-CH₂CI 9.3 0.3 0.2 0.0 -C6H5 13.1 -1.1 0.5 -1.1 -CH₂CH₂ 15.7 -0.6 -0.1 -2.8 -CH(CH3)2 20.2 -2.2 -0.3 -2.8 -C(CH3)3 22.4 -3.3 -0.4 -3.1 —NH(C=O)CH 9.7 -8.1 0.2 -4.4 -NH₂ 18.2 -13.4 0.8 -10.0 -NO₂ 19.9 -4.9 0.9 6.1 -0(C=O)CH₁ 22.4 -7.1 0.4 -3.2 -OH 26.9 -12.8 1.4 -7.4 -OC6H5 27.6 -11.2 -0.3 -6.9 -OCH, 31.4 -14.4 1.0 -7.7 TABLE 23.6 Additive parameters for predicting NMR chemical shifts of alkene carbon atoms in CDCI, Base value: CH2-CH₂ = 123.3 ppm Y-C=C-Y' Y-C-C=C-C-Y' Y-C-C-C-C-C-C-Y' a a' β B' Y Y' Group (Y) a β Y a' B' Y' -C-(sp³) 10.1 7.1 -1.5 -7.7 -2.5 1.0 -CH=CH₂ 14.5 2.9 -2.4 -5.8 -0.5 1.2 -C6H5 13.6 4.9 -2.5 -9.6 0.7 1.1 -OH 3.9 -6.1 -0.8 3.8 -0(C=O)CH3 17.9 -1.1 -6.7 -25.8 2.3 3.3 -OR 28.5 1.7 -4.9 -37.0 0.7 2.9 -Br -9.4 1.0 -5.1 -1.5 2.4 4.2 -CI 2.8 0.5 -6.1 2.7 --(C=O)OR 3.0 -2.7 -3.4 7.3 2.2 1.9 -(C=O)OH 4.7 -2.9 -4.3 9.9 3.2 3.2 -(C=O)H 14.7 -4.1 16.2 2.0 -(C=O)R 14.1 -2.9 -3.5 5.5 3.0 1.7 TABLE 23.7 Steric additivity parameters for predicting NMR chemical shifts of alkene carbon atoms in CDC Each pair of aa' cis substituents Each pair of aa geminal substituents Each pair of a'a' geminal substituents Each a methine substituent Each a quaternary substituent -1.1 ppm -4.8 ppm 2.5 ppm 2.3 ppm 4.6 ppm QUESTION 10 Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.@GMU 2020 QUESTION 11 Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 C-Y 9.1 TABLE 23.3 Group (Y) -C-(sp³) Additive parameters for predicting NMR chemical shifts of alkyl carbon atoms in CDCI, Base value: CH₁ = -2.3 ppm alpha (a) beta (ẞ) gamma (y) C-C-Y C-C-C-Y 9.4 -2.5 -CH=CH₂ 20.3 6.8 -2.6 -CH=CHR (cis) 13.4 6.9 -0.3 -CH-CHR (trans) 19.3 7.0 -0.3 -CH-CR₂ 14.4. 6.9 -0.3 -CH 22.5 8.9 -2.6 -C=C-H 5.7 7.4 -2.0 -C=C-R -NH₂ -NHR 4.7 7.7 -0.2 28.7 11.3 -5.2 40.9 5.2 -4.3 -NR₂ 36.7 7.6 -4.6 -OH 49.4 10.1 -6.3 —O(C=OCH, 50.9 5.9 -6.2 -OR 57.4 7.2 -5.9 -6.8 10.9 -1.6 -Br 20.1 10.2 -3.9 CI 30.0 10.0 -4.6 -F 70.5 7.8 -6.9 -(C=O)OR 20.5 2.3 -2.9 -(C=O)OH 20.5 2.0 -2.9 -(C=O)H 30.3 4.8 -2.9 -(C=O)R 30.0 1.3 -2.7 -(C=O)CH -4.9 -0.4 -2.7 TABLE 23.4 Steric additivity parameters in ppm for predicting NMR chemical shifts of alkyl carbon atoms in CDCI Type of a carbon