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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

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
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

 

7.2 7.3 7.4 1. 8 1.7 ?
Transcribed Image Text:7.2 7.3 7.4 1. 8 1.7 ?
AutoSave OFF Document1 Home Insert Draw Design Layout References Mailings Review View Acrobat Tell me Share Comments Calibri (Bo... A A Аa v E v E - E v 12 >T A Styles Styles Pane Dictate Sensitivity Create and Share Adobe PDF Paste A v Request 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 Page 1 of 1 O words English (United States) Focus + 140% lili
Transcribed Image Text:AutoSave OFF Document1 Home Insert Draw Design Layout References Mailings Review View Acrobat Tell me Share Comments Calibri (Bo... A A Аa v E v E - E v 12 >T A Styles Styles Pane Dictate Sensitivity Create and Share Adobe PDF Paste A v Request 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 Page 1 of 1 O words English (United States) Focus + 140% lili
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