:Br: A) The cation rapidly switches between two positions of the electrophile. The bromine atom moves to whichever position currently has the positive charge. B) Attack of the bromide on the cation repels the positive charge, flipping it to the other end of the double bond. Attack at the other end flips the charge back again. C) The cation is found simultaneously in two positions of the electrophile. The electrons from the negatively charged bromide are attracted to either of these cationic positions, forming a bromine- carbon bond. D) The cation is in equilibrium between two positions of the electrophile. The bromine atom attacks whichever position currently has the positive charge.

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.7: Sigmatropic Rearrangements
Problem 7P
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Choose the best explanation for the
proposed curved arrow mechanism for the
second step of an electrophilic addition
reaction of butadiene with HBr.
:Br
+
+
:Br:
Transcribed Image Text:Choose the best explanation for the proposed curved arrow mechanism for the second step of an electrophilic addition reaction of butadiene with HBr. :Br + + :Br:
Choose the best explanation for the
proposed curved arrow mechanism for the
second step of an electrophilic addition
reaction of butadiene with HBr.
:Br
+
+
:Br:
Transcribed Image Text:Choose the best explanation for the proposed curved arrow mechanism for the second step of an electrophilic addition reaction of butadiene with HBr. :Br + + :Br:
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