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

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

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

ChapterL3: Carbon (13c) Nmr Spectroscopy

Section: Chapter Questions

Problem 8E

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