-(C=O)CH=CHAr 0.67 0.14 0.21 -(C=O)OCH3 0.68 0.08 0.19 ---(C=O)OCH2CH3 0.69 0.06 0.17 -(C=O)OH 0.77 0.11 0.25 -(C=O)CI 0.76 0.16 0.33 —(C=O)NH, 0.46 0.09 0.17 -C=N 0.29 0.12 0.25 -F -0.32 -0.05 -0.25 -CI -0.02 -0.07 -0.13 -Br 0.13 -0.13 -0.08 -OH -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -0(C=0)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 -NH2 -0.71 -0.22 -0.62 -N(CH3)2 -0.68 -0.15 -0.73 -NH(C=O)R 0.14 -0.07 -0.27 NO₂ 0.87 0.20 0.35 ABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCl3ª cis H C=C trans gem Base value 5.28 ppm Group gem cis trans -R 0.45 -0.22 -0.28 -CH=CH2 1.26 0.08 -0.01 -CH₂OH 0.64 -0.01 -0.02 -CH2X (X=F, Cl, Br) 0.70 -0.11 -0.04 -(C=O)OH 0.97 1.41 0.71 -(C=O)OR 0.80 1.18 0.55 -(C=O)H 1.02 0.95 1.17 -(C=O)R 1.10 1.12 0.87 -(C=O)Ar 1.82 1.13 0.63 -Ar 1.38 0.36 -0.07 -Br 1.07 0.45 0.55 -CI 1.08 0.18 0.13 -OR 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -O(C=O)R 2.11 -0.35 -0.64 –NH,, NHR, –NR, 0.80 -1.26 1.21 -NH(C=O)R 2.08 -0.57 -0.72 € 4 2 5 TABLE 22.3 Additive parameters for predicting NMR chemical shifts of alkyl protons in CDCI₁₁ Base values Methyl 0.9 ppm Methylene 1.2 ppm Methine 1.5 ppm Group (Y) Alpha (a) substituent Beta (B) substituent Gamma (y) substituent H-C-Y H-C-C H- -R 0.0 0.0 0.0 -C=C 0.8 0.2 0.1 -C-C-Arb 0.9 0.1 0.0 -C=C(C=O)OR 1.0 0.3 0.1 -C=C-R 0.9 0.3 0.1 -C=C-Ar 1.2 0.4 0.2 -Ar 1.4 0.4 0.1 -(C=O)OH 1.1 0.3 0.1 -(C=O)OR 1.1 0.3 0.1 -(C=O)H 1.1 0.4 0.1 -(C=O)R 1.2 0.3 0.0 -(C=O)Ar 1.7 0.3 0.1 —(C=O)NH, 1.0 0.3 0.1 -(C=O)CI 1.8 0.4 0.1 -C=N 1.1 0.4 0.2 -Br 2.1 0.7 0.2 -Cl 2.2 0.5 0.2 -OH 2.3 0.3 0.1 -OR 2.1 0.3 0.1 -OAr 2.8 0.5 0.3 -O(C=O)R 2.8 0.5 0.1 -O(C=O)Ar 3.1 0.5 0.2 -NH₂ 1.5 0.2 0.1 -NH(C=O)R 2.1 0.3 0.1 —NH(C=O)Ar 2.3 0.4 0.1 ferences of 01 TABLE 22.4 hemical this tab Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppma Base value Group ortho meta para -CH3 -0.18 -0.11 -0.21 -CH(CH3)2 -0.14 -0.08 -0.20 -CH₂CI 0.02 -0.01 -0.04 -CH=CH₂ 0.04 -0.04 -0.12 -CH=CHAr 0.14 -0.02 -0.11 -CH=CHCO₂H 0.19 0.04 0.05 -CH=CH(C=O)Ar 0.28 0.06 0.05 (Continued) Group ortho meta para -Ar 0.23 0.07 -0.02 -(C=O)H 0.53 0.18 0.28 -(C=O)R 0.60 0.10 0.20 -(C=O)Ar 0.45 0.12 0.23 -(C=O)CH=CHAr 0.67 0.14 0.21 -(C=O)OCH3 0.68 0.08 0.19 ---(C=O)OCH2CH3 0.69 0.06 0.17 -(C=O)OH 0.77 0.11 0.25 -(C=O)CI 0.76 0.16 0.33 —(C=O)NH, 0.46 0.09 0.17 C=N 0.29 0.12 0.25 -F -0.32 -0.05 -0.25 -CI -0.02 -0.07 -0.13 -Br 0.13 -0.13 -0.08 -OH -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -0(C=0)R -0.27 0.02 -0.13 ―0(C=O)Ar -0.14 0.07 -0.09 ―NH₂ -0./T -0.22 -0.62
