Homework Help is Here – Start Your Trial Now!
Science
Chemistry
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..

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...
See similar textbooks
icon
Related questions
Question

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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 4 steps with 10 images

SEE SOLUTIONCheck out a sample Q&A here
Blurred answer
Knowledge Booster
Mass Spectrometry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY
SEE MORE TEXTBOOKS