When 2,2-dimethylcyclohexanol is treated with acid, 1,2-dimethylcyclohexene and iso- propylidenecyclopentane are the products obtained. Draw a detailed mechanism that explains this result. CH 3 CH3 CH3 H3O* CH3 OH CH3 CH3 1,2-dimethyl- isopropylidene- cyclopentane 2,2-dimethyl- cyclohexanol cyclohexene

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
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.23P
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When 2,2-dimethylcyclohexanol is treated with acid,
1,2-dimethylcyclohexene and iso-
propylidenecyclopentane are the products obtained. Draw a detailed mechanism that
explains this result.
CH 3
CH3
CH3
H3O*
CH3
OH
CH3
CH3
1,2-dimethyl-
isopropylidene-
cyclopentane
2,2-dimethyl-
cyclohexanol
cyclohexene
Transcribed Image Text:When 2,2-dimethylcyclohexanol is treated with acid, 1,2-dimethylcyclohexene and iso- propylidenecyclopentane are the products obtained. Draw a detailed mechanism that explains this result. CH 3 CH3 CH3 H3O* CH3 OH CH3 CH3 1,2-dimethyl- isopropylidene- cyclopentane 2,2-dimethyl- cyclohexanol cyclohexene
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