Compound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown below. On treatment with excess H2/Pt (catalytic hydrogenation), X is converted to methylcyclohexane. Propose a structure for X and justify your reasoning by clearly labeling each carbon signal and write out the reaction. 200 180 160 140 120 100 80 60 40 20 8-

Organic Chemistry
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Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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Compound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown
below. On treatment with excess H2/Pt (catalytic hydrogenation), X is converted to
methylcyclohexane. Propose a structure for X and justify your reasoning by clearly labeling
each carbon signal and write out the reaction.
200
180
160
140
120
100
80
60
40
20
Transcribed Image Text:Compound X of the molecular formula C7H10 has the 13C NMR spectrum (5 signals) shown below. On treatment with excess H2/Pt (catalytic hydrogenation), X is converted to methylcyclohexane. Propose a structure for X and justify your reasoning by clearly labeling each carbon signal and write out the reaction. 200 180 160 140 120 100 80 60 40 20
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