could you help me work out these problem step by step

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
Section13.SE: Something Extra
Problem 33AP
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could you help me work out these problem step by step

Name:
Date:
Experiment 1: Green Diels Alder NMR
4. Consider the chemical equivalence (number of different kinds of protons) within the molecule.
Label each different type of proton with a lower-case letter. How many signals would be expected
to appear in the spectrum? Hint, the number of signals that should be in the spectrum may
overlapping in the true spectrum. Diastereotopic protons are not equivalent. (5 pts)
be
3
H3C-N
OH
5. What are diastereotopic protons? Which two protons in this molecule are diastereotopic? (5 pts)
6. Use the 'H NMR Chemical Shift Table to predict the ppm range expected for each chemically
equivalent proton listed in Problem 4. (7 pts)
Transcribed Image Text:Name: Date: Experiment 1: Green Diels Alder NMR 4. Consider the chemical equivalence (number of different kinds of protons) within the molecule. Label each different type of proton with a lower-case letter. How many signals would be expected to appear in the spectrum? Hint, the number of signals that should be in the spectrum may overlapping in the true spectrum. Diastereotopic protons are not equivalent. (5 pts) be 3 H3C-N OH 5. What are diastereotopic protons? Which two protons in this molecule are diastereotopic? (5 pts) 6. Use the 'H NMR Chemical Shift Table to predict the ppm range expected for each chemically equivalent proton listed in Problem 4. (7 pts)
8.5
Experiment 1: Green Diels Alder NMR
8.0
47
7.5
6.0
6.5
7.0
5.5
University of New Orleans
мил
and b
5.0
f1 (ppm)
H3C
N
4.5
Name:
4.0
T
4 OH
H
3.5
1
3.0
2.5
14
2.0
1.5
H₂O
1.0
0.5
Date:
0.0
80
70
-60
50
40
30
Directions: As you complete this post-lab, please watch the entire 'H-NMR video
posted in the manual. It will be very helpful!
20
1. Draw in all hydrogen atoms in the chemical structure. Remember that there are always four
bonds to carbon. (5 pts)
10
0
-10
2. How many hydrogen atoms are in the structure? (4 pts) 15
Hydrogen
3. The total number of hydrogen atoms in the chemical structure should equal the total number of
protons integrated in the spectrum. What is the total number of protons integrated in the spectrum?
Does the total number of hydrogen atoms in the structure match the total number of protons
integrated in the spectrum? Show your work. (5 pts)
11/2022
Transcribed Image Text:8.5 Experiment 1: Green Diels Alder NMR 8.0 47 7.5 6.0 6.5 7.0 5.5 University of New Orleans мил and b 5.0 f1 (ppm) H3C N 4.5 Name: 4.0 T 4 OH H 3.5 1 3.0 2.5 14 2.0 1.5 H₂O 1.0 0.5 Date: 0.0 80 70 -60 50 40 30 Directions: As you complete this post-lab, please watch the entire 'H-NMR video posted in the manual. It will be very helpful! 20 1. Draw in all hydrogen atoms in the chemical structure. Remember that there are always four bonds to carbon. (5 pts) 10 0 -10 2. How many hydrogen atoms are in the structure? (4 pts) 15 Hydrogen 3. The total number of hydrogen atoms in the chemical structure should equal the total number of protons integrated in the spectrum. What is the total number of protons integrated in the spectrum? Does the total number of hydrogen atoms in the structure match the total number of protons integrated in the spectrum? Show your work. (5 pts) 11/2022
Expert Solution
Step 1

Please find the following answers step by step as given in the problem.  

Part 1

 Chemistry homework question answer, step 1, image 1

1. From the structural distribution of the molecule we can think of H2, H3, H7 and H8 should come in one place-1 type

H1, H4, H6 and H9 ideally should appear together- 1 type

H10 and H11 being diastereotopic protons, they should appear in two different ppm values-2 types

H5 would come seperately - 1 type

OH proton H12 would appear differently- 1 type

H13 and H14 being chemically different would appear at two differetn ppm values-2 type

Finally the methyl protons bein chemically same would appear at the same place- 1 type

Summing them together, ideally there should be 9 different signals one can expect in the NMR spectra. 

2. Diastereotopic protons are those protons which are chemically non equivalent and  each produce distinct chemical shifts. Usually, the CH2 protons are considered as Diastereotopic protons. In this structure H10 and H11 are two diastereotopic protons. 

3. ppm shift of each chemically equivalent proton

H2, H3, H7 and H8 --> 7.2 ppm

H1, H4, H6 and H9 --> 7.3 ppm

H15, H16 and H17 --> 2.5 ppm

 

    

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