Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Br dilute HBr Mechanism A: H. CH2 nucleophilic attack HO HCH2 proton transfer H proton Br dilute H-Br: Br transfer Mechanism B: proton transfer dilute H-Br: tertiary carbocation hydrogen migration (rearrangement) HOCH3 H HCH3 = secondary carbocation Mechanism C: tertiary carbocation nucleophilic attack nucleophilic attack CH3 nucleophilic attack dilute H-Br: proton transfer primary carbanion Br: elimination H-Br: dilute H-Br: proton disassosiation Mechanism D: dilute H-Br: A B C proton transfer Br Br :Br-H secondary carbanion ..☺ CH2 proton transfer Н H CH3 H-Br: dilute H-Br: H-Br: proton transfer elimination proton disassosiation nucleophilic attack tertiary carbocation H HCH3 Br

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
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.58P
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Question 22
Select correct and most relevant mechanism for each of the following reaction.
Hint: Review Chapter 11.4.
Br
dilute HBr
Mechanism A:
H.
CH2
Hproton
transfer
nucleophilic attack
H ..O
HCH2
proton transfer
Br dilute H-Br:
Br
Mechanism B:
proton transfer
tertiary
carbocation
hydrogen migration
(rearrangement)
HCH3
dilute H-Br:
Mechanism C:
secondary
carbocation
:Br:
nucleophilic attack
H
HCH3
Br
tertiary
carbocation
:Br:
nucleophilic
attack
nucleophilic
attack
CH3
dilute H-Br:
Η
proton transfer
elimination
primary
carbanion
O
:Br:
H-Br:
proton
disassosiation
proton transfer
Br
Br
dilute H-Br:
:Br:
:Br-H
Mechanism D:
dilute H-Br:
B
с
secondary
carbanion
proton transfer
H.
CH2
CH2
H
H CH3
H-Br:
dilute H-Br:
H-Br:
proton transfer
:Br:
elimination
proton
disassosiation
nucleophilic attack
tertiary
carbocation
H
H CH3
Br
:Br:
Transcribed Image Text:Question 22 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Br dilute HBr Mechanism A: H. CH2 Hproton transfer nucleophilic attack H ..O HCH2 proton transfer Br dilute H-Br: Br Mechanism B: proton transfer tertiary carbocation hydrogen migration (rearrangement) HCH3 dilute H-Br: Mechanism C: secondary carbocation :Br: nucleophilic attack H HCH3 Br tertiary carbocation :Br: nucleophilic attack nucleophilic attack CH3 dilute H-Br: Η proton transfer elimination primary carbanion O :Br: H-Br: proton disassosiation proton transfer Br Br dilute H-Br: :Br: :Br-H Mechanism D: dilute H-Br: B с secondary carbanion proton transfer H. CH2 CH2 H H CH3 H-Br: dilute H-Br: H-Br: proton transfer :Br: elimination proton disassosiation nucleophilic attack tertiary carbocation H H CH3 Br :Br:
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