Identify the compound A (C,H,0) with the proton NMR spectrum shown. Compound A has IR absorptions at 3200 to 3600 cm- (strong, broad), 1676 cm-1 (weak), and 965 cm-', and also has 13C NMR absorptions (attached protons in parentheses) at ô 17.5 (3), ô 23.3 (3), 8 68.8 (1), ô 125.5 (1), and ô 135.5 (1). Compound A may be resolved into enantiomers; draw one molecule of A, omitting wedge and dash bonds. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 ЗН 6.2 Hz 6.3 Hz 6.3 Hz 6.2 Hz _6.3 Hz 3H 1H 2H 1H disappears on D20 shake'

Organic Chemistry
8th Edition
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Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.20P
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please draw a compound given the following info

Identify the compound A (C,H,0) with the proton NMR spectrum shown. Compound A has IR absorptions at 3200 to 3600
cm-1 (strong, broad), 1676 cm-1 (weak), and 965 cm-!, and also has "C NMR absorptions (attached protons in parentheses)
at ô 17.5 (3), 8 23.3 (3), 8 68.8 (1), 8 125.5 (1), and ô 135.5 (1). Compound A may be resolved into enantiomers; draw one
molecule of A, omitting wedge and dash bonds.
chemical shift, Hz
2400
2100
1800
1500
1200
900
600
300
6.2 Hz
ЗН
|6.3 Hz
6.3 Hz
6.2-
Hz
_6.3
Hz
3H
1H
2H
1H
disappears
on D20 shake'
Transcribed Image Text:Identify the compound A (C,H,0) with the proton NMR spectrum shown. Compound A has IR absorptions at 3200 to 3600 cm-1 (strong, broad), 1676 cm-1 (weak), and 965 cm-!, and also has "C NMR absorptions (attached protons in parentheses) at ô 17.5 (3), 8 23.3 (3), 8 68.8 (1), 8 125.5 (1), and ô 135.5 (1). Compound A may be resolved into enantiomers; draw one molecule of A, omitting wedge and dash bonds. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 6.2 Hz ЗН |6.3 Hz 6.3 Hz 6.2- Hz _6.3 Hz 3H 1H 2H 1H disappears on D20 shake'
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