1. In both the starting material and product the chemical shift of the hydroxyl proton is approximately 13 ppm. Table 22.2 in your "Techniques in Organic Chemistry" textbook gives 4.0 - 8.0 ppm as the typical range for phenolic protons. Explain this apparent discrepancy. Hint: Think about the solvent the NMR spectrum was run in...
1. In both the starting material and product the chemical shift of the hydroxyl proton is approximately 13 ppm. Table 22.2 in your "Techniques in Organic Chemistry" textbook gives 4.0 - 8.0 ppm as the typical range for phenolic protons. Explain this apparent discrepancy. Hint: Think about the solvent the NMR spectrum was run in...
Chemistry
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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...
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Transcribed Image Text:c2013902onno Part 5 •
Spectrometric Methods
TABLE 22.2
Characteristic 'H NMR chemical shifts in CDCI.
Chemical shift (6, ppm)
punoduwoɔ
0.0
TMS
0.8-1.9
Alkanes (C-C-H)
0.6-4.5
Amines (C-N-H)
Alcohols (C-O-H)
Alkenesa (C=C-C-H)
Alkynes (C=C-H)
Carbonyl compounds (O=C-C-H)
Halides (X-C-H)
Aromatic compoundsb (Ar-C-H)
Alcohols, esters, ethers (O-C-H)
Alkenes (C=C-H)
Phenols (Ar-O-H)
Amides (O=C-N-H)
Aromatic compounds (Ar-H)
Aldehydes (O=C-H)
Carboxylic acids (O=C-O-H)
0.5-5.0
1.5-2.6
1.7-3.1
1.9-3.3
2.1-4.5
2.2-3.0
3.2-5.3
4.5-8.5
4.0-8.0
5.5-9.5
6.5-9.0
9.5-10.5
9.7-12.5
a. Allylic protons.
b. Benzylic protons.
EXERCISE
The 'H NMR spectrum of (CH,),C(OH)C=C-H shown in Figure 22. one
three peaks. Determine the chemical shift of each peak and assign each
to the appropriate proton(s).
Answer: The respective ch
Transcribed Image Text:1. In both the starting material and product the chemical shift of the hydroxyl proton is
approximately 13 ppm. Table 22.2 in your “Techniques in Organic Chemistry" textbook gives 4.0
- 8.0 ppm as the typical range for phenolic protons. Explain this apparent discrepancy. Hint: Think
about the solvent the NMR spectrum was run in.….
Expert Solution
Step 1
Electron withdrawing group and intramolecular hydrogen bond interaction make a proton deshielded and thus results higher chemical shift.
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