atom Methylene Methine Quaternary 0.0 -1.1 -3.4 0.0 0.0 -2.5 -6.0 0.0 -3.7 -8.5 -10.0 -1.5 -8.0 -10.0 -12.5 Type of 13C nucleus Methyl Primary Secondary Tertiary Quaternary TABLE 23.5 Additive parameters for predicting NMR chemical shifts of aromatic carbons atoms in CDCl3 Base value: benzene = 128.5 ppm Group C-1 ortho meta para -34.1 8.9 1.6 -1.1 -Br -5.8 3.2 1.6 -1.6 6.3 0.4 1.4 -1.9 -F 34.8 -13.0 1.6 -1.1 -H 0.0 0.0 0.0 0.0 ---(C=O)OCH 3 2.0 1.2 -0.1 4.3 --(C=O)OH 2.1 1.6 -0.1 5.2 -(C=O)H 8.2 1.2 0.5 5.8 -(C=O)CH₁₂ 8.9 0.1 -0.1 4.4 -CH=CH2 8.9 -2.3 -0.1 -0.8 -CH3 9.2 0.7 -0.1 -3.0 -CH₂CI 9.3 0.3 0.2 0.0 -C6H5 0.5 -1.1
-CH₂CI 9.3 0.3 0.2 0.0 -C6H5 13.1 -1.1 0.5 -1.1 -CH₂CH₂ 15.7 -0.6 -0.1 -2.8 -CH(CH3)2 20.2 -2.2 -0.3 -2.8 -C(CH3)3 22.4 -3.3 -0.4 -3.1 —NH(C=O)CH 9.7 -8.1 0.2 -4.4 -NH₂ 18.2 -13.4 0.8 -10.0 -NO₂ 19.9 -4.9 0.9 6.1 -0(C=O)CH₁ 22.4 -7.1 0.4 -3.2 -OH 26.9 -12.8 1.4 -7.4 -OC6H5 27.6 -11.2 -0.3 -6.9 -OCH, 31.4 -14.4 1.0 -7.7 TABLE 23.6 Additive parameters for predicting NMR chemical shifts of alkene carbon atoms in CDCI, Base value: CH2-CH₂ = 123.3 ppm Y-C=C-Y' Y-C-C=C-C-Y' Y-C-C-C-C-C-C-Y' a a' β B' Y Y' Group (Y) a β Y a' B' Y' -C-(sp³) 10.1 7.1 -1.5 -7.7 -2.5 1.0 -CH=CH₂ 14.5 2.9 -2.4 -5.8 -0.5 1.2 -C6H5 13.6 4.9 -2.5 -9.6 0.7 1.1 -OH 3.9 -6.1 -0.8 3.8 -0(C=O)CH3 17.9 -1.1 -6.7 -25.8 2.3 3.3 -OR 28.5 1.7 -4.9 -37.0 0.7 2.9 -Br -9.4 1.0 -5.1 -1.5 2.4 4.2 -CI 2.8 0.5 -6.1 2.7 --(C=O)OR 3.0 -2.7 -3.4 7.3 2.2 1.9 -(C=O)OH 4.7 -2.9 -4.3 9.9 3.2 3.2 -(C=O)H 14.7 -4.1 16.2 2.0 -(C=O)R 14.1 -2.9 -3.5 5.5 3.0 1.7 TABLE 23.7 Steric additivity parameters for predicting NMR chemical shifts of alkene carbon atoms in CDC Each pair of aa' cis substituents Each pair of aa geminal substituents Each pair of a'a' geminal substituents Each a methine substituent Each a quaternary substituent -1.1 ppm -4.8 ppm 2.5 ppm 2.3 ppm 4.6 ppm QUESTION 10 Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.@GMU 2020 QUESTION 11 Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 C-Y 9.1 TABLE 23.3 Group (Y) -C-(sp³) Additive parameters for predicting NMR chemical shifts of alkyl carbon atoms in CDCI, Base value: CH₁ = -2.3 ppm alpha (a) beta (ẞ) gamma (y) C-C-Y C-C-C-Y 9.4 -2.5 -CH=CH₂ 20.3 6.8 -2.6 -CH=CHR (cis) 13.4 6.9 -0.3 -CH-CHR (trans) 19.3 7.0 -0.3 -CH-CR₂ 14.4. 