1. The fragrant natural product anethole (C10H120) is obtained from anise by steam distillation. The proton NMR spectrum of the purified material follows. Expansions of each of the peaks are also shown, except for the singlet at 3.75 ppm. Deduce the structure of anethole, including stereochemistry, and interpret the spectrum.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
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Problem 22.10P: Addition of m-xylene to the strongly acidic solvent HF/SbF5 at 45C gives a new species, which shows...
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1. The fragrant natural product anethole (CioH12O) is obtained from anise by steam distillation.
The proton NMR spectrum of the purified material follows. Expansions of each of the peaks
are also shown, except for the singlet at 3.75 ppm. Deduce the structure of anethole, including
stereochemistry, and interpret the spectrum.
-300 MHz
10
6.40
6.35
630
6.25
1.90
1.85
1.80
(ppm)
6.15
6.10
6.05
6.00
9L'6061
1908.19
S189395
1892.39
90s-
- 551.49
Transcribed Image Text:1. The fragrant natural product anethole (CioH12O) is obtained from anise by steam distillation. The proton NMR spectrum of the purified material follows. Expansions of each of the peaks are also shown, except for the singlet at 3.75 ppm. Deduce the structure of anethole, including stereochemistry, and interpret the spectrum. -300 MHz 10 6.40 6.35 630 6.25 1.90 1.85 1.80 (ppm) 6.15 6.10 6.05 6.00 9L'6061 1908.19 S189395 1892.39 90s- - 551.49
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