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Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.

Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.58P
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Question

Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.

Table 33.9 CHA -2.3 CH3CH3 6.1 15.7 C X 13.1 13C Chemical Shifts for Selected Hydrocarbons 24.9 24.3 16.2 Code -1 -Br -CI -F 25.2 Substituent -CH₂ -C=C -C=C -CH₂ -CO-NH, 22 -CO-OR 21 C=O-CO-OH 21 Terminal a 9 20 5 23 13.8 22.0 Table 33.10 13C Shielding Constants for Groups Attached to Alkyl Chains 3 3 27.7 B 10 6 6 9 17 Internal a 6 17 16 20 24 3 -CO-O- 24 4 -CO-R -CO-H -C=N 30 1 31 0 4 3 -7 11 20 11 31 11 32 68 9 63 22.5 1 Y Terminal B 8 4 7 2231 34.4 3 30.4 31.8 4 12 25 10 10 6 31.5 Terminal or internal Y -2 -1 -4 -2 -1 -2 -2 -2 -2 -2 -3 -1 -3 -4 -2.9 Y S 11.5 B Internal Z N -NR₂ 22.4 Substituent -NH₂ -NHR -NH₂+ -NR₂+ -NO₂ -SH -SR B Y Terminal 29 37 42 26 31 63 11 20 26.9 -OH 48 -OR 58 51 0-0-CO-R -O-CO-Ar 53 11 25.7 10 8 6 Internal a 24 31 8 6 8 24 5 4 57 12 11 7 126.2 41 51 45 B 10 6 6 4 11 855 25.4 23.0 Terminal or internal IT? | Table 33.11 13C Shielding Constants for Substituents Attached to Phenyl Rings c=128.5 ppm + Zattach 8c2= 128.5 ppm + Zortho Substituent -H -CH3 -CH₂ CH3 -CF₂ -C=C -C=C -C.Hs -CO-NH2 -CO-OR C=0 -CO-OH -CO-C -CO-CH3 CO-H C -C=N Jattach 0 9.3 15.7 2.6 9.5 -6.2 13.0 5.5 2.1 2.4 4.6 9.1 8.7 -15.8 R stands for any alkyl groups. Fortho 0 2 0.7 -0.1 -3.0 -2.8 -3.3 -0.6 -0.1 -2.8 -2.0 3.7 -1.1 -0.4 0.2 -0.5 0.4 -0.3 0.5 -1.0 -0.4 -1.0 1.2 0 1.6 -0.1 0.8 2.6 0.2 0.1 1.2 0.6 с 3.6 meta 0 C=O CH3 0.7 H Opara 0 Substituent -H -CH₂ -CH₂ CH₂ -CH₂OR -C=C -C=C -C₂Hs -CO-OR -CO-OH -CO-R -CO-H R stands for any alkyl group. H 5.0 4.4 5.0 6.6 4.3 5.8 COCH, 4.3 214 0 10.6 15.5 173 & X Table 33.12 13C Shielding Constants for Substituents Attached to Vinyl Carbons 6.2 4.7 15.0 13.4 Compound R-CO-H Ar-CO-H R-CO-R Ar-CO-R; Ar-CO-Ar H-CO-OH R-CO-OH Ar-CO-OH H-CO-O- R-CO-O Ar-CO-O N S O a -9.8 -9.7 13.6 -8.5 13.6 12.0 12.5 -11.0 -7.0 -11.0 B 209 7.0 9.0 5.9 13.0 Substituent -I -Br -C -F 8c3-128.5 ppm + O2mels 8C4 = 128.5 ppm + dzpara 163 -NH₂ -NR₂ 8 200-204 