Compound Molecular C5H100 formula: 1728, 2791, and 2700 cm-1 IR absorptions at 1H NMR data: 1.08 (singlet, 9 H) and 9.48 (singlet, 1 H) ppm Compound Molecular С10Н120 B formula: 1686 cm-1 IR absorption at 1H NMR data: 1.21 (triplet, 3 H), 2.39 (singlet, 3 H), 2.95 (quartet, 2 H), 7.24 (doublet, 2 H), and 7.85 (doublet, 2 H) ppm Compound Molecular C10H120 formula: 1719 cm-1 IR absorption at 1H NMR data: 1.02 (triplet, 3 H), 2.45 (quartet, 2 H), 3.67 (singlet, 2 H), and 7.06–7.48 (multiplet, 5 H) ppm

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 87AP: The proton NMR spectrum for a compound with formula C10H12O2 is shown below. The infrared spectrum...
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Use the 1H NMR and IR data to determine the structure of each compound.

Compound
Molecular
C5H100
formula:
1728, 2791, and 2700 cm-1
IR absorptions at
1H NMR data:
1.08 (singlet, 9 H) and 9.48
(singlet, 1 H) ppm
Compound
Molecular
С10Н120
B
formula:
1686 cm-1
IR absorption at
1H NMR data:
1.21 (triplet, 3 H), 2.39 (singlet,
3 H), 2.95 (quartet, 2 H), 7.24
(doublet, 2 H), and 7.85
(doublet, 2 H) ppm
Compound
Molecular
C10H120
formula:
1719 cm-1
IR absorption at
1H NMR data:
1.02 (triplet, 3 H), 2.45 (quartet,
2 H), 3.67 (singlet, 2 H), and
7.06–7.48 (multiplet, 5 H) ppm
Transcribed Image Text:Compound Molecular C5H100 formula: 1728, 2791, and 2700 cm-1 IR absorptions at 1H NMR data: 1.08 (singlet, 9 H) and 9.48 (singlet, 1 H) ppm Compound Molecular С10Н120 B formula: 1686 cm-1 IR absorption at 1H NMR data: 1.21 (triplet, 3 H), 2.39 (singlet, 3 H), 2.95 (quartet, 2 H), 7.24 (doublet, 2 H), and 7.85 (doublet, 2 H) ppm Compound Molecular C10H120 formula: 1719 cm-1 IR absorption at 1H NMR data: 1.02 (triplet, 3 H), 2.45 (quartet, 2 H), 3.67 (singlet, 2 H), and 7.06–7.48 (multiplet, 5 H) ppm
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