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. Next, using the correct arrow pushing, label which molecule is the nucleophile and which is the electrophile. (a) (b) H3C +1. C-CH3 Cl: H3C H3C-CI →:I–CH3 + :Cl: C-CI: H3C/ H3C H3C H,C-Cl: :I-CH3 + :CI: : I :* H3C C-CI: H3C/ H3C :Cl: C-CH3 > H3C H3C

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 17MP
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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. Next, using the correct arrow pushing, label which molecule is the
nucleophile and which is the electrophile.
(a)
(b)
H3C
:Cl:
H3C
H,c-i: –
→: I-CH3 + :Cl:
C-C:
H3C /
H3C
H3C-Cl:
C-CH3
H3C
: H,C-Cl:
H3C-CI:
→: I-CH3 + :Cl:
H3C
:Cl:
H3C
C-CH3
C-CI:
H3C/
H3C
H3C
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. Next, using the correct arrow pushing, label which molecule is the nucleophile and which is the electrophile. (a) (b) H3C :Cl: H3C H,c-i: – →: I-CH3 + :Cl: C-C: H3C / H3C H3C-Cl: C-CH3 H3C : H,C-Cl: H3C-CI: →: I-CH3 + :Cl: H3C :Cl: H3C C-CH3 C-CI: H3C/ H3C H3C
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