjoyment while using

them and the opportunity to work a t one's own pace. The
teacher is free to spend more time dealing with individual
problems.

<

'

>

Table of Sp1itti"g patterntern

START

Noadjacent leoupling) hydmgena

Singlet

Qu&t

YES

-OH, 4 O O H . -NH a k n t

Figure 3. Flow chart for NMR Interpretation. (continued on following page).

706

Figwe 4. NMR specrmm of C8Hfir (no peaks removed by D20).

Journal of Chemical Education

OH. COOH. NH

l:3:3:1

3 adjacenlaguivalvalt hydwem

Consid.. one absorption st a

time bur particularly for
peaks in the reginn near 7 6
theporsibility thstaromstii
proton. attached to the lame
ring may appear sf different
6 must he considered.

Cheek for eonsisteney

with molecular formula
and information.

Lmk at splitting & integration in region 4.5~0.06

I

C&group

YES

not coupled

to CH

formulaand proceed with

formula and proceed with

remainder.

formula and proceed with

remainder

t1

Refer to tableaf splitting

pattemn to deduce group present.

Volume 61

Number 8

August 1984

707