13C NMR spectrum 20 180 160 140 120 100 80 60 40 20 CDS-00-327 ppm O singly substituted O para substituted O 1,4-Disubstituted O 1,2-Disubstituted O 1,3-Disubstituted O triply substituted

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
Problem 11CTQ
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Shown below are three isomers of a disubstituted benzene ring. The 1H NMR and 13C NMR spectra are also shown below for ONE of these isomers. Identify which isomer is producing these spectra? 

Hint: Consider the number of chemically equivalent hydrogen and carbon environments in each structure and the number of signals expected for each.

In practise, overlapping of signals may occur if two or more hydrogen environments (or carbon environments for 13C NMR) are very similar to one another. This is often seen for aromatic signals in particular.

13C NMR spectrum
200
180
160
140
120
100
80
60
40
20
CDS-00-327
ppm
O singly substituted
para substituted
O 1,4-Disubstituted
O 1,2-Disubstituted
O 1,3-Disubstituted
O triply substituted
Transcribed Image Text:13C NMR spectrum 200 180 160 140 120 100 80 60 40 20 CDS-00-327 ppm O singly substituted para substituted O 1,4-Disubstituted O 1,2-Disubstituted O 1,3-Disubstituted O triply substituted
Shown below are three isomers of a disubstituted benzene ring. The 'H NMR and 13C NMR spectra are also shown below for ONE of these isomers. Identify which isomer is producing these spectra?
Hint: Consider the number of chemically equivalent hydrogen and carbon environments in each structure and the number of signals expected for each.
In practise, overlapping of signals may occur if two or more hydrogen environments (or carbon environments for 1C NMR) are very similar to one another. This is often seen for aromatic signals in particular.
CH3
CH
CH.
CH3
CH3
CH3
1,2-disubstituted
1,3-disubstituted
1.4-disubstituted
1H NMR spectrum
2 overlapping signals
9
8.
7
6
4
3.
2
1
Transcribed Image Text:Shown below are three isomers of a disubstituted benzene ring. The 'H NMR and 13C NMR spectra are also shown below for ONE of these isomers. Identify which isomer is producing these spectra? Hint: Consider the number of chemically equivalent hydrogen and carbon environments in each structure and the number of signals expected for each. In practise, overlapping of signals may occur if two or more hydrogen environments (or carbon environments for 1C NMR) are very similar to one another. This is often seen for aromatic signals in particular. CH3 CH CH. CH3 CH3 CH3 1,2-disubstituted 1,3-disubstituted 1.4-disubstituted 1H NMR spectrum 2 overlapping signals 9 8. 7 6 4 3. 2 1
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