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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