All of the shift for the protons attached to the atom are indicated expect one. Use the tables to predict the shift for the proton attached to the atom indicated by the arrow with the question mark. Report your answer in ppm to the tenths' place
All of the shift for the protons attached to the atom are indicated expect one. Use the tables to predict the shift for the proton attached to the atom indicated by the arrow with the question mark. Report your answer in ppm to the tenths' place
Introductory Chemistry: A Foundation
9th Edition
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Donald J. DeCoste
Chapter15: Solutions
Section: Chapter Questions
Problem 1CR
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All of the shift for the protons attached to the atom are indicated expect one. Use the tables to predict the shift for the proton attached to the atom indicated by the arrow with the question mark. Report your answer in ppm to the tenths' place
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Signatures
U
v ab x, x
-CH,
-CH(CH,),
-CH,CI
-CH-CH,
-CH=CHAr
-0.18
-0.11
-0.21
-0,14
0.02
-0.08
--0.20
-0.01
Typical proton-proton coupling constants
-0.04
TABLE 22.6
-0.12
-0.11
0.04
-0.04
0.14
-0.02
Arrangment of protons
J(Hz)
Arrangement
protons
J(Hz)
Arrangement of protons
J(Hz)
-CH=CHCO,H
-CH=CH(C=O)Ar
0.19
0.04
0.05
0.28
0.06
0.05
(Continued)
10 to 16
O to 3
Free rotation
H.
-H
8 to 13
11 to 14
12 to 18
H
r Magnetic Resonance Spectroscopy
371
Anti
H.
Group
ortho
meta
para
-Ar
0.23
0.07
-0.02
2 to 4
8 to 13
6 to 12
-(C=O)H
-(C-O)R
0.53
0.18
0.28
0.60
0.10
0.20
Gauche
H.
-(C=O)Ar
0.45
0.12
0.23
-(C-O)CH=CHA.
-(C=O)OCH,
-(C=0)OCH,CH,
(C=O)OH
-(C=0)CI
-(C=O)NH,
-CEN
-F
0.67
0.68
0.14
0.21
0.08
0.19
0.69
0.06
0.17
0.77
0.11
0.25
6 to 9
2 to 6
4 to 10
0.76
0.16
0.33
0.46
0.09
0.17
0.29
0.12
0.25
-0.32
-0.05
-0.25
-0.13
-0.08
-CI
-0.02
-0.07
-Br
0.13
-0.13
1 to 3
2 to 5
0.5 to 2
-0.43
-0.41
-OH
-0.53
-0.14
-OR
-0.45
-0.07
-OAr
-0.36
-0.04
-0.28
-O(C=O)R
-O(C=O)Ar
-0.27
0.02
-0.13
-0.14
-0.71
-0.68
0.07
-0.09
-NH,
-N(CH,),
-NH(C=O)R
-NO,
-0.22
-0.62
O to 1
-0.15
-0.73
H.
H.
0.14
-0.07
-0.27
0.87
0.20
0.35
a. Base value is the measured chemical shift of benzene in CDCI, (1% solution).
Additive Parameters for Predicting NMR
Chemical Shifts of Vinyl Protons in CDCI,a
TABLE 22. 5
cis
H
Additive parameters for predicting NMR chemical shifts of alkyl
protons in CDCI,
TABLE 22.3
Base values
trans
gem
Methyl
Methylene
Methine
0.9 ppm
1.2 ppm
1.5 ppm
Base value
5.28 ppm
Group (Y)
Alpha (a) substituent
Beta (B) substituent
Gamma (y) substituent
Group
gem
cis
trans
-R
0.45
-0.22
-0.28
H-
-Y
H-
-Y
H
-0.01
-CH=CH,
–CH,OH
-CH,X (X=F, CI, Br)
{C=O)OH
-(C=O)OR
1.26
0.08
-R
0.0
0.0
0.64
-0.02
-0.04
0.0
-0.01
-C=C
-C=C-Ar
-C=C(C=O)OR
-C=C-R
0.8
0.2
0.1
0.70
-0.11
0.9
0.1
0.0
0.71
0.55
1.0
0.3
0.1
0.97
1.41
0.9
0.3
0.1
0.80
1.18
-C=C-Ar
1.2
0.4
0.2
-(C=O)H
-(C=0)R
-Ar
1.4
0.4
0.1
1.02
0.95
1.17
-(C=O)OH
-(C=O)OR
-(C=O)H
-(C=O)R
-(C=O)An
-(C=O)NH,
-(C=O)CI
-CEN
1.1
0.3
0.3
0.1
1.10
1.12
1.13
0.87
1.1
0.1
-(C=0)Ar
-Ar
1.1
0.4
0.1
1.82
0.63
1.2
0.3
0.0
1.38
0.36
-0.07
1.7
0.3
0.1
0.45
0.18
-Br
1.07
0.55
1.0
0.3
0.1
-CI
-OR
1.8
0.4
0.1
1.08
0.13
1.1
0.4
0.2
1.22
-1.07
-1.21
-Br
-CI
2.1
0.7
0.2
2.2
0.5
0.2
-OAr
1.21
-0.60
-1.00
-OH
2.3
0.3
0.1
-O(C=O)R
–NH, -NHR, –NR,
-NH(C=O)R
2.11
-0.35
-0.64
-OR
2.1
0.3
0.1
0.80
-1.26
1.21
-OAr
-O(C=OR
-O(C=O)Ar
-NH,
-NH(C=O)R
2.8
0.5
0.3
2.8
0.5
0.1
2.08
-0.57
-0.72
3.1
0.5
0.2
1.5
0.2
0.1
a. There may be small differences in the chemical-shift values calculated from this
table and those measured from individual spectra.
2.1
0.3
0.1
-NH(C=O)Ar
2.3
0.4
0.1
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