Like alkenes, conjugated dienes can be prepared by elimination reactions. Draw a stepwise mechanism for the acid-catalyzed dehydration of 3-methylbut-2-en-1-ol [(CH3)2C=CHCH2OH] to isoprene [CH2=C(CH3)CH=CH2].

Like alkenes, conjugated dienes can be prepared by elimination reactions. Draw a stepwise mechanism for the acid-catalyzed dehydration of 3-methylbut-2-en-1-ol [(CH3)2C=CHCH2OH] to isoprene [CH2=C(CH3)CH=CH2].

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 20.42P: Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide...

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Like alkenes, conjugated dienes can be prepared by elimination reactions. Draw a stepwise mechanism for the acid-catalyzed dehydration of 3-methylbut-2-en-1-ol [(CH₃)₂C=CHCH₂OH] to isoprene [CH₂=C(CH₃)CH=CH₂].

Definition Definition Organic compounds that contain at least one double bond between carbon-carbon atoms. The general molecular formula for alkenes with one double bond is C n H 2n .

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