You are asked to identify an unknown compound, which has the following analytical data: 8. 5 3 PPM Chemical Shift Integration Multiplicity 8.28 7.95 7.48 6.99 4.11 2.81 1.34 3 The peak at 8.28 ppm is found to disappear when the NMR sample is treated with D20 The IR spectrum of the unknown has the following key peaks; a sharp strong peak at 1680 cm a broad signal at 3250 cm The compound has a molecular weight of 213.66 You have been provided with 9 possible structures of the unknown compound.

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 13.28P
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Interpret the analytical data reported including reference to IR NMR chemical shifts integration and splitting patterns 

H.
N'
CI
NH2
Strucutre 2
Strucutre 1
Strucutre 3
H.
F.
N.
CI
NH,
Strucutre 4
Strucutre 5
Strucutre 6
CI
N.
H.
N.
CI
NH,
Cl
Strucutre 7
Strucutre 8
Strucutre 9
O:
ZI
Transcribed Image Text:H. N' CI NH2 Strucutre 2 Strucutre 1 Strucutre 3 H. F. N. CI NH, Strucutre 4 Strucutre 5 Strucutre 6 CI N. H. N. CI NH, Cl Strucutre 7 Strucutre 8 Strucutre 9 O: ZI
You are asked to identify an unknown compound, which has the following analytical
data:
8.
6.
4
PPM
3.
Chemical Shift
8.28
Integration
Multiplicity
1
7.95
7.48
1
d.
1
S
6.99
4.11
1
2
2.81
3
S
1.34
3
The peak at 8.28 ppm is found to disappear when the NMR sample is treated with
D20
The IR spectrum of the unknown has the following key peaks;
a sharp strong peak at 1680 cm-1
a broad signal at 3250 cm1
The compound has a molecular weight of 213.66
You have been provided with 9 possible structures of the unknown compound.
Transcribed Image Text:You are asked to identify an unknown compound, which has the following analytical data: 8. 6. 4 PPM 3. Chemical Shift 8.28 Integration Multiplicity 1 7.95 7.48 1 d. 1 S 6.99 4.11 1 2 2.81 3 S 1.34 3 The peak at 8.28 ppm is found to disappear when the NMR sample is treated with D20 The IR spectrum of the unknown has the following key peaks; a sharp strong peak at 1680 cm-1 a broad signal at 3250 cm1 The compound has a molecular weight of 213.66 You have been provided with 9 possible structures of the unknown compound.
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