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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

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
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter23: Carbonyl Condensation Reactions
Section23.SE: Something Extra
Problem 73AP
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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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