Use the HNMR spectra shown here to determine the structural formula for the unknown cited below. Begin by calculating the degree of unsaturation for the compound. This will help you determine the total number of pi bonds plus rings that are possible for the structure. The table of chemical shift values are provided.

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Use the HNMR spectra shown here to determine the structural formula for the unknown cited below. Begin by calculating the degree of unsaturation for the compound. This will help you determine the total number of pi bonds plus rings that are possible for the structure. The table of chemical shift values are provided.
Chemical Formula: C¸H100
Structure B
3H
2H
T
4
2
PPM
1
3.
Transcribed Image Text:Chemical Formula: C¸H100 Structure B 3H 2H T 4 2 PPM 1 3.
fneqpuency than the chemical shift of methylene protons (hydrogens attached to an sp
NH:
"The values are approximate because they are affected by neighboring substituents.
Approximate Values of Chemical Shifts for 'H NMR°
The Characteristic Values of C
Table 14.1
Approximate
chemical shift
Approximate
chemical shift
Type of proton
(ppm)
Type of proton
(ppm)
-CH3
0.85
-H-
2.5-4
-CH2-
1.20
Br-C-H
2.5-4
- CH-
1.55
Cl
H-
3-4
Le
-C=C-CH3
1.7
F-C-H
ne
rs
4-4.5
ne
-C-CH3
2.1
R-NH2
Variable, 1.5-4
R-OH
Variable, 2-5
CH3
2.3
opm
HO-
Variable, 4-7
-C=C-H
2.4
H-
6.5-8
R-0-CH3
3.3
H-
9.0-10
R-C=CH2
4.7
R
С-ОН
Variable, 10-12
R-C=C-H
5.3
Variable, 5-8
R R
spectrum
inds
n in Table
Carbon that
wironment. Similarly, the chemical
Lohift of methyl
Transcribed Image Text:fneqpuency than the chemical shift of methylene protons (hydrogens attached to an sp NH: "The values are approximate because they are affected by neighboring substituents. Approximate Values of Chemical Shifts for 'H NMR° The Characteristic Values of C Table 14.1 Approximate chemical shift Approximate chemical shift Type of proton (ppm) Type of proton (ppm) -CH3 0.85 -H- 2.5-4 -CH2- 1.20 Br-C-H 2.5-4 - CH- 1.55 Cl H- 3-4 Le -C=C-CH3 1.7 F-C-H ne rs 4-4.5 ne -C-CH3 2.1 R-NH2 Variable, 1.5-4 R-OH Variable, 2-5 CH3 2.3 opm HO- Variable, 4-7 -C=C-H 2.4 H- 6.5-8 R-0-CH3 3.3 H- 9.0-10 R-C=CH2 4.7 R С-ОН Variable, 10-12 R-C=C-H 5.3 Variable, 5-8 R R spectrum inds n in Table Carbon that wironment. Similarly, the chemical Lohift of methyl
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