6.9 -0.3 -CH 22.5 8.9 -2.6 -C=C-H 5.7 7.4 -2.0 -C=C-R -NH₂ -NHR 4.7 7.7 -0.2 28.7 11.3 -5.2 40.9 5.2 -4.3 -NR₂ 36.7 7.6 -4.6 -OH 49.4 10.1 -6.3 —O(C=OCH, 50.9 5.9 -6.2 -OR 57.4 7.2 -5.9 -6.8 10.9 -1.6 -Br 20.1 10.2 -3.9 CI 30.0 10.0 -4.6 -F 70.5 7.8 -6.9 -(C=O)OR 20.5 2.3 -2.9 -(C=O)OH 20.5 2.0 -2.9 -(C=O)H 30.3 4.8 -2.9 -(C=O)R 30.0 1.3 -2.7 -(C=O)CH -4.9 -0.4 -2.7 TABLE 23.4 Steric additivity parameters in ppm for predicting NMR chemical shifts of alkyl carbon atoms in CDCI Type of a carbon atom Methylene Methine Quaternary 0.0 -1.1 -3.4 0.0 0.0 -2.5 -6.0 0.0 -3.7 -8.5 -10.0 -1.5 -8.0 -10.0 -12.5 Type of 13C nucleus Methyl Primary Secondary Tertiary Quaternary TABLE 23.5 Additive parameters for predicting NMR chemical shifts of aromatic carbons atoms in CDCl3 Base value: benzene = 128.5 ppm Group C-1 ortho meta para -34.1 8.9 1.6 -1.1 -Br -5.8 3.2 1.6 -1.6 6.3 0.4 1.4 -1.9 -F 34.8 -13.0 1.6 -1.1 -H 0.0 0.0 0.0 0.0 ---(C=O)OCH 3 2.0 1.2 -0.1 4.3 --(C=O)OH 2.1 1.6 -0.1 5.2 -(C=O)H 8.2 1.2 0.5 5.8 -(C=O)CH₁₂ 8.9 0.1 -0.1 4.4 -CH=CH2 8.9 -2.3 -0.1 -0.8 -CH3 9.2 0.7 -0.1 -3.0 -CH₂CI 9.3 0.3 0.2 0.0 -C6H5 0.5 -1.1
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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Transcribed Image Text:-CH₂CI
9.3
0.3
0.2
0.0
-C6H5
13.1
-1.1
0.5
-1.1
-CH₂CH₂
15.7
-0.6
-0.1
-2.8
-CH(CH3)2
20.2
-2.2
-0.3
-2.8
-C(CH3)3
22.4
-3.3
-0.4
-3.1
—NH(C=O)CH
9.7
-8.1
0.2
-4.4
-NH₂
18.2
-13.4
0.8
-10.0
-NO₂
19.9
-4.9
0.9
6.1
-0(C=O)CH₁
22.4
-7.1
0.4
-3.2
-OH
26.9
-12.8
1.4
-7.4
-OC6H5
27.6
-11.2
-0.3
-6.9
-OCH,
31.4
-14.4
1.0
-7.7
TABLE 23.6
Additive parameters for predicting NMR chemical shifts of alkene
carbon atoms in CDCI,
Base value: CH2-CH₂ = 123.3 ppm
Y-C=C-Y'
Y-C-C=C-C-Y'
Y-C-C-C-C-C-C-Y'
a
a'
β
B'
Y
Y'
Group (Y)
a
β
Y
a'
B'
Y'
-C-(sp³)
10.1
7.1
-1.5
-7.7
-2.5
1.0
-CH=CH₂
14.5
2.9
-2.4
-5.8
-0.5
1.2
-C6H5
13.6
4.9
-2.5
-9.6
0.7
1.1
-OH
3.9
-6.1
-0.8
3.8
-0(C=O)CH3
17.9
-1.1
-6.7
-25.8
2.3
3.3
-OR
28.5
1.7
-4.9
-37.0
0.7
2.9
-Br
-9.4
1.0
-5.1
-1.5
2.4
4.2
-CI
2.8
