Question 35 The reaction below proceeds with the formation of four (4) products. Choose the mechanism below which best describes the following transformation. :OH HCI Mechanism A: :ÖH +.. :OH₂ loss of a leaving group methyl migration (rearrangement) CH₂ CH₂ H-CI: - H₂O proton transfer secondary carbocation tertiary carbocation resonance nucleophilic attack CH3 CH₂ Mechanism B: loss of a leaving group nucleophilic attack OH CH3 CH3 CH₂ methyl migration (rearrangement) Mechanism C: (он loss of a leaving group Mechanism D: tertiary carbocation nucleophilic attack OH methyl migration (rearrangement) secondary carbocation CH3 CH₂ secondary carbocation tertiary carbocation A resonance nucleophilic attack CH₂ CH3 © secondary carbocation loss of a leaving group OH₂ OH₂ :OH H-CI: CH₂ CH₂ :CI proton transfer nucleophilic attack -H₂O A ов ОС OD methyl migration (rearrangement) methyl migration (rearrangement) loss of a leaving group

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Please answer the following chemistry question
Question 35
The reaction below proceeds with the formation of four (4) products. Choose the mechanism below which best describes the following transformation.
:OH
HCI
Mechanism A:
:ÖH
+..
:OH₂
loss of a leaving group
methyl migration
(rearrangement)
CH₂
CH₂
H-CI:
- H₂O
proton transfer
secondary
carbocation
tertiary
carbocation
resonance
nucleophilic attack
CH3
CH₂
Mechanism B:
loss of a leaving group
nucleophilic attack
OH
CH3
CH3
CH₂
methyl migration
(rearrangement)
Mechanism C:
(он
loss of a leaving group
Mechanism D:
tertiary
carbocation
nucleophilic attack
OH
methyl migration
(rearrangement)
secondary carbocation
CH3
CH₂
secondary
carbocation
tertiary
carbocation A
resonance
nucleophilic attack
CH₂
CH3
©
secondary carbocation
loss of a leaving group
OH₂
OH₂
:OH
H-CI:
CH₂
CH₂
:CI
proton transfer
nucleophilic attack
-H₂O
A
ов
ОС
OD
methyl migration
(rearrangement)
methyl migration
(rearrangement)
loss of a leaving group
Transcribed Image Text:Question 35 The reaction below proceeds with the formation of four (4) products. Choose the mechanism below which best describes the following transformation. :OH HCI Mechanism A: :ÖH +.. :OH₂ loss of a leaving group methyl migration (rearrangement) CH₂ CH₂ H-CI: - H₂O proton transfer secondary carbocation tertiary carbocation resonance nucleophilic attack CH3 CH₂ Mechanism B: loss of a leaving group nucleophilic attack OH CH3 CH3 CH₂ methyl migration (rearrangement) Mechanism C: (он loss of a leaving group Mechanism D: tertiary carbocation nucleophilic attack OH methyl migration (rearrangement) secondary carbocation CH3 CH₂ secondary carbocation tertiary carbocation A resonance nucleophilic attack CH₂ CH3 © secondary carbocation loss of a leaving group OH₂ OH₂ :OH H-CI: CH₂ CH₂ :CI proton transfer nucleophilic attack -H₂O A ов ОС OD methyl migration (rearrangement) methyl migration (rearrangement) loss of a leaving group
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