-(C=O)CH=CHAr 0.67 0.14 0.21 -(C=O)OCH3 0.68 0.08 0.19 ---(C=O)OCH2CH3 0.69 0.06 0.17 -(C=O)OH 0.77 0.11 0.25 -(C=O)CI 0.76 0.16 0.33 —(C=O)NH, 0.46 0.09 0.17 -C=N 0.29 0.12 0.25 -F -0.32 -0.05 -0.25 -CI -0.02 -0.07 -0.13 -Br 0.13 -0.13 -0.08 -OH -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -0(C=0)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 -NH2 -0.71 -0.22 -0.62 -N(CH3)2 -0.68 -0.15 -0.73 -NH(C=O)R 0.14 -0.07 -0.27 NO₂ 0.87 0.20 0.35 ABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCl3ª cis H C=C trans gem Base value 5.28 ppm Group gem cis trans -R 0.45 -0.22 -0.28 -CH=CH2 1.26 0.08 -0.01 -CH₂OH 0.64 -0.01 -0.02 -CH2X (X=F, Cl, Br) 0.70 -0.11 -0.04 -(C=O)OH 0.97 1.41 0.71 -(C=O)OR 0.80 1.18 0.55 -(C=O)H 1.02 0.95 1.17 -(C=O)R 1.10 1.12 0.87 -(C=O)Ar 1.82 1.13 0.63 -Ar 1.38 0.36 -0.07 -Br 1.07 0.45 0.55 -CI 1.08 0.18 0.13 -OR 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -O(C=O)R 2.11 -0.35 -0.64 –NH,, NHR, –NR, 0.80 -1.26 1.21 -NH(C=O)R 2.08 -0.57 -0.72 € 4 2 5 TABLE 22.3 Additive parameters for predicting NMR chemical shifts of alkyl protons in CDCI₁₁ Base values Methyl 0.9 ppm Methylene 1.2 ppm Methine 1.5 ppm Group (Y) Alpha (a) substituent Beta (B) substituent Gamma (y) substituent H-C-Y H-C-C H- -R 0.0 0.0 0.0 -C=C 0.8 0.2 0.1 -C-C-Arb 0.9 0.1 0.0 -C=C(C=O)OR 1.0 0.3 0.1 -C=C-R 0.9 0.3 0.1 -C=C-Ar 1.2 0.4 0.2 -Ar 1.4 0.4 0.1 -(C=O)OH 1.1 0.3 0.1 -(C=O)OR 1.1 0.3 0.1 -(C=O)H 1.1 0.4 0.1 -(C=O)R 1.2 0.3 0.0 -(C=O)Ar 1.7 0.3 0.1 —(C=O)NH, 1.0 0.3 0.1 -(C=O)CI 1.8 0.4 0.1 -C=N 1.1 0.4 0.2 -Br 2.1 0.7 0.2 -Cl 2.2 0.5 0.2 -OH 2.3 0.3 0.1 -OR 2.1 0.3 0.1 -OAr 2.8 0.5 0.3 -O(C=O)R 2.8 0.5 0.1 -O(C=O)Ar 3.1 0.5 0.2 -NH₂ 1.5 0.2 0.1 -NH(C=O)R 2.1 0.3 0.1 —NH(C=O)Ar 2.3 0.4 0.1 ferences of 01 TABLE 22.4 hemical this tab Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppma Base value Group ortho meta para -CH3 -0.18 -0.11 -0.21 -CH(CH3)2 -0.14 -0.08 -0.20 -CH₂CI 0.02 -0.01 -0.04 -CH=CH₂ 0.04 -0.04 -0.12 -CH=CHAr 0.14 -0.02 -0.11 -CH=CHCO₂H 0.19 0.04 0.05 -CH=CH(C=O)Ar 0.28 0.06 0.05 (Continued) Group ortho meta para -Ar 0.23 0.07 -0.02 -(C=O)H 0.53 0.18 0.28 -(C=O)R 0.60 0.10 0.20 -(C=O)Ar 0.45 0.12 0.23 -(C=O)CH=CHAr 0.67 0.14 0.21 -(C=O)OCH3 0.68 0.08 0.19 ---(C=O)OCH2CH3 0.69 0.06 0.17 -(C=O)OH 0.77 0.11 0.25 -(C=O)CI 0.76 0.16 0.33 —(C=O)NH, 0.46 0.09 0.17 C=N 0.29 0.12 0.25 -F -0.32 -0.05 -0.25 -CI -0.02 -0.07 -0.13 -Br 0.13 -0.13 -0.08 -OH -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -0(C=0)R -0.27 0.02 -0.13 ―0(C=O)Ar -0.14 0.07 -0.09 ―NH₂ -0./T -0.22 -0.62
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question
Answer 3,4 , and 6, if you can't answer DONT reject, I'll wait for a tutor that can answe4, you have to look at the tables than the chemicals with arrows labeled 3,4 and 6.
