For the following mechanism, select the order of arrow pushing patterns that would be needed to accomplish each step. CH₂ +H-OⓇ цасно + CH₂ H-OⓇ CH₂OH 1 + CH₂OH + CH₂ CH₂OH 1) Nucleophilic Attack; 2) Proton Transfer; 3) Loss of a Leaving Group; 4) Proton Transfer 1) Proton Transfer; 2) Carbocation Rearrangement; 3) Nucleophilic Attack; 4) Proton Transfer 1) Proton Transfer; 2) Loss of a Leaving Group; 3) Carbocation Rearrangement; 4) Proton Transfer 1) Proton Transfer; 2) Nucleophilic Attack 1) Proton Transfer; 2) Nucleophilic Attack; 3) Proton Transfer

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 30MP: The carbocation electrophile in a Friede1-Crafts reaction can be generated by an alternate means...
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F1
6.9 Combining the Patterns of Arrow Pushing
For the following mechanism, select the order of arrow pushing patterns that would be needed to accomplish each step.
CH₂
u.
·Ų.
+
2
+H-0
F2
Save for Later
W
u
H
#
3
80
F3
-CH3
E
+
O 1) Nucleophilic Attack; 2) Proton Transfer; 3) Loss of a Leaving Group; 4) Proton Transfer
1) Proton Transfer; 2) Carbocation Rearrangement; 3) Nucleophilic Attack; 4) Proton Transfer
1) Proton Transfer; 2) Loss of a Leaving Group; 3) Carbocation Rearrangement; 4) Proton Transfer
1) Proton Transfer; 2) Nucleophilic Attack
1) Proton Transfer; 2) Nucleophilic Attack; 3) Proton Transfer
$
4
H-OⓇ
H
CH3
000
000
F4
R
%
LO
CH₂OH
5
-
F5
T
^
CH₂
6
MacBook Air
F6
+ CH₂OH
Y
+ CH₂OH
&
7
F7
U
8
DII
FB
(
9
F9
Submit Answ
0
F10
Transcribed Image Text:F1 6.9 Combining the Patterns of Arrow Pushing For the following mechanism, select the order of arrow pushing patterns that would be needed to accomplish each step. CH₂ u. ·Ų. + 2 +H-0 F2 Save for Later W u H # 3 80 F3 -CH3 E + O 1) Nucleophilic Attack; 2) Proton Transfer; 3) Loss of a Leaving Group; 4) Proton Transfer 1) Proton Transfer; 2) Carbocation Rearrangement; 3) Nucleophilic Attack; 4) Proton Transfer 1) Proton Transfer; 2) Loss of a Leaving Group; 3) Carbocation Rearrangement; 4) Proton Transfer 1) Proton Transfer; 2) Nucleophilic Attack 1) Proton Transfer; 2) Nucleophilic Attack; 3) Proton Transfer $ 4 H-OⓇ H CH3 000 000 F4 R % LO CH₂OH 5 - F5 T ^ CH₂ 6 MacBook Air F6 + CH₂OH Y + CH₂OH & 7 F7 U 8 DII FB ( 9 F9 Submit Answ 0 F10
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