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By using the attached correlation tables for H1 NMR, calculate the expected hydrogen shifts (each one)of propiophenone and coumarin(show each step of calculations). Write what table are you using and which hydrogen is it ..labeled as (A, B,C etc).  Then, Compare with the attached observed hydrogen shifts from the spectra..

By using the attached correlation tables for H1 NMR, calculate the expected hydrogen shifts (each one)of propiophenone and coumarin(show each step of calculations). Write what table are you using and which hydrogen is it ..labeled as (A, B,C etc).  Then, Compare with the attached observed hydrogen shifts from the spectra..

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.SE: Something Extra
Problem 40AP: From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their...
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By using the attached correlation tables for H1 NMR, calculate the expected hydrogen shifts (each one)of propiophenone and coumarin(show each step of calculations). Write what table are you using and which hydrogen is it ..labeled as (A, B,C etc). 
Then, Compare with the attached observed hydrogen shifts from the spectra.. 

The structure of the compound: a There is possibility of 5 signals in the NMR spectrum. Peaks Ha Hb Hc Hd He Ha Hb Hc Hd He propiophenone Hf Chemical Shift Peaks The structure of the compound is: e H 1.18 ppm triplet 3.0 ppm quartet 2H 7.97 ppm doublet 2H 7.53 ppm multiplet 2H 7.63 ppm triplet 1H Multiplicity Integration a H. 3H H b H There is 6 signals in the NMR spectrum. Chemical Multiplicity Integration Shift 6.42 ppm doublet 1H 7.8 ppm doublet 1H 7.5 ppm doublet 1H 7.28 ppm multiplet 1H 7.53 ppm multiplet 1H 7.32 ppm doublet 1H a coumarin
Transcribed Image Text:The structure of the compound: a There is possibility of 5 signals in the NMR spectrum. Peaks Ha Hb Hc Hd He Ha Hb Hc Hd He propiophenone Hf Chemical Shift Peaks The structure of the compound is: e H 1.18 ppm triplet 3.0 ppm quartet 2H 7.97 ppm doublet 2H 7.53 ppm multiplet 2H 7.63 ppm triplet 1H Multiplicity Integration a H. 3H H b H There is 6 signals in the NMR spectrum. Chemical Multiplicity Integration Shift 6.42 ppm doublet 1H 7.8 ppm doublet 1H 7.5 ppm doublet 1H 7.28 ppm multiplet 1H 7.53 ppm multiplet 1H 7.32 ppm doublet 1H a coumarin
752 OH -CH3 C Substituent Substituent -R (alky) 0.9 -NH₂ -C-C 1.6 -NHCH 2.8 -C=C 1.8 _NH CO-R 2.8 -C₂H₁ 2.3 N -NR₂ -NH₂ -CO-NR₂ 20 -NO₂ 100 -CO-OR 2.0 C=O -CO-OH 2.1 S -SH -CO-R 2.1 -SR COH 2.2 -OR -CO-C.H 2.6 -OH -C=N 2.2 -O-C₂Hs 2.2 -D-CO-CH. 2.7 3.1 4.3 OH Table 33.3 Chemical Shifts of Methyl Groups Attached to Different Substituents с X UNIT 33• NUCLEAR MAGNETIC RESONANCE 8 table R stands for any alkyl group C C=O X base -H (trans) -CH₂OH (cis) -CH5 (gem) total Jobs = 6.62 ppm CH, CH-COOCH3 CH₂CH=CH₂ OCH3 alkynes -1 -Br -C -F -CO-NR₂ -CO-OR