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11:40 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 H-C-C-Y 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 TABLE 22.4 Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppm³ 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)OCH 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 -ОН -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -O(C=O)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 ―NH₂ 0.71 การ -0.62 -N(CH.). -0.68 -0.15 -0.73 U.J 0.07 U.+1 -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 TABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, 22.5 Table cis H C=C trans gem Base value 5.28 ppm cis gem trans Group 0.45 -0.22 -R -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 <-Cl -OR 1.08 0.18 0.13 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -0(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 a. There may be small QUESTION 5 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 QUESTION 6 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020 QUESTION 7 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020

11:40 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 H-C-C-Y 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 TABLE 22.4 Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppm³ 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)OCH 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 -ОН -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -O(C=O)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 ―NH₂ 0.71 การ -0.62 -N(CH.). -0.68 -0.15 -0.73 U.J 0.07 U.+1 -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 TABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, 22.5 Table cis H C=C trans gem Base value 5.28 ppm cis gem trans Group 0.45 -0.22 -R -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 <-Cl -OR 1.08 0.18 0.13 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -0(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 a. There may be small QUESTION 5 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 QUESTION 6 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020 QUESTION 7 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020

Chemistry
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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11:40 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 H-C-C-Y 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 TABLE 22.4 Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppm³ 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)OCH 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 -ОН -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -O(C=O)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 ―NH₂ 0.71 การ -0.62 -N(CH.). -0.68 -0.15 -0.73
Transcribed Image Text:11:40 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 H-C-C-Y 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 TABLE 22.4 Additive parameters for predicting NMR chemical shifts of aromatic protons in CDCI 7.36 ppm³ 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)OCH 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 -ОН -0.53 -0.14 -0.43 -OR -0.45 -0.07 -0.41 -OAr -0.36 -0.04 -0.28 -O(C=O)R -0.27 0.02 -0.13 -O(C=O)Ar -0.14 0.07 -0.09 ―NH₂ 0.71 การ -0.62 -N(CH.). -0.68 -0.15 -0.73
U.J 0.07 U.+1 -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 TABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, 22.5 Table cis H C=C trans gem Base value 5.28 ppm cis gem trans Group 0.45 -0.22 -R -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 <-Cl -OR 1.08 0.18 0.13 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -0(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 a. There may be small QUESTION 5 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 QUESTION 6 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020 QUESTION 7 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020
Transcribed Image Text:U.J 0.07 U.+1 -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 TABLE 22.5 Additive Parameters for Predicting NMR Chemical Shifts of Vinyl Protons in CDCI, 22.5 Table cis H C=C trans gem Base value 5.28 ppm cis gem trans Group 0.45 -0.22 -R -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 <-Cl -OR 1.08 0.18 0.13 1.22 -1.07 -1.21 -OAr 1.21 -0.60 -1.00 -0(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 a. There may be small QUESTION 5 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer. GMU 2020 QUESTION 6 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020 QUESTION 7 Using tables 22.3, 22.4, and 22.5, predict the shift for the protons attached to the atom indicated by the arrow. Report your answer in ppm to the tenths' place. Don't include the units in the answer.OGMU 2020
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