Propose structures for the compounds that would be expected to generate the following 1H NMR spectra. Calculate the degree of unsaturation of each compound and assign the protons to their respective peaks.
2) Propose structures for the compounds that would be expected to generate the following 1H NMR spectra. Calculate the degree of unsaturation of each compound and assign the protons to their respective peaks.
Homework Answers
A. formula = C10H13Br
degree of unsaturation = 4
NMR shows
7.25 ppm and 7.38 ppm as two doublets for 2H each. So benzene ring is symmetrically substituted
1.3 ppm (singlet, 9H) for tert-butyl group
So the structure is as below.
---
B. formula = C9H12
Degree of unsaturation = 4
NMR shows
1.2 ppm (doublet, 6H) for two CH3's next to CH
2.9 ppm for benzylic CH next to two CH3 and Ph
7.2 ppm (multiplet, 5H) for phenyl protons
So the structure is as shown below
---
C. formula = C6H4BrCl
degree of unsaturation = 4
NMR shows
7.2 ppm and 7.4 ppm as two doublets for 2H each. So benzene ring is symmetrically substituted
So the structure is as below.
---
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