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...
icon
Related questions
Question
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
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
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 3 steps with 1 images

Blurred answer
Knowledge Booster
Designing a Synthesis
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY