In the expanded region of 1H NMR for 4-t-butylcyclohexanols, the peak at 4.05 ppm integrates to 1.0 while the peak at 3.52 ppm integrates to 2.52. Please use this information to calculate the percentage of each isomer in the sample.  QUESTION- Based on the 1H NMR, Please explain the cis vs. trans product ratio. Is it consistent with the expected results? Why or why not?

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
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In the expanded region of 1H NMR for 4-t-butylcyclohexanols, the peak at 4.05 ppm integrates to 1.0 while the peak at 3.52 ppm integrates to 2.52. Please use this information to calculate the percentage of each isomer in the sample. 

QUESTION- Based on the 1H NMR, Please explain the cis vs. trans product ratio. Is it consistent with the expected results? Why or why not?

 

HO
4.05
х
1.00
7.5
HO
80
7.0
H C
75
6.5
CH₂
CH3
71.12
70
от
CH3
3.70
6.0
65.80
65
смим
edhin
тамирније
3.65 3.60 3.55 3.50 3.45 3.40
5.5
CH3
60
2.52
55
5.0
50
4.5
47.21
48 07
45
4.0
40
1.0
3.5
0.9
36.07
35
0.8
3.0
33.40
32.27
30
2.5
27.66
25.64
25
2.0
20.93
20
1.5
15
1.0
10
0.5
5
----
0.0
0
-5
Transcribed Image Text:HO 4.05 х 1.00 7.5 HO 80 7.0 H C 75 6.5 CH₂ CH3 71.12 70 от CH3 3.70 6.0 65.80 65 смим edhin тамирније 3.65 3.60 3.55 3.50 3.45 3.40 5.5 CH3 60 2.52 55 5.0 50 4.5 47.21 48 07 45 4.0 40 1.0 3.5 0.9 36.07 35 0.8 3.0 33.40 32.27 30 2.5 27.66 25.64 25 2.0 20.93 20 1.5 15 1.0 10 0.5 5 ---- 0.0 0 -5
NMR Spectra
The 'H and ¹3C NMR spectra of 4-t-butylcyclohexanone, your starting material, are shown
below. The ¹H NMR of your product is shown next with the resonances from 3 to 5 ppm
expanded so you can see them in detail and integrated. About the only useful absorption is the
singlet that integrates to 9. The ketone carbonyl is visible at 212 ppm in the ¹3C NMR spectrum
13,
however.
Ar
7.5
7.0
212.36
6.5
200
CH3
F
CH3
6.0
5.5
CH3
-CH3
CH3
-CH3
5.0
150
4.5
4.0
3.5
100
3.0
6.22
2.5
2.0
3.04
50
1.5
41.31
46.71
9.00
32.46
1.0
27.61
0.5
0
ון
0.0
Transcribed Image Text:NMR Spectra The 'H and ¹3C NMR spectra of 4-t-butylcyclohexanone, your starting material, are shown below. The ¹H NMR of your product is shown next with the resonances from 3 to 5 ppm expanded so you can see them in detail and integrated. About the only useful absorption is the singlet that integrates to 9. The ketone carbonyl is visible at 212 ppm in the ¹3C NMR spectrum 13, however. Ar 7.5 7.0 212.36 6.5 200 CH3 F CH3 6.0 5.5 CH3 -CH3 CH3 -CH3 5.0 150 4.5 4.0 3.5 100 3.0 6.22 2.5 2.0 3.04 50 1.5 41.31 46.71 9.00 32.46 1.0 27.61 0.5 0 ון 0.0
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