Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Mechanism A: nucleophilic attack proton transfer CH₂ 5 Jy g H proton Br dilute H-Br: transfer = Mechanism B: dilute HBr Mechanism C: proton transfer nucleophilic attack H CH3 H CH3 Br 5-8-8-8 z z :Br = dilute H-Br: dilute H-Br: OA O Mechanism D: B nucleophilic attack dilute H-Br: = Br secondary carbocation proton disassosiation CH₂ primary carbanion Br: H.O HCH₂ tertiary carbocation hydrogen migration (rearrangement) proton disassosiation dilute H-Br: proton transfer H-Br: ** elimination H H. Br: CH₂ H H-Br: + tertiary carbocation proton transfer CH₂ elimination H-Br: proton transfer, Br nucleophilic attack Br-H secondary carbanion proton transfer Br dilute H-Br: Bri nucleophilic attack = H H H H₂ CH3 .Br Br CH3 tertiary carbocation
Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. Mechanism A: nucleophilic attack proton transfer CH₂ 5 Jy g H proton Br dilute H-Br: transfer = Mechanism B: dilute HBr Mechanism C: proton transfer nucleophilic attack H CH3 H CH3 Br 5-8-8-8 z z :Br = dilute H-Br: dilute H-Br: OA O Mechanism D: B nucleophilic attack dilute H-Br: = Br secondary carbocation proton disassosiation CH₂ primary carbanion Br: H.O HCH₂ tertiary carbocation hydrogen migration (rearrangement) proton disassosiation dilute H-Br: proton transfer H-Br: ** elimination H H. Br: CH₂ H H-Br: + tertiary carbocation proton transfer CH₂ elimination H-Br: proton transfer, Br nucleophilic attack Br-H secondary carbanion proton transfer Br dilute H-Br: Bri nucleophilic attack = H H H H₂ CH3 .Br Br CH3 tertiary carbocation
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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:Select correct and most relevant mechanism for each of the following reaction.
Hint: Review Chapter 11.4.
Mechanism A:
nucleophilic attack proton transfer
H.O
HCH₂
6-8=8²²²6
tertiary
carbocation
hydrogen migration
(rearrangement)
H CH3
H
Mechanism B:
dilute HBr
Mechanism C:
dilute H-Br:
OA
O
O
Mechanism D:
B
dilute H-Br:
C
D
dilute H-Br:
=
CH₂
nucleophilic
attack
Br
H proton
proton transfer
transfer
secondary
carbocation
proton
disassosiation
CH₂
primary
carbanion
Br
=
dilute H-Br:
proton
disassosiation
proton transfer
H-Br:
elimination
H.
Br:
CH₂
H
H CH3
H-Br:
+
tertiary
carbocation
proton transfer
Br dilute H-Br:
nucleophilic attack
:Br
CH₂
elimination
H-Br:
proton transfer,
Br
Br
Br-H
secondary
carbanion
proton transfer
nucleophilic
attack
dilute H-Br:
Bri
nucleophilic attack
=
Br
Br
H
H CH3
H
H₂ CH3
.Br
tertiary
carbocation
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