attached to-C6Hs 8 table = 2.3 ppm (8 obs=2.35 ppm) ACH₂)-1.25 ppm + x +oy -H -R (alkyl) -CH₂-C₂H₂ -CH₂OR -C=C -C-C (conj.) -C=C -C.Hs R is any alkyl group. Substituent aldehydes -R (alky) -C-C -CHC -GH₂ -1 -Br -C -CO-OR -CO-OH -CO-NR₂ -CO-R-CO-H -CO-GH₂ base Table 33.4 Shielding Constants of Substituents Attached to Methylene and Methine Groups -C=N total X-CH₂-Y Substituent -OH C=O-CO-OR (conj.) -CO-OH -CO-OH (conj.) -CO-R -CO-H Example of the use of Table 33.3 base -CO-OR 5.28 ppm 0 -0.02 ppm 1.43 ppm 6.69 ppm total -CcHs -C=C Stable 0 1.50 ppm 0.7 ppm 21 ppm 4.3 ppm Jobs = 4.22 ppm 2 Stable pem 0.98 1.26 0.50 1.43 CH₂- 3.35 ppm Jobs = 3.39 ppm 1.37 0.84 0.68 1.00 0.69 1.10 1.03 H e 0.0 0.8 0.9 13 0.7 0.8 1.0 1.2 1.6 1.2 1.4 1.9 20 1.25 ppm 1.3 ppm 0.8 ppm Z -5.28 ppm+++ 0 0 0.44 -0.26 -0.29 1.05 -0.29 -0.32 0.67 -0.02 -0.07 -0.04 -0.21 0.08 -0.01 Table 33.5 Shielding Constants of Substituents Attached to Alkenes Example of the use of Table 33.4 Methylene 8 An example of how to use Table 33.5 is given below. attached to-CO-OR å table=2.0 ppm (8 obs=2.0 ppm) N 0.35 0.10 0.39 0.06 S O total =0 O -O-CO-R Methine X 'OCH3 X-CH-Y I Z (CH) 1.50 ppm + x + ax + o₂ 1.7-1.8 R-C=C-H Ar-C=C-H R-C=C-H R-C=C-C=C-H aliphatic: R-CO-H 28-32 2.7-3.1 1.8-2.0 9-10 aromatic: Ar-CO-H 9.6-10.5 Ar is any aryl group: R" has at least a double bond in conjugation. -OR -OH base N S "For systems where the alkene, the substituent, or both are conjugated. R stands for any alkyl group. 8 table base 1.50 ppm 3-C6H5 3x1.3 ppm 1 Substituent _NH::-NHR NR _NH CH. -NH-CO-R -NO₂ -SH:-SR H -O-CH -O-CO-R -D-COCH, 1.25 ppm -CO-OR 0.7 ppm Cl 2.0 ppm total 0.93 0.35 1.15 0.56 1.02 0.33 1.35 0.74 -OR 0.97 0.39 O -OC₂H₂ 1.13 0.81 0.97 1.21 8 table -C=N -1 -Br -a -F Substituent 2.5 5.4 ppm Jobs = 5.55 ppm 3.2 CH₂OH Table 33.7 Chemical Shift of Hydrogens on Unsaturated Carbons Compound 2.6 Example of the use of Table 33.5 4.3 -O-CO-R 2.0 3.95 ppm Jobs = 4.10 ppm 2.1 3.2 3.4 3.7 3.7 3.9 “NH:: -NHR NK: -NH-CH -NH-CO-R -NO₂ -SH:-SR 33.14 CHEMICAL Compound Formates: RO-CO-H Formamides: R₂N-CO-H Imines: R-N-CRH Alkenes: C-C-H Aromatics: Ar-H attached to-O-CO-R & table = 3.7 ppm (obs=3.6 ppm) pm 0.23 & 1.14 1.04 1.00 1.54 8 table 8-82 8-87 1.00 • 1.0 1.8 2.1 3.2 1.3 base -H (trans) -CH₂OH (gem) -C6H5 (cis) total 8obs = 6.37 ppm 6-8 Table 33.5 Table 33.6 1.9 2.1 2.7 2.7 2.9 CICH₂COOCH, 0.69 -1.19 -1.31 -0.73 -0.81 2.30 2.08 -0.57 -0.72 0.62 1.87 1.32 -0.24 -0.04 CH 0.78 0.58 0.81 0.88 0.55 0.40 0.03 0.19 -0.40 -1.02 -1.06 -1.28 1.18 1.14 -0.65-1.05 -0.40 -0.67 2.09 5.28 ppm 0 0.67 ppm 0.39 ppm 6.34 ppm
