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612
418
511
Inte-
gral
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm
1
H
1.30 1.25
307.51
314.64
319.53
321.78
326.65
333.79
Hz
4.35 4.30 4.25
1060.02
1067.15
1074.75
1081.97
1089.17
Hz
1
H NMR spectrum
recorded at 250.13 MHz
The Knoevenagel reaction between a malonic acid diester and an aldehyde yields a
product having the 250MHz
1
H NMR spectrum shown below.
Determine the structural formulae of the starting materials and the product. Assign as
many signals as possible. What is the solvent?
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5
ppm
1
H
1.30 1.25
307.51
314.64
319.53
321.78
326.65
333.79
Hz
4.35 4.30 4.25
1060.02
1067.15
1074.75
1081.97
1089.17
Hz
1 3 3 1
1
3 3
1
C
C
H
C
C
O O
O CH
2
CH
3
O
H
2
C
CH
3
might be reversed
might be reversed
protons of the
phenyl ring
Solution at a glance
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