When 1-methoxy-2-methylpropene is treated with HCI, the major product is 1-chloro-1-methoxy-2-methylpropane. Although this reaction proceeds via an ionic mechanism, the Cl is ultimately positioned at the less substituted carbon. Draw a mechanism that is consistent with this outcome and then explain why the less substituted carbocation intermediate is more stable in this case. HCI 1-Methoxy-2-methylpropene 1-Chloro-1-methoxy-2-methylpropane
When 1-methoxy-2-methylpropene is treated with HCI, the major product is 1-chloro-1-methoxy-2-methylpropane. Although this reaction proceeds via an ionic mechanism, the Cl is ultimately positioned at the less substituted carbon. Draw a mechanism that is consistent with this outcome and then explain why the less substituted carbocation intermediate is more stable in this case. HCI 1-Methoxy-2-methylpropene 1-Chloro-1-methoxy-2-methylpropane
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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.50P
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