Problems 511 12.08 Treatment of compound C (molecular formula CoH120) with PCC affords D (molecular formula C,H100). Use the 'H NMR and IR spectra of D to determine the structures of both C and D. IR of D H NMR of D 100 5 H 1H 2 H 2 H 50 11 10 9. 4000 3500 3000 2500 2000 1500 1000 500 nnm % Transmittance

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
Chapter13: Nuclear Magnetic Resonance Spectroscopy
Section: Chapter Questions
Problem 13.17P: Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each...
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can you solve 12.68. findng structures from IR and NMR 

Problems
511
12.68
.08 Treatment of compound C (molecular formula C3H120) with PCC affords D (molecular formula C3H100). Use the 'H NMR and
IR spectra of D to determine the structures of both C and D.
IR of D
100
H NMR of D
5 H
1 H
2 H
2 H
50
11
10
8 7
6.
4.
3 2
1 0
4000
3500
3000
2500
2000
1500
1000
500
ppm
Wavenumber (cm)
Challenge Problems
The Birch reduction is a dissolving metal reaction that converts substituted benzenes to cyclohexa-1,4-dienes using Li and
liquid ammonia in the presence of an alcohol. Draw a stepwise mechanism for the following Birch reduction.
12.69
Li
OCH3
OCH3
NH3
CH3CH,OH
12.70 Identify the starting material in the following reaction sequence.
HO
[1] OsO4
[2] NaH
% Transmittance
Transcribed Image Text:Problems 511 12.68 .08 Treatment of compound C (molecular formula C3H120) with PCC affords D (molecular formula C3H100). Use the 'H NMR and IR spectra of D to determine the structures of both C and D. IR of D 100 H NMR of D 5 H 1 H 2 H 2 H 50 11 10 8 7 6. 4. 3 2 1 0 4000 3500 3000 2500 2000 1500 1000 500 ppm Wavenumber (cm) Challenge Problems The Birch reduction is a dissolving metal reaction that converts substituted benzenes to cyclohexa-1,4-dienes using Li and liquid ammonia in the presence of an alcohol. Draw a stepwise mechanism for the following Birch reduction. 12.69 Li OCH3 OCH3 NH3 CH3CH,OH 12.70 Identify the starting material in the following reaction sequence. HO [1] OsO4 [2] NaH % Transmittance
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