Transcribed Image Text:752 OH -CH3 C Substituent Substituent -R (alky) 0.9 -NH₂ -C-C 1.6 -NHCH 2.8 -C=C 1.8 _NH CO-R 2.8 -C₂H₁ 2.3 N -NR₂ -NH₂ -CO-NR₂ 20 -NO₂ 100 -CO-OR 2.0 C=O -CO-OH 2.1 S -SH -CO-R 2.1 -SR COH 2.2 -OR -CO-C.H 2.6 -OH -C=N 2.2 -O-C₂Hs 2.2 -D-CO-CH. 2.7 3.1 4.3 OH Table 33.3 Chemical Shifts of Methyl Groups Attached to Different Substituents с X UNIT 33• NUCLEAR MAGNETIC RESONANCE 8 table R stands for any alkyl group C C=O X base -H (trans) -CH₂OH (cis) -CH5 (gem) total Jobs = 6.62 ppm CH, CH-COOCH3 CH₂CH=CH₂ OCH3 alkynes -1 -Br -C -F -CO-NR₂ -CO-OR attached to-C6Hs 8 table = 2.3 ppm (8 obs=2.35 ppm) ACH₂)-1.25 ppm + x +oy -H -R (alkyl) -CH₂-C₂H₂ -CH₂OR -C=C -C-C (conj.) -C=C -C.Hs R is any alkyl group. Substituent aldehydes -R (alky) -C-C -CHC -GH₂ -1 -Br -C -CO-OR -CO-OH -CO-NR₂ -CO-R-CO-H -CO-GH₂ base Table 33.4 Shielding Constants of Substituents Attached to Methylene and Methine Groups -C=N total X-CH₂-Y Substituent -OH C=O-CO-OR (conj.) -CO-OH -CO-OH (conj.) -CO-R -CO-H Example of the use of Table 33.3 base -CO-OR 5.28 ppm 0 -0.02 ppm 1.43 ppm 6.69 ppm total -CcHs -C=C Stable 0 1.50 ppm 0.7 ppm 21 ppm 4.3 ppm Jobs = 4.22 ppm 2 Stable pem 0.98 1.26 0.50 1.43 CH₂- 3.35 ppm Jobs = 3.39 ppm 1.37 0.84 0.68 1.00 0.69 1.10 1.03 H e 0.0 0.8 0.9 13 0.7 0.8 1.0 1.2 1.6 1.2 1.4 1.9 20 1.25 ppm 1.3 ppm 0.8 ppm Z -5.28 ppm+++ 0 0 0.44 -0.26 -0.29 1.05 -0.29 -0.32 0.67 -0.02 -0.07 -0.04 -0.21 0.08 -0.01 Table 33.5 Shielding Constants of Substituents Attached to Alkenes Example of the use of Table 33.4 Methylene 8 An example of how to use Table 33.5 is given below. attached to-CO-OR å table=2.0 ppm (8 obs=2.0 ppm) N 0.35 0.10 0.39 0.06 S O total =0 O -O-CO-R Methine X 'OCH3 X-CH-Y I Z (CH) 1.50 ppm + x + ax + o₂ 1.7-1.8 R-C=C-H Ar-C=C-H R-C=C-H R-C=C-C=C-H aliphatic: R-CO-H 28-32 2.7-3.1 1.8-2.0 9-10 aromatic: Ar-CO-H 9.6-10.5 Ar is any aryl group: R" has at least a double bond in conjugation. -OR -OH base N S "For systems where the alkene, the substituent, or both are conjugated. R stands for any alkyl group. 8 table base 1.50 ppm 3-C6H5 3x1.3 ppm 1 Substituent _NH::-NHR NR _NH CH. -NH-CO-R -NO₂ -SH:-SR H -O-CH -O-CO-R -D-COCH, 1.25 ppm -CO-OR 0.7 ppm Cl 2.0 ppm total 0.93 0.35 1.15 0.56 1.02 0.33 1.35 0.74 -OR 0.97 0.39 O -OC₂H₂ 1.13 0.81 0.97 1.21 8 table -C=N -1 -Br -a -F Substituent 2.5 5.4 ppm Jobs = 5.55 ppm 3.2 CH₂OH Table 33.7 Chemical Shift of Hydrogens on Unsaturated Carbons Compound 2.6 Example of the use of Table 33.5 4.3 -O-CO-R 2.0 3.95 ppm Jobs = 4.10 ppm 2.1 3.2 3.4 3.7 3.7 3.9 “NH:: -NHR NK: -NH-CH -NH-CO-R -NO₂ -SH:-SR 33.14 CHEMICAL Compound Formates: RO-CO-H Formamides: R₂N-CO-H Imines: R-N-CRH Alkenes: C-C-H Aromatics: Ar-H attached to-O-CO-R & table = 3.7 ppm (obs=3.6 ppm) pm 0.23 & 1.14 1.04 1.00 1.54 8 table 8-82 8-87 1.00 • 1.0 1.8 2.1 3.2 1.3 base -H (trans) -CH₂OH (gem) -C6H5 (cis) total 8obs = 6.37 ppm 6-8 Table 33.5 Table 33.6 1.9 2.1 2.7 2.7 2.9 CICH₂COOCH, 0.69 -1.19 -1.31 -0.73 -0.81 2.30 2.08 -0.57 -0.72 0.62 1.87 1.32 -0.24 -0.04 CH 0.78 0.58 0.81 0.88 0.55 0.40 0.03 0.19 -0.40 -1.02 -1.06 -1.28 1.18 1.14 -0.65-1.05 -0.40 -0.67 2.09 5.28 ppm 0 0.67 ppm 0.39 ppm 6.34 ppm
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