Your task: Determine which isomer (trans or cis) correspond to the 2 methylene peaks at 3.1 ppm and 3.8 ppm

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Your task:
Determine which isomer (trans or cis)
correspond to the 2 methylene peaks at 3.1
ppm and 3.8 ppm
• You will have to calculate the coupling
constant for both methylene and assign
them to the red proton below
он
H OH
H₂
8. &
cis
trans
Coupling pattern: doublet of
triplet
You will look for the original
triplet that split into a
doublet
Use peaks 1 and 3
Coupling
constant
Axial Hs
11₂
OH
trans
CH₂
9-12 Hz
triplet
How to determine the isomer via coupling constant
OH
H
doublet
CH
FIG. 36.1
The 20-spectrum
of a mixture of cand
2-metyyl
CH₂
HG.:
The MIMB
The 250-MH NMR spectrum
of a mixture of cle and
trace-3-methylcycl
The frequens of pas
1595039475
9448,942.2 and 135 H
respectively. The
of peaks to 11 are 791 2.
786.3.761.6,777.1,7716,
and 767, respectively
The frequencies of peaks
1 to 5 are 96.3, 947.5,
equatorial Hs
2-5 Hz
9448, 42.2 and 10
respectively. The
af peaks 6 to 11
7868, 781 777.1, 771.4.
and 757.4 Hr, respectively
Axial Hs
11₂
26 3.8
H₂
wha
4-7 Hz
Coupling constant:
smaller spacing
between each peak
سل
World
FPM
197
23
LD
HOH
cis
13
MIN
10
C1₂
equatorial Hs
as
4-7 Hz
• Assume the hydrogens for both cis
and trans will be in axial position (so
that methyl is equatorial)
Transcribed Image Text:Your task: Determine which isomer (trans or cis) correspond to the 2 methylene peaks at 3.1 ppm and 3.8 ppm • You will have to calculate the coupling constant for both methylene and assign them to the red proton below он H OH H₂ 8. & cis trans Coupling pattern: doublet of triplet You will look for the original triplet that split into a doublet Use peaks 1 and 3 Coupling constant Axial Hs 11₂ OH trans CH₂ 9-12 Hz triplet How to determine the isomer via coupling constant OH H doublet CH FIG. 36.1 The 20-spectrum of a mixture of cand 2-metyyl CH₂ HG.: The MIMB The 250-MH NMR spectrum of a mixture of cle and trace-3-methylcycl The frequens of pas 1595039475 9448,942.2 and 135 H respectively. The of peaks to 11 are 791 2. 786.3.761.6,777.1,7716, and 767, respectively The frequencies of peaks 1 to 5 are 96.3, 947.5, equatorial Hs 2-5 Hz 9448, 42.2 and 10 respectively. The af peaks 6 to 11 7868, 781 777.1, 771.4. and 757.4 Hr, respectively Axial Hs 11₂ 26 3.8 H₂ wha 4-7 Hz Coupling constant: smaller spacing between each peak سل World FPM 197 23 LD HOH cis 13 MIN 10 C1₂ equatorial Hs as 4-7 Hz • Assume the hydrogens for both cis and trans will be in axial position (so that methyl is equatorial)
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