1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts. Which of the following correctly describes this new resonance structure? a) It has a double bond between carbons 3 and 4 b) It has a positive charge on carbon 2 c) It has a positive charge on carbon 4 d) It has a double bond between carbons 2 and 3

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
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.22P: Account for the fact that addition of HCl to 1-bromopropene gives exclusively...
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1,3-pentadiene reacts with HBr. When the double bond at the 3-position reacts, the hydrogen attaches to the 4-carbon, thus forming an allylic carbocation with delocalized electrons. This carbocation has another resonance structure. Because there are equal amounts of diene and hydrogen bromide, in which molecule only one of the double bonds reacts.

Which of the following correctly describes this new resonance structure?

a) It has a double bond between carbons 3 and 4

b) It has a positive charge on carbon 2

c) It has a positive charge on carbon 4

d) It has a double bond between carbons 2 and 3

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