The hydroboration of methylphenylcateylene (1-phenyl-1-propyne) with 9-Borabicyclo[3.3.1]nonane could, in theory, lead to four distinct products. Under carefully controlled reaction conditions, however, only one major product is observed. However, for all four possibilities, simple ¹H NMR shows signals for a methyl group, a vinyl proton and a phenyl ring, as well as the bicylcononane ring. An NOE experiment is performed showing enchancement of the methyl and vinyl proton signals on irradiation of the bicyclononane fragment. Likewise, irradiation of the vinyl resonance shows an enhancement of the signals for both the bicyclononane signals and the phenyl ring peaks. Which isomer is formed? Me Me Ą Select one: A. Isomer A B. Isomer B C. Isomer C D. Isomer D R₂B Ph BR₂ Me C Ph R₂B BR₂ H

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The hydroboration of methylphenylcateylene (1-phenyl-1-propyne) with 9-Borabicyclo[3.3.1]nonane could, in theory, lead to four distinct products. Under carefully controlled reaction conditions,
however, only one major product is observed. However, for all four possibilities, simple ¹H NMR shows signals for a methyl group, a vinyl proton and a phenyl ring, as well as the bicylcononane ring.
An NOE experiment is performed showing enchancement of the methyl and vinyl proton signals on irradiation of the bicyclononane fragment. Likewise, irradiation of the vinyl resonance shows an
enhancement of the signals for both the bicyclononane signals and the phenyl ring peaks. Which isomer is formed?
Me
H
Me
HB4
Select one:
A. Isomer A
B. Isomer B
C. Isomer C
D. Isomer D
R₂B
Ph
H
H
BR₂
Me
A
C
Ph
R₂B
Ph
B
BR₂
H
Me
D
Transcribed Image Text:The hydroboration of methylphenylcateylene (1-phenyl-1-propyne) with 9-Borabicyclo[3.3.1]nonane could, in theory, lead to four distinct products. Under carefully controlled reaction conditions, however, only one major product is observed. However, for all four possibilities, simple ¹H NMR shows signals for a methyl group, a vinyl proton and a phenyl ring, as well as the bicylcononane ring. An NOE experiment is performed showing enchancement of the methyl and vinyl proton signals on irradiation of the bicyclononane fragment. Likewise, irradiation of the vinyl resonance shows an enhancement of the signals for both the bicyclononane signals and the phenyl ring peaks. Which isomer is formed? Me H Me HB4 Select one: A. Isomer A B. Isomer B C. Isomer C D. Isomer D R₂B Ph H H BR₂ Me A C Ph R₂B Ph B BR₂ H Me D
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