The following two sets of reactions [(a) and (b)] show possibilities for arrow pushing in individual reaction steps. Identify which is wrong and explain why. Then using arrow pushing correctly, label which molecule is the nucleophile and which is the electrophile. (b) (a) H-CI: . .- :O: :Ö: H3C H3C CH3 C=N C-CH3 + :CI: H3C CH3 H3C CH2 H3C H3C ":C=N: H-CI: H3C I+ C-CH3 + :C: H3C H3C CH3 CH3 C=N: C-CH2 H3C > H3C H3C C=N:

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
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.59P
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The following two sets of reactions [(a) and (b)] show possibilities for arrow
pushing in individual reaction steps. Identify which is wrong and explain why.
Then using arrow pushing correctly, label which molecule is the nucleophile
and which is the electrophile.
(b)
(a)
H-CI:
. .-
:O:
:Ö:
H3C
H3C
CH3
C=N
C-CH3 + :CI:
H3C
CH3
H3C
CH2
H3C
H3C
":C=N:
H-CI:
H3C
I+
C-CH3 + :C:
H3C
H3C
CH3
CH3
C=N:
C-CH2
H3C
>
H3C
H3C
C=N:
Transcribed Image Text:The following two sets of reactions [(a) and (b)] show possibilities for arrow pushing in individual reaction steps. Identify which is wrong and explain why. Then using arrow pushing correctly, label which molecule is the nucleophile and which is the electrophile. (b) (a) H-CI: . .- :O: :Ö: H3C H3C CH3 C=N C-CH3 + :CI: H3C CH3 H3C CH2 H3C H3C ":C=N: H-CI: H3C I+ C-CH3 + :C: H3C H3C CH3 CH3 C=N: C-CH2 H3C > H3C H3C C=N:
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