Question 21 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. dilute HCI Mechanism A: proton disassosiation dilute H-CI: H3C CH3 :CI: nucleophilic attack H&C:CI: :CI: CH3 proton transfer :0 methyl migration and (rearrangement) Mechanism B: proton transfer secondary carbanion nucleophilic attack and methyl migration (rearrangement) Θ :CI: Θ H3C CH3 :CI: dilute H-CI: Mechanism C: proton transfer dilute H-CI: secondary carbocation Mechanism D: H₂C CH3 secondary carbocation methyl migration (rearrangement) nucleophilic attack H3C CH3 tertiary carbocation nucleophilic attack nucleophilic attack CI: CH3 CH3 :0 : CH3 tertiary carbocation secondary carbocation secondary carbanion proton transfer methyl disassosiation dilute H-CI: proton disassosiation A B C OD

Question 21 Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. dilute HCI Mechanism A: proton disassosiation dilute H-CI: H3C CH3 :CI: nucleophilic attack H&C:CI: :CI: CH3 proton transfer :0 methyl migration and (rearrangement) Mechanism B: proton transfer secondary carbanion nucleophilic attack and methyl migration (rearrangement) Θ :CI: Θ H3C CH3 :CI: dilute H-CI: Mechanism C: proton transfer dilute H-CI: secondary carbocation Mechanism D: H₂C CH3 secondary carbocation methyl migration (rearrangement) nucleophilic attack H3C CH3 tertiary carbocation nucleophilic attack nucleophilic attack CI: CH3 CH3 :0 : CH3 tertiary carbocation secondary carbocation secondary carbanion proton transfer methyl disassosiation dilute H-CI: proton disassosiation A B C OD

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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