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: nucleophilic attack H₁C CH3 H₁C: CI: CI: CH3 proton transfer and :0 methyl migration (rearrangement) Mechanism B: proton transfer Q dilute H-CI: secondary carbanion nucleophilic attack and methyl migration (rearrangement) CI H3C CH3 Mechanism C: proton transfer dilute H-CI: secondary carbocation methyl migration (rearrangement) H3C CH3 nucleophilic attack :CI: y = y ð 8 4 8 Mechanism D: H₂C CH3 secondary carbocation tertiary carbocation nucleophilic attack nucleophilic attack :CI: Θ CH3 CH3 methyl disassosiation CH3 tertiary carbocation secondary carbocation proton disassosiation dilute H-CI: :CI: + A B CD secondary carbanion proton transfer CI:
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: nucleophilic attack H₁C CH3 H₁C: CI: CI: CH3 proton transfer and :0 methyl migration (rearrangement) Mechanism B: proton transfer Q dilute H-CI: secondary carbanion nucleophilic attack and methyl migration (rearrangement) CI H3C CH3 Mechanism C: proton transfer dilute H-CI: secondary carbocation methyl migration (rearrangement) H3C CH3 nucleophilic attack :CI: y = y ð 8 4 8 Mechanism D: H₂C CH3 secondary carbocation tertiary carbocation nucleophilic attack nucleophilic attack :CI: Θ CH3 CH3 methyl disassosiation CH3 tertiary carbocation secondary carbocation proton disassosiation dilute H-CI: :CI: + A B CD secondary carbanion proton transfer CI:
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 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:
H₁C CH3
nucleophilic attack
H₁C: CI:
:CI:
CH3
proton transfer
:0
and
methyl migration
(rearrangement)
Mechanism B:
proton transfer
Q
dilute H-CI:
secondary carbanion
nucleophilic attack and
methyl migration (rearrangement)
CI:
H3C CH3
Mechanism C:
proton transfer
dilute H-CI:
secondary
carbocation
methyl migration
(rearrangement)
H3C CH3
nucleophilic attack
:CI:
y = y 8 8 4 8
Mechanism D:
H&C CH3
2
methyl
disassosiation
dilute H-CI:
CH3
secondary
carbocation
tertiary
carbocation
proton
disassosiation
:CI: +
nucleophilic attack
tertiary
carbocation
:CI:
nucleophilic attack
Θ
6 6
secondary
carbocation
CH3
7
secondary
carbanion
proton transfer
CI:
CH3
с
ABCD
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