185-197 206-212 196-206 166 178-185 168-178 171 182-189 171-181 -NH-CO-R -N=N-C₂H5 -NO₂ -SH -SR O -OH -OCH3 -O-C6H5 -O-CO-R 8A-123.3 ppm +0₂ &a=123.3 ppm +2 Example of the use of Table 33.12 A base -COOR (₂) -CH3 (0₂) total N S O 123.3 ppm 6.2 ppm -9.8 ppm 119.7 ppm Sobs-122.3 ppm Substituent -C=N -Br -a -F -NR₂ -NR₂+ -NO₂ -SR -OR -OCO-R 210 184 Jattach -32.3 -5.6 6.4 35.0 NH 18.7 22.4 11.1 24.0 19.8 2.2 10.0 Table 33.13 13C Chemical Shifts of Carbonyls and Other Unsaturated Carbons Compound 198 15.2 -38.1 -7.9 26 24.9 H-CO-OR R-CO-OR Ar-CO-OR H-CO-NR₂ R-CO-NR₂ Ar-CO-NR₂ R-CO-C Ar-CO-C R-C=C-R; Ar-C=C-R R-C=N; Ar-C=N B base — COOR (₂) -CH₂ (0₂) total 169 26.9 -12.8 31.4 -14.6 -9.4 -6.2 29.1 23.0 dortho 9.9 3.3 0.3 -0.26 ܕܗ -12.9 -15.6 -9.9 -5.8 -4.9 7.3 <-1.0 -5.7 -34.1 <-29.0 16.0 19.8 -10.6 -0.9 22.3 19.0 -16.0 29.0 18.0 -39.0 -27.0 NH 14.3 0.7 -1.8 123.3 ppm 7.0 ppm 10.6 ppm 140.9 ppm obs=144.1 ppm 8 161-163 170-179 159-167 162-166 168-180 168-171 169-180 163-171 65-89 117-125 Opara -0.4 -1.3 -2.0 -4.4 1.0 -9.5 0.9 -11.7 0.2 -5.6 0.3 0.9 meta 2.6 1.8 1.2 -13.6 0.4 0.2 1.4 1.0 0.3 1.3 2.2 6.1 3.1 -3.5 -7.3 -8.1 -5.2 -2.3
Transcribed Image Text:Table 33.9 CHA -2.3 CH3CH3 6.1 15.7 C X 13.1 13C Chemical Shifts for Selected Hydrocarbons 24.9 24.3 16.2 Code -1 -Br -CI -F 25.2 Substituent -CH₂ -C=C -C=C -CH₂ -CO-NH, 22 -CO-OR 21 C=O-CO-OH 21 Terminal a 9 20 5 23 13.8 22.0 Table 33.10 13C Shielding Constants for Groups Attached to Alkyl Chains 3 3 27.7 B 10 6 6 9 17 Internal a 6 17 16 20 24 3 -CO-O- 24 4 -CO-R -CO-H -C=N 30 1 31 0 4 3 -7 11 20 11 31 11 32 68 9 63 22.5 1 Y Terminal B 8 4 7 2231 34.4 3 30.4 31.8 4 12 25 10 10 6 31.5 Terminal or internal Y -2 -1 -4 -2 -1 -2 -2 -2 -2 -2 -3 -1 -3 -4 -2.9 Y S 11.5 B Internal Z N -NR₂ 22.4 Substituent -NH₂ -NHR -NH₂+ -NR₂+ -NO₂ -SH -SR B Y Terminal 29 37 42 26 31 63 11 20 26.9 -OH 48 -OR 58 51 0-0-CO-R -O-CO-Ar 53 11 25.7 10 8 6 Internal a 24 31 8 6 8 24 5 4 57 12 11 7 126.2 41 51 45 B 10 6 6 4 11 855 25.4 23.0 Terminal or internal IT? | Table 33.11 13C Shielding Constants for Substituents Attached to Phenyl Rings c=128.5 ppm + Zattach 8c2= 128.5 ppm + Zortho Substituent -H -CH3 -CH₂ CH3 -CF₂ -C=C -C=C -C.Hs -CO-NH2 -CO-OR C=0 -CO-OH -CO-C -CO-CH3 CO-H C -C=N Jattach 0 9.3 15.7 2.6 9.5 -6.2 13.0 5.5 2.1 2.4 4.6 9.1 8.7 -15.8 R stands for any alkyl groups. Fortho 0 2 0.7 -0.1 -3.0 -2.8 -3.3 -0.6 -0.1 -2.8 -2.0 3.7 -1.1 -0.4 0.2 -0.5 0.4 -0.3 0.5 -1.0 -0.4 -1.0 1.2 0 1.6 -0.1 0.8 2.6 0.2 0.1 1.2 0.6 с 3.6 meta 0 C=O CH3 0.7 H Opara 0 Substituent -H -CH₂ -CH₂ CH₂ -CH₂OR -C=C -C=C -C₂Hs -CO-OR -CO-OH -CO-R -CO-H R stands for any alkyl group. H 5.0 4.4 5.0 6.6 4.3 5.8 COCH, 4.3 214 0 10.6 15.5 173 & X Table 33.12 13C Shielding Constants for Substituents Attached to Vinyl Carbons 6.2 4.7 15.0 13.4 Compound R-CO-H Ar-CO-H R-CO-R Ar-CO-R; Ar-CO-Ar H-CO-OH R-CO-OH Ar-CO-OH H-CO-O- R-CO-O Ar-CO-O N S O a -9.8 -9.7 13.6 -8.5 13.6 12.0 12.5 -11.0 -7.0 -11.0 B 209 7.0 9.0 5.9 13.0 Substituent -I -Br -C -F 8c3-128.5 ppm + O2mels 8C4 = 128.5 ppm + dzpara 163 -NH₂ -NR₂ 8 200-204 185-197 206-212 196-206 166 178-185 168-178 171 182-189 171-181 -NH-CO-R -N=N-C₂H5 -NO₂ -SH -SR O -OH -OCH3 -O-C6H5 -O-CO-R 8A-123.3 ppm +0₂ &a=123.3 ppm +2 Example of the use of Table 33.12 A base -COOR (₂) -CH3 (0₂) total N S O 123.3 ppm 6.2 ppm -9.8 ppm 119.7 ppm Sobs-122.3 ppm Substituent -C=N -Br -a -F -NR₂ -NR₂+ -NO₂ -SR -OR -OCO-R 210 184 Jattach -32.3 -5.6 6.4 35.0 NH 18.7 22.4 11.1 24.0 19.8 2.2 10.0 Table 33.13 13C Chemical Shifts of Carbonyls and Other Unsaturated Carbons Compound 198 15.2 -38.1 -7.9 26 24.9 H-CO-OR R-CO-OR Ar-CO-OR H-CO-NR₂ R-CO-NR₂ Ar-CO-NR₂ R-CO-C Ar-CO-C R-C=C-R; Ar-C=C-R R-C=N; Ar-C=N B base — COOR (₂) -CH₂ (0₂) total 169 26.9 -12.8 31.4 -14.6 -9.4 -6.2 29.1 23.0 dortho 9.9 3.3 0.3 -0.26 ܕܗ -12.9 -15.6 -9.9 -5.8 -4.9 7.3 <-1.0 -5.7 -34.1 <-29.0 16.0 19.8 -10.6 -0.9 22.3 19.0 -16.0 29.0 18.0 -39.0 -27.0 NH 14.3 0.7 -1.8 123.3 ppm 7.0 ppm 10.6 ppm 140.9 ppm obs=144.1 ppm 8 161-163 170-179 159-167 162-166 168-180 168-171 169-180 163-171 65-89 117-125 Opara -0.4 -1.3 -2.0 -4.4 1.0 -9.5 0.9 -11.7 0.2 -5.6 0.3 0.9 meta 2.6 1.8 1.2 -13.6 0.4 0.2 1.4 1.0 0.3 1.3 2.2 6.1 3.1 -3.5 -7.3 -8.1 -5.2 -2.3
D c с Propiophenone B CH 3 A Coumarin B 스
Transcribed Image Text:D c с Propiophenone B CH 3 A Coumarin B 스
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