Choose the best explanation for the proposed curved arrow mechanism for an electrophilic addition reaction of butadiene with HBr.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter8: Addition Via Carbocation
Section: Chapter Questions
Problem 9E
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Choose the best explanation for the proposed curved arrow mechanism for an electrophilic addition reaction of butadiene with HBr.

:Br:
Choose the best explanation for the proposed curved arrow mechanism for an
electrophilic addition reaction of butadiene with HBr.
H
Br:
A) The terminal carbon of the butadiene moves
toward the HBr to form a bond with the proton.
At the same time, the bromine atom moves
away. The result of this atomic movement is a
carbocation and a bromide anion.
B) The electronegative bromine draws the
electrons of the H-Br bond toward it, resulting in
a fully ionized proton and bromide ion. The
proton is donated to the butadiene, resulting in
a cation on the secondary position.
C) HBr donates a proton to the conjugated pi
bond of butadiene, leading to formation of a
delocalized carbocation. Donation of the proton
leaves behind a bromide ion.
D) Electrons are attracted from the pi bond to
the acidic hydrogen of the electrophile, leading
to formation of a carbocation. The electrons of
the H-Br bond become a lone pair on the
bromide ion.
Transcribed Image Text::Br: Choose the best explanation for the proposed curved arrow mechanism for an electrophilic addition reaction of butadiene with HBr. H Br: A) The terminal carbon of the butadiene moves toward the HBr to form a bond with the proton. At the same time, the bromine atom moves away. The result of this atomic movement is a carbocation and a bromide anion. B) The electronegative bromine draws the electrons of the H-Br bond toward it, resulting in a fully ionized proton and bromide ion. The proton is donated to the butadiene, resulting in a cation on the secondary position. C) HBr donates a proton to the conjugated pi bond of butadiene, leading to formation of a delocalized carbocation. Donation of the proton leaves behind a bromide ion. D) Electrons are attracted from the pi bond to the acidic hydrogen of the electrophile, leading to formation of a carbocation. The electrons of the H-Br bond become a lone pair on the bromide ion.
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