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 Tahle I shows a typical response in following the flow chart
or nuclear magnetic resonance spectrum by an experienced for this soectrum. The overall conclusion that a student will
chemist. A beginner, however, sees only a piece of paper with come to is that the following groups are present: OH, CHa and
a multitude of peaks. How is i t possible to "decode" the C-0 or C-C. We use infrared in coniunction with other
complicated spectrum? methods of identification. Students are kncouraged to make
We have devised flow charts which successfully assist the use of all available information at~nutthe compound when
beginner to become proficient. The use of a flow chart is not drawing conclusions.
totally revolutionary but merely attempts to incorporate in Table 2. Flow Chart Responses for NMR Spectrum of p-
a systematic method the approach which might he followed methoxybenzaldehyde
by an experienced chemist.'
The charts are designed primarily for the beginner. They Reference oeak at 6 = 0 identified
are comparatively simple in that more complex spectra will Molecular formulaC8H8O2
not he encountered by the user. The student can use the chart Number of hydrogens = 8
to help him or her ask the correct questions and look for var- NO peaks removed by D20
ious features in the spectrum, and then to draw some con- From integrated tram calculate number of hydragens at different chemical
shfits.
clusion. He or she soon learns a method of "attacking" the Note splitting pattern for each absorption.
interpretation. The chart will he discarded, or rather a new
chart will be built up in the student's own mind. Chemical shift Number of hydrogens Splining
Infrared 9.8 6 1 singlet
7.9 6 2 doublet
When studvinz infrared s ~ e d r aaccount
. must he taken not 7.0 6 2 doublet
only of the &ti& ofthe peaks hut also thpirsizes and shape. 3.8 6 3 singlet
The flow chart in Figure 1 enables this to he done. Examples
can he selected to develop the student's experience of inter- (luestian
preting these features. The spectrum of propan-2-01 is shown Region Box Answer Inference
in Figure 2. For this compound the sepdrum above 2700 cm-' -OH. AWH, NH absent
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 Consider 9.8 6 peak first.One
the flow chart (Fig. 1). No information can he obtained in hydrogen not in region 8.0-6.6 6
so unlikely to be attached to
answer toauestion 5, and this is a limitation to which students' aromatic ring. Possible CHO.
attention may be drawn. -OH w -COOH group (but
-OH and -COOH absent).
' Henson, R. C., and Stumbles, A. M., S d i w l Sci. Rev., 80,212,446 ArH. OH. COOH or CHO group
(1979).
present (but OH. -GOOH already
Table 1. Typical Student Response for Spectrum ol Llquld eliminated .: group must be
Contalnlng Carbon, Hydrogen, and Oxygen CHO).Subbacting CHO from
CsH~O~leavesC~H~O.
Ouestlon Need to go round the loop again.
Region Bax Answer Inference There are 2 doublets in the region
above 2700 cm-' 1 Yes 8.0-5.6 6 of 2 hyrogen each, so
2 yes -OH mesent these are likely to be different
hydmgansanachedloabenrene
ring, i.e.,a disubstituted ring.

4 yes aliphatic CH present

5 not known (broad ArH present.
absorption pdisubstitution with different
obscures this subsliiuents. Subtracting GsHl
region) fromC,H,O leaves CHIO.
2000-1500 cm-' 6 no C=O, aromatic. NH.
alkene groups absent 6.6-4.5 6
150o-ttoOcm-' 10 Yes Above 4.5 6 yes Isolated CH3 group. All peaks
11 Yes LO. C-N, or cc accounted for.This must be
present CH30-.
12 Yes CHs present
13 Ye5 CH2 or CHI present Conclusion: Groups found CHSO-, CHO
below 900 cm-' 14 Yes
15 no -CHI- absent.
aromatic,alkene or
mnOchiorO C-*I
possible
M compound is:
e;'
CHO

704 Journal of Chemical Education

 0START

YES NO

, NO

YES NO

NO

YES NO

C-C. C-0,C-N CH2 or CHI

Absence ofC-O
C-N,

* h k
4
CHa, C H ~ '

at region
t

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 some-
what 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 moi-
ecule. 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 con-

Figure 4 shows the NMR spectrum of p-methoxybenzal-

dehyde and Table 2 responses to the flow chart questions for
this compound.
Figure 2. Spe*rum ot propan-2-01.
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

(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 . * < ' > I . 8 1 I , . , , , .
problems. Figwe 4. NMR specrmm of C8Hfir (no peaks removed by D20).

VSTART Table of Sp1itti"g patterntern

Singlet Noadjacent leoupling) hydmgena

Qu&t l:3:3:1 3 adjacenlaguivalvalt hydwem

YES
OH. COOH. NH :

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

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

706 Journal of Chemical Education

 - 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 not coupled to CH formulaand proceed with

I
formula and proceed with
remainder.
t

formula and proceed with

remainder
t1
YES Refer to tableaf splitting

+
pattemn to deduce group present.

Volume 61 Number 8 August 1984 707