Question 22 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. dilute HBr Mechanism A: 8 Br CH2 nucleophilic attack H..O HCH2 proton transfer :O H proton Br dilute H-Br: Br transfer Mechanism B: proton transfer dilute H-Br: tertiary carbocation hydrogen migration (rearrangement) HCH3 secondary carbocation nucleophilic attack H HCH3 tertiary carbocation Mechanism C: :Br: :O nucleophilic attack :Br CH3 nucleophilic dilute H-Br: attack === proton transfer elimination primary carbanion Br: H-Br: dilute H-Br: proton disassosiation proton transfer Br :Br-H Mechanism D: dilute H-Br: O B ос OD secondary carbanion Br proton transfer CH2 H CH3 H-Br: dilute H-Br: Η H-Br: proton transfer elimination nucleophilic attack proton disassosiation tertiary carbocation H H CH3 Θ Br: Br Br
Question 22 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. dilute HBr Mechanism A: 8 Br CH2 nucleophilic attack H..O HCH2 proton transfer :O H proton Br dilute H-Br: Br transfer Mechanism B: proton transfer dilute H-Br: tertiary carbocation hydrogen migration (rearrangement) HCH3 secondary carbocation nucleophilic attack H HCH3 tertiary carbocation Mechanism C: :Br: :O nucleophilic attack :Br CH3 nucleophilic dilute H-Br: attack === proton transfer elimination primary carbanion Br: H-Br: dilute H-Br: proton disassosiation proton transfer Br :Br-H Mechanism D: dilute H-Br: O B ос OD secondary carbanion Br proton transfer CH2 H CH3 H-Br: dilute H-Br: Η H-Br: proton transfer elimination nucleophilic attack proton disassosiation tertiary carbocation H H CH3 Θ Br: Br Br
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Transcribed Image Text:Question 22
Select correct and most relevant mechanism for each of the following reaction.
Hint: Review Chapter 11.4.
dilute HBr
Mechanism A:
Mechanism B:
8
Br
CH2
nucleophilic attack
H..O
HCH2
proton transfer
H proton
transfer
Br dilute H-Br:
Br
proton transfer
tertiary
carbocation
hydrogen migration
(rearrangement)
HCH3
H
dilute H-Br:
secondary
carbocation
nucleophilic attack
H
HCH3
tertiary
carbocation
Mechanism C:
:Br:
:O
nucleophilic
attack
:Br
CH3
nucleophilic
dilute H-Br:
:Br:
attack
=
proton transfer
elimination
primary
carbanion
:Br:
H-Br:
dilute H-Br:
proton
disassosiation
proton transfer
Br
:Br-H
Mechanism D:
dilute H-Br:
A
O B
ос
OD
secondary
carbanion
Br
proton transfer
CH2
H CH3
H-Br:
dilute H-Br:
Η
H-Br:
proton transfer
elimination
proton
disassosiation
nucleophilic attack
tertiary
carbocation
H
H CH3
Θ
Br:
Br
Br
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