
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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What would be the correct structure based on the following NMR data
Molecule formula: C8H8O2
- S:3.6ppm. Singlet,3H
- S:7.4ppm and 7.8 ppm doublet of doublets 4H total
-S:9.8ppm singlet,1H

Transcribed Image Text:Typical 'H Chemical Shifts
Type of Proton
Structure
Chemical Shift (ppm)
Alkyl groups
R3C-H
0.9 - 1.5
Vinyl (alkene)
C=C-H
4.6 – 5.9
Acetylene
C=C-H
2 - 3
Aromatic
Ar-H
6 - 8.5
Benzyl
Ar-C-H
2.2 - 3
Allyl and propargyl
C=C-CH3
1.7 – 2.5
Halides
Н-С-Х
2 - 4.5
Oxygen adjacent carbons
Н-С-ОН
3.4 - 4
Carbonyl adjacent carbons
H-C-COOR
1.9 – 2.7
Aldehyde hydrogen
R-CHO
9 - 10
Hydroxyl group
R-C-ОH
1- 5.5
Amino group
RNH2
1-5.5
Carboxylic acid hydrogen
Amides
RCOOH
10.5 -12
RNHCOR'
5-8.5
H-C-NO2
4.3 - 5.3
Nitro
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