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. CH3 H3O+ CH3 CH3 CH3 OH CH3 CH3 2,2-dimethyl- cyclohexanol 1,2-dimethyl- isopropylidene- cyclopentane cyclohexene

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 27MP
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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.
CH3
H3O+
CH3
CH3
CH3
OH
CH3
CH3
2,2-dimethyl-
cyclohexanol
1,2-dimethyl-
isopropylidene-
cyclopentane
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. CH3 H3O+ CH3 CH3 CH3 OH CH3 CH3 2,2-dimethyl- cyclohexanol 1,2-dimethyl- isopropylidene- cyclopentane cyclohexene
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