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Number of hydrogens
2
2
3
(luestian
Region
Box
Answer
-OH
-OH
Answer
Yes
yes
Inference
-OH
Ouestlon
1
AWH, NH absent
(1979).
Inference
-OH.
Region
Splining
singlet
doublet
doublet
singlet
mesent
hydmgansanachedloabenrene
yes
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
present.
pdisubstitution with different
subsliiuents. Subtracting GsHl
fromC,H,O leaves CHIO.
ArH
6.6-4.5 6
Above 4.5 6
LO.
absent.
aromatic,alkene or
mnOchiorO C-*I
possible
-CHI-
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
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
<
'
>
START
Singlet
Qu&t
YES
-OH, 4 O O H . -NH a k n t
OH. COOH. NH
l:3:3:1
3 adjacenlaguivalvalt hydwem
C&group
YES
not coupled
to CH
t1
Volume 61
Number 8
August 1984
707