0.5
-6.1
2.7
--(C=O)OR
3.0
-2.7
-3.4
7.3
2.2
1.9
-(C=O)OH
4.7
-2.9
-4.3
9.9
3.2
3.2
-(C=O)H
14.7
-4.1
16.2
2.0
-(C=O)R
14.1
-2.9
-3.5
5.5
3.0
1.7
TABLE 23.7
Steric additivity parameters for predicting NMR
chemical shifts of alkene carbon atoms in CDC
Each pair of aa' cis substituents
Each pair of aa geminal substituents
Each pair of a'a' geminal substituents
Each a methine substituent
Each a quaternary substituent
-1.1 ppm
-4.8 ppm
2.5 ppm
2.3 ppm
4.6 ppm
QUESTION 10
Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.@GMU 2020
QUESTION 11
Using tables 23.3-23.7, predict the shift for the carbon indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020
Transcribed Image Text:C-Y
9.1
TABLE 23.3
Group (Y)
-C-(sp³)
Additive parameters for predicting NMR
chemical shifts of alkyl carbon atoms in CDCI,
Base value: CH₁ = -2.3 ppm
alpha (a)
beta (ẞ)
gamma (y)
C-C-Y
C-C-C-Y
9.4
-2.5
-CH=CH₂
20.3
6.8
-2.6
-CH=CHR
(cis)
13.4
6.9
-0.3
-CH-CHR (trans)
19.3
7.0
-0.3
-CH-CR₂
14.4.
6.9
-0.3
-CH
22.5
8.9
-2.6
-C=C-H
5.7
7.4
-2.0
-C=C-R
-NH₂
-NHR
4.7
7.7
-0.2
28.7
11.3
-5.2
40.9
5.2
-4.3
-NR₂
36.7
7.6
-4.6
-OH
49.4
10.1
-6.3
—O(C=OCH,
50.9
5.9
-6.2
-OR
57.4
7.2
-5.9
-6.8
10.9
-1.6
-Br
20.1
10.2
-3.9
CI
30.0
10.0
-4.6
-F
70.5
7.8
-6.9
-(C=O)OR
20.5
2.3
-2.9
-(C=O)OH
20.5
2.0
-2.9
-(C=O)H
30.3
4.8
-2.9
-(C=O)R
30.0
1.3
-2.7
-(C=O)CH
-4.9
-0.4
-2.7
TABLE 23.4
Steric additivity parameters in ppm for
predicting NMR chemical shifts of alkyl carbon
atoms in CDCI
Type of a carbon atom
Methylene
Methine
Quaternary
0.0
-1.1
-3.4
0.0
0.0
-2.5
-6.0
0.0
-3.7
-8.5
-10.0
-1.5
-8.0
-10.0
-12.5
Type of 13C nucleus
Methyl
Primary
Secondary
Tertiary
Quaternary
TABLE 23.5
Additive parameters for predicting NMR
chemical shifts of aromatic carbons atoms in
CDCl3
Base value: benzene = 128.5 ppm
Group
C-1
ortho
meta
para
-34.1
8.9
1.6
-1.1
-Br
-5.8
3.2
1.6
-1.6
6.3
0.4
1.4
-1.9
-F
34.8
-13.0
1.6
-1.1
-H
0.0
0.0
0.0
0.0
---(C=O)OCH 3
2.0
1.2
-0.1
4.3
--(C=O)OH
2.1
1.6
-0.1
5.2
-(C=O)H
8.2
1.2
0.5
5.8
-(C=O)CH₁₂
8.9
0.1
-0.1
4.4
-CH=CH2
8.9
-2.3
-0.1
-0.8
-CH3
9.2
0.7
-0.1
-3.0
-CH₂CI
9.3
0.3
0.2
0.0
-C6H5
0.5
-1.1
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