Transcribed Image Text:-(C=O)CH=CHAr
0.67
0.14
0.21
-(C=O)OCH3
0.68
0.08
0.19
---(C=O)OCH2CH3
0.69
0.06
0.17
-(C=O)OH
0.77
0.11
0.25
-(C=O)CI
0.76
0.16
0.33
—(C=O)NH,
0.46
0.09
0.17
-C=N
0.29
0.12
0.25
-F
-0.32
-0.05
-0.25
-CI
-0.02
-0.07
-0.13
-Br
0.13
-0.13
-0.08
-OH
-0.53
-0.14
-0.43
-OR
-0.45
-0.07
-0.41
-OAr
-0.36
-0.04
-0.28
-0(C=0)R
-0.27
0.02
-0.13
-O(C=O)Ar
-0.14
0.07
-0.09
-NH2
-0.71
-0.22
-0.62
-N(CH3)2
-0.68
-0.15
-0.73
-NH(C=O)R
0.14
-0.07
-0.27
NO₂
0.87
0.20
0.35
ABLE 22.5
Additive Parameters for Predicting NMR
Chemical Shifts of Vinyl Protons in CDCl3ª
cis
H
C=C
trans
gem
Base value
5.28 ppm
Group
gem
cis
trans
-R
0.45
-0.22
-0.28
-CH=CH2
1.26
0.08
-0.01
-CH₂OH
0.64
-0.01
-0.02
-CH2X (X=F, Cl, Br)
0.70
-0.11
-0.04
-(C=O)OH
0.97
1.41
0.71
-(C=O)OR
0.80
1.18
0.55
-(C=O)H
1.02
0.95
1.17
-(C=O)R
1.10
1.12
0.87
-(C=O)Ar
1.82
1.13
0.63
-Ar
1.38
0.36
-0.07
-Br
1.07
0.45
0.55
-CI
1.08
0.18
0.13
-OR
1.22
-1.07
-1.21
-OAr
1.21
-0.60
-1.00
-O(C=O)R
2.11
-0.35
-0.64
–NH,, NHR, –NR,
0.80
-1.26
1.21
-NH(C=O)R
2.08
-0.57
-0.72
€
4
2
5
Transcribed Image Text:TABLE 22.3
Additive parameters for predicting NMR chemical shifts of alkyl
protons in CDCI₁₁
Base values
Methyl
0.9 ppm
Methylene
1.2 ppm
Methine
1.5 ppm
Group (Y)
Alpha (a) substituent
Beta (B) substituent
Gamma (y) substituent
H-C-Y
H-C-C
H-
-R
0.0
0.0
0.0
-C=C
0.8
0.2
0.1
-C-C-Arb
0.9
0.1
0.0
-C=C(C=O)OR
1.0
0.3
0.1
-C=C-R
0.9
0.3
0.1
-C=C-Ar
1.2
0.4
0.2
-Ar
1.4
0.4
0.1
-(C=O)OH
1.1
0.3
0.1
-(C=O)OR
1.1
0.3
0.1
-(C=O)H
1.1
0.4
0.1
-(C=O)R
1.2
0.3
0.0
-(C=O)Ar
1.7
0.3
0.1
—(C=O)NH,
1.0
0.3
0.1
-(C=O)CI
1.8
0.4
0.1
-C=N
1.1
0.4
0.2
-Br
2.1
0.7
0.2
-Cl
2.2
0.5
0.2
-OH
2.3
0.3
0.1
-OR
2.1
0.3
0.1
-OAr
2.8
0.5
0.3
-O(C=O)R
2.8
0.5
0.1
-O(C=O)Ar
3.1
0.5
0.2
-NH₂
1.5
0.2
0.1
-NH(C=O)R
2.1
0.3
0.1
—NH(C=O)Ar
2.3
0.4
0.1
ferences of 01
TABLE 22.4
hemical
this tab
Additive parameters for predicting NMR
chemical shifts of aromatic protons in CDCI
7.36 ppma
Base value
Group
ortho
meta
para
-CH3
-0.18
-0.11
-0.21
-CH(CH3)2
-0.14
-0.08
-0.20
-CH₂CI
0.02
-0.01
-0.04
-CH=CH₂
0.04
-0.04
-0.12
-CH=CHAr
0.14
-0.02
-0.11
-CH=CHCO₂H
0.19
0.04
0.05
-CH=CH(C=O)Ar
0.28
0.06
0.05
(Continued)
Group
ortho
meta
para
-Ar
0.23
0.07
-0.02
-(C=O)H
0.53
0.18
0.28
-(C=O)R
0.60
0.10
0.20
-(C=O)Ar
0.45
0.12
0.23
-(C=O)CH=CHAr
0.67
0.14
0.21
-(C=O)OCH3
0.68
0.08
0.19
---(C=O)OCH2CH3
0.69
0.06
0.17
-(C=O)OH
0.77
0.11
0.25
-(C=O)CI
0.76
0.16
0.33
—(C=O)NH,
0.46
0.09
0.17
C=N
0.29
0.12
0.25
-F
-0.32
-0.05
-0.25
-CI
-0.02
-0.07
-0.13
-Br
0.13
-0.13
-0.08
-OH
-0.53
-0.14
-0.43
-OR
-0.45
-0.07
-0.41
-OAr
-0.36
-0.04
-0.28
-0(C=0)R
-0.27
0.02
-0.13
―0(C=O)Ar
-0.14
0.07
-0.09
―NH₂
-0./T
-0.